Identification

Name
Genistein
Accession Number
DB01645  (EXPT01582)
Type
Small Molecule
Groups
Investigational
Description

An isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines.

Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in Felmingia vestita, which is a plant traditionally used against worms. It has also been demonstrated to be effective against intestinal parasites such as the common liver fluke, pork trematode and poultry cestode. [Wikipedia]

Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women [1].

Genistein can be found in food sources such as tofu, fava beans, soybeans, kudzu, and lupin. It is also present in certain cell cultures and medicinal plants. [Wikipedia]

Structure
Thumb
Synonyms
  • 4',5, 7-Trihydroxyisoflavone
  • 5,7,4'-Trihydroxyisoflavone
  • Genisteol
  • Genisterin
External IDs
FW-635I-2 / NPI-031L / NSC-36586 / SIPI-807-1
International/Other Brands
Prunetol / Sophoricol
Categories
UNII
DH2M523P0H
CAS number
446-72-0
Weight
Average: 270.2369
Monoisotopic: 270.05282343
Chemical Formula
C15H10O5
InChI Key
TZBJGXHYKVUXJN-UHFFFAOYSA-N
InChI
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
IUPAC Name
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
SMILES
OC1=CC=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2)C1=O

Pharmacology

Indication

Currently Genistein is being studied in clinical trials as a treatment for prostate cancer.

Pharmacodynamics
Not Available
Mechanism of action

Genistein may inhibit cancer cell growth by blocking enzymes required for cell growth.

Genistein may decrease cardiovascular risk in postmenopausal women by interacting with the nuclear estrogen receptors to alter the transcription of cell specific genes. In randomized clinical trials, genistein was seen to increase the ratio of nitric oxide to endothelin and improved flow-mediated endothelium dependent vasodilation in healthy postmenopausal women [1]. In addition, genistein may have beneficial effects on glucose metabolism by inhibiting islet tyrosine kinase activity as well as insulin release dependent on glucose and sulfonylurea [1].

TargetActionsOrganism
UEstrogen receptor betaNot AvailableHuman
UDNA topoisomerase 2-alphaNot AvailableHuman
UProtein-tyrosine kinase 2-betaNot AvailableHuman
UNuclear receptor coactivator 1Not AvailableHuman
UEstrogen receptor alphaNot AvailableHuman
UNuclear receptor coactivator 2Not AvailableHuman
USteroid hormone receptor ERR2
agonist
Human
USteroid hormone receptor ERR1
agonist
Human
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
URAC-alpha serine/threonine-protein kinaseNot AvailableHuman
UG-protein coupled estrogen receptor 1Not AvailableHuman
UCytochrome P450 1B1Not AvailableHuman
USex hormone-binding globulinNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
  • Helminthic Microorganisms
  • Parasitic nematodes and other roundworms
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Genistein.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Genistein.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Genistein.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Genistein.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Genistein.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Genistein.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Genistein.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Genistein.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Genistein.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Genistein.
Food Interactions
Not Available

References

Synthesis Reference

J. Mark Weber, Andreas Constantinou, Paul E. Hessler, "Process of preparing genistein." U.S. Patent US5554519, issued June, 1994.

US5554519
General References
  1. Crisafulli A, Altavilla D, Marini H, Bitto A, Cucinotta D, Frisina N, Corrado F, D'Anna R, Squadrito G, Adamo EB, Marini R, Romeo A, Cancellieri F, Buemi M, Squadrito F: Effects of the phytoestrogen genistein on cardiovascular risk factors in postmenopausal women. Menopause. 2005 Mar;12(2):186-92. [PubMed:15772566]
  2. Toner E, Brennan GP, Wells K, McGeown JG, Fairweather I: Physiological and morphological effects of genistein against the liver fluke, Fasciola hepatica. Parasitology. 2008 Sep;135(10):1189-203. doi: 10.1017/S0031182008004630. [PubMed:18771609]
External Links
Human Metabolome Database
HMDB0003217
KEGG Compound
C06563
PubChem Compound
5280961
PubChem Substance
46509060
ChemSpider
4444448
BindingDB
19459
ChEBI
28088
ChEMBL
CHEMBL44
Therapeutic Targets Database
DCL000330
PharmGKB
PA165109660
IUPHAR
2826
Guide to Pharmacology
GtP Drug Page
HET
GEN
Wikipedia
Genistein
PDB Entries
1qkm / 1x7j / 1x7r / 2qa8 / 3kgt / 3kgu / 4fj1 / 5auz / 5av4 / 5kda

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentCancer of Head and Neck1
1CompletedTreatmentMalignancies1
1, 2CompletedBasic ScienceCystic Fibrosis (CF)1
1, 2CompletedTreatmentColorectal Cancers / Malignant Neoplasm of Colon / Rectal Carcinoma1
1, 2CompletedTreatmentMalignancies1
1, 2TerminatedBasic ScienceCystic Fibrosis (CF)1
1, 2Unknown StatusTreatmentAdenocarcinomas1
2CompletedPreventionBone Diseases / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Depression / Heart Diseases / Myocardial Ischemia / One to five years postmenopausal / Osteoporosis1
2CompletedPreventionCancer, Breast1
2CompletedTreatmentAdenocarcinoma, Prostate / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer1
2CompletedTreatmentRecurrent Bladder Cancer / Stage I Bladder Cancer / Stage II Bladder Cancer / Stage III Bladder Cancer1
2RecruitingPreventionProstate Cancer1
2RecruitingSupportive CareChildhood Lymphoma / Childhood Solid Tumors / Ewing's Sarcoma (ES) / Germ Cell Tumors / Lymphoma, Hodgkins / Malignant Lymphomas / Medulloblastoma, Childhood / Medulloblastomas / Neoplasms, Brain / Neuroblastomas / Neuroectodermal Tumors, Primitive / Non-Hodgkin's Lymphoma (NHL) / Rhabdomyosarcomas / Soft Tissue Sarcoma (STS) / Tumors, Solid / Wilms' tumor1
2RecruitingTreatmentBladder Cancers1
2Unknown StatusBasic ScienceProstatic Neoplasms1
2, 3CompletedTreatmentCoronary Artery Disease1
2, 3CompletedTreatmentMenopause / Osteopenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)301.5 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.123 mg/mLALOGPS
logP3.04ALOGPS
logP3.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m3·mol-1ChemAxon
Polarizability26.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9877
Blood Brain Barrier+0.6785
Caco-2 permeable+0.7002
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9288
P-glycoprotein inhibitor IINon-inhibitor0.7828
Renal organic cation transporterNon-inhibitor0.9075
CYP450 2C9 substrateNon-substrate0.7672
CYP450 2D6 substrateNon-substrate0.9105
CYP450 3A4 substrateNon-substrate0.6821
CYP450 1A2 substrateInhibitor0.9254
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorInhibitor0.8881
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8009
Ames testNon AMES toxic0.9638
CarcinogenicityNon-carcinogens0.9276
BiodegradationNot ready biodegradable0.8572
Rat acute toxicity3.2988 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9569
hERG inhibition (predictor II)Non-inhibitor0.8917
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-0321900000-1dd6fcaf99898bd949df
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-0321900000-1dd6fcaf99898bd949df
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-014l-9600000000-04b546320e268d817276
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-00kf-5910000000-7e265d1b4640f882195a
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-0v4m-1960000000-7843ec8ae23314f88147
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-00di-0290000000-52ec910b223a3688fbc0
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-00di-0190000000-4045f471e10774927fb0
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-00di-0090000000-b593f863241cb83cbaa8
LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , PositiveLC-MS/MSsplash10-00di-0190000000-0cd8d123608bd54f7214
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, PositiveLC-MS/MSsplash10-00di-0090000000-9ce354d07dc39313259b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0910000000-5eb75a138568fa4ac897
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0fr6-2920000000-a32f6ae97952bb96de05
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-0290000000-4592d557e739a114cbfa
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , PositiveLC-MS/MSsplash10-00di-0090000000-14ae481944ad1a1f7ca0
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , NegativeLC-MS/MSsplash10-014i-0090030000-a3400b0a77da6983528f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0090000000-9542aa77ed8c84bed45f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0090000000-c6b607727a820f778924
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0190000000-420b0e9cca5700d25589
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0159-1950000000-e2dfe33be49873b2975d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-053r-3910000000-667af9dc5d8d490e2c6f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-5900000000-fc48254c3b9ccf779d62
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00lr-9800000000-cba29ca84271d6f980a5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9300000000-4150dab542ca3ac540a2
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9100000000-8d38036ee57ded4ff3fb
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0910000000-e781065a7305ca109957
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0090000000-ace47d8eb119a5d9801a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0090000000-9542aa77ed8c84bed45f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00lr-0890000000-a5611c3a49da154342cd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-003r-0970000000-5c1ad72d644a6f7d8fb2
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-01b9-0290000000-407d48606605aac4c975
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00xr-0290000000-4190acc65c88c8de1f75
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0090000000-149fc10384d69f21d066
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0090000000-4435ed9ac313efc90eb7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-05fs-0024940000-b0ddcf478891ad4cbdd1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00mk-0034930000-fbc3afe1a4dbbac9d6cf
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0fwa-0690000000-5f4232eecb2784e6f5fb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00xr-0190000000-946699244cd747e3497f
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00xr-0290000000-0807d3b38a6c6ff00fd1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00xr-0190000000-681483b261fd30dd2552
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-017i-0590000000-6f84f3906d9008564a3e
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-016r-0590000000-7051c8d7f65ebb16ee93
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0avi-0023930000-802e7b88659dcdcdc579
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0600-0024930000-63b03abb31868a4ad97d
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0090000000-0e3ca66534f635efb4d8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0900000000-ad50062f85b9c32e1426
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0910000000-6a694e60823635f66757
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0190000000-3a2edef598996d8ee33a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0090000000-ace47d8eb119a5d9801a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0090000000-9542aa77ed8c84bed45f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00lr-0890000000-a5611c3a49da154342cd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-003r-0970000000-5c1ad72d644a6f7d8fb2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-4274fbe3f25a7a4e1763
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0090000000-02a1637fcc9a07392ba3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0290000000-a60723328e71945659e4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0v4m-1960000000-5ac1d77b7f1d478f9382
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fr6-4910000000-f32b159fe5a08e29fdf8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kf-8900000000-197e5590fe8134de533b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9400000000-26d4739286bef040b4f9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9300000000-6d84c4f68b9adbb0190f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9200000000-c3580569c07b6affd7e1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-76a9cf3dd47ae8f37162
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0190000000-af442f78e868fd43ac61
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uxu-0940000000-c018563cc751d4f71058
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014l-4900000000-5490c0b819842ba4a872
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-2c1c9cb6dfc7a092d3a8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-125841d51722dcc61cba
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-124c837f947147cccd5c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0g4i-0390000000-32e5ad3ba5c1dab47e34
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uxu-0970000000-2cc2b429ddf3d4dc77f4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0190000000-8d8291787b0ec5d9dc5e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0390000000-f5674c252eb8da406041
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fk9-0490000000-3ed2edca3db41c24bf64
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-014l-9600000000-b15477d1806070aa2e1c
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00kf-5910000000-48f270af88a5a591e780
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-0v4m-1960000000-fbd7f2eb8c701be4e7a1
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00di-0290000000-6a2f647c28daa9287eab
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00di-0090000000-4045f471e10774927fb0
LC-MS/MS Spectrum - LC-APPI-QQ , positiveLC-MS/MSsplash10-00di-0090000000-b593f863241cb83cbaa8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fr6-2920000000-a32f6ae97952bb96de05
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0290000000-4592d557e739a114cbfa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0390000000-4954518a873e098a93ee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fr6-2920000000-e988d098144d69e2ab01
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0390000000-09228775cac3366ba894
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0790000000-752271144b920ef9dcdf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uxr-0980000000-f0891f193cb6d435f807
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uxr-0980000000-349ac43b6dcc1cf4102c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0970000000-779d5c079f78c275730e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uxr-0980000000-f150df5c0197922029f6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0059000000-34280291df8e4c7b04d8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0w2c-0890000000-9f6c64fa85b4817a9d2b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uxu-0890000000-bc869d53d009967db5ab
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uxu-0890000000-8d6c32fb0002461eb54a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0059000000-04d9ea7c483021a2d344
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0090000000-51b08ce91884b9a58e53
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0090000000-4ee95871dce63b9779ee
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0059000000-f80b6aba4e760b1e10b9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0009000000-71baf2b41ac3897b9b24
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0009000000-d57bb7c8267de895458d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01ox-0070090000-1b628a434e3f732dfd2c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01ox-0060090000-579c6bfa12c12e9d28cd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-1490000000-7e273097c726d64fddd7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fk9-0950000000-1d6e8433360fd3015619
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0490000000-8a8038ed373877790e4b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0190000000-49c573bd6b3218e32ec0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0390000000-4954518a873e098a93ee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fr6-2920000000-e988d098144d69e2ab01
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0390000000-09228775cac3366ba894
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uxr-0790000000-752271144b920ef9dcdf
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Isoflavonoids
Sub Class
Isoflav-2-enes
Direct Parent
Isoflavones
Alternative Parents
Hydroxyisoflavonoids / Chromones / Pyranones and derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Vinylogous acids / Heteroaromatic compounds / Oxacyclic compounds / Organooxygen compounds
show 2 more
Substituents
Hydroxyisoflavonoid / Isoflavone / Chromone / Benzopyran / 1-benzopyran / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Pyranone / Phenol / Monocyclic benzene moiety
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
7-hydroxyisoflavones (CHEBI:28088) / isoflavones, Isoflavonoids (C06563) / Isoflavonoids (LMPK12050218)

Targets

Details
1. Estrogen receptor beta
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Signal transducer activity
Specific Function
Non-receptor protein-tyrosine kinase that regulates reorganization of the actin cytoskeleton, cell polarization, cell migration, adhesion, spreading and bone remodeling. Plays a role in the regulat...
Gene Name
PTK2B
Uniprot ID
Q14289
Uniprot Name
Protein-tyrosine kinase 2-beta
Molecular Weight
115873.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Details
5. Estrogen receptor alpha
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
Gene Name
NCOA2
Uniprot ID
Q15596
Uniprot Name
Nuclear receptor coactivator 2
Molecular Weight
159155.645 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
Gene Name
ESRRB
Uniprot ID
O95718
Uniprot Name
Steroid hormone receptor ERR2
Molecular Weight
56207.085 Da
References
  1. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [PubMed:14638870]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and...
Gene Name
ESRRA
Uniprot ID
P11474
Uniprot Name
Steroid hormone receptor ERR1
Molecular Weight
45509.11 Da
References
  1. Suetsugi M, Su L, Karlsberg K, Yuan YC, Chen S: Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91. [PubMed:14638870]
  2. Chen S, Ye J, Kijima I, Kinoshita Y, Zhou D: Positive and negative transcriptional regulation of aromatase expression in human breast cancer tissue. J Steroid Biochem Mol Biol. 2005 May;95(1-5):17-23. [PubMed:15955695]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [PubMed:16054614]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine/tyrosine kinase activity
Specific Function
AKT1 is one of 3 closely related serine/threonine-protein kinases (AKT1, AKT2 and AKT3) called the AKT kinase, and which regulate many processes including metabolism, proliferation, cell survival, ...
Gene Name
AKT1
Uniprot ID
P31749
Uniprot Name
RAC-alpha serine/threonine-protein kinase
Molecular Weight
55686.035 Da
References
  1. Barve V, Ahmed F, Adsule S, Banerjee S, Kulkarni S, Katiyar P, Anson CE, Powell AK, Padhye S, Sarkar FH: Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells. J Med Chem. 2006 Jun 29;49(13):3800-8. [PubMed:16789737]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hormone binding
Specific Function
G-protein coupled estrogen receptor that binds to 17-beta-estradiol (E2) with high affinity, leading to rapid and transient activation of numerous intracellular signaling pathways. Stimulates cAMP ...
Gene Name
GPER1
Uniprot ID
Q99527
Uniprot Name
G-protein coupled estrogen receptor 1
Molecular Weight
42247.12 Da
References
  1. Thomas P, Dong J: Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J Steroid Biochem Mol Biol. 2006 Dec;102(1-5):175-9. Epub 2006 Nov 7. [PubMed:17088055]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, Yamazaki H, Guengerich FP, Komori M: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35. doi: 10.1021/tx100286d. [PubMed:21053930]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Hu M, Krausz K, Chen J, Ge X, Li J, Gelboin HL, Gonzalez FJ: Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. Drug Metab Dispos. 2003 Jul;31(7):924-31. [PubMed:12814970]
  2. Xu X, Duncan AM, Merz BE, Kurzer MS: Effects of soy isoflavones on estrogen and phytoestrogen metabolism in premenopausal women. Cancer Epidemiol Biomarkers Prev. 1998 Dec;7(12):1101-8. [PubMed:9865428]
  3. Shimada H, Eto M, Ohtaguro M, Ohtsubo M, Mizukami Y, Ide T, Imamura Y: Differential mechanisms for the inhibition of human cytochrome P450 1A2 by apigenin and genistein. J Biochem Mol Toxicol. 2010 Jul-Aug;24(4):230-4. doi: 10.1002/jbt.20328. [PubMed:20806393]
  4. Breinholt VM, Rasmussen SE, Brosen K, Friedberg TH: In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s. Pharmacol Toxicol. 2003 Jul;93(1):14-22. [PubMed:12828569]
  5. Daily Med, Genistein [Link]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Specific Function
Aromatase activity
Gene Name
Cyp1a1
Uniprot ID
P00185
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
59392.695 Da
References
  1. Xu X, Duncan AM, Merz BE, Kurzer MS: Effects of soy isoflavones on estrogen and phytoestrogen metabolism in premenopausal women. Cancer Epidemiol Biomarkers Prev. 1998 Dec;7(12):1101-8. [PubMed:9865428]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Substrate
General Function
Testosterone 6-beta-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
Cyp3a1
Uniprot ID
P04800
Uniprot Name
Cytochrome P450 3A1
Molecular Weight
57917.375 Da
References
  1. Jager W, Sartori M, Herzog W, Thalhammer T: Genistein metabolism in liver microsomes of Wistar and mutant TR(-)-rats. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):105-16. [PubMed:9644724]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Substrate
General Function
Testosterone 6-beta-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
Cyp3a2
Uniprot ID
P05183
Uniprot Name
Cytochrome P450 3A2
Molecular Weight
57731.215 Da
References
  1. Jager W, Sartori M, Herzog W, Thalhammer T: Genistein metabolism in liver microsomes of Wistar and mutant TR(-)-rats. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):105-16. [PubMed:9644724]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Xiao CQ, Chen R, Lin J, Wang G, Chen Y, Tan ZR, Zhou HH: Effect of genistein on the activities of cytochrome P450 3A and P-glycoprotein in Chinese healthy participants. Xenobiotica. 2012 Feb;42(2):173-8. doi: 10.3109/00498254.2011.615954. Epub 2011 Sep 26. [PubMed:21943317]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name
TTR
Uniprot ID
P02766
Uniprot Name
Transthyretin
Molecular Weight
15886.88 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Castro AF, Altenberg GA: Inhibition of drug transport by genistein in multidrug-resistant cells expressing P-glycoprotein. Biochem Pharmacol. 1997 Jan 10;53(1):89-93. [PubMed:8960067]
  2. Versantvoort CH, Rhodes T, Twentyman PR: Acceleration of MRP-associated efflux of rhodamine 123 by genistein and related compounds. Br J Cancer. 1996 Dec;74(12):1949-54. [PubMed:8980395]
  3. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Pec MK, Aguirre A, Fernandez JJ, Souto ML, Dorta JF, Villar J: Dehydrothyrsiferol does not modulate multidrug resistance-associated protein 1 resistance: a functional screening system for MRP1 substrates. Int J Mol Med. 2002 Nov;10(5):605-8. [PubMed:12373300]
  2. Nguyen H, Zhang S, Morris ME: Effect of flavonoids on MRP1-mediated transport in Panc-1 cells. J Pharm Sci. 2003 Feb;92(2):250-7. [PubMed:12532374]
  3. Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem Biophys Res Commun. 2003 Oct 10;310(1):222-7. [PubMed:14511674]
  4. Versantvoort CH, Rhodes T, Twentyman PR: Acceleration of MRP-associated efflux of rhodamine 123 by genistein and related compounds. Br J Cancer. 1996 Dec;74(12):1949-54. [PubMed:8980395]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Imai Y, Tsukahara S, Asada S, Sugimoto Y: Phytoestrogens/flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance. Cancer Res. 2004 Jun 15;64(12):4346-52. [PubMed:15205350]
  2. Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. [PubMed:15102949]
  3. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [PubMed:22541068]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:04