Identification

Name
Naringenin
Accession Number
DB03467  (EXPT02295)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
HN5425SBF2
CAS number
480-41-1
Weight
Average: 272.2528
Monoisotopic: 272.068473494
Chemical Formula
C15H12O5
InChI Key
FTVWIRXFELQLPI-ZDUSSCGKSA-N
InChI
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
IUPAC Name
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
SMILES
[H][[email protected]]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHTH-type transcriptional regulator TtgRNot AvailablePseudomonas putida (strain DOT-T1E)
UEstrogen receptor alphaNot AvailableHuman
UAldo-keto reductase family 1 member C1
antagonist
Human
UCytochrome P450 1B1Not AvailableHuman
UKAT8 regulatory NSL complex subunit 3Not AvailableHuman
USex hormone-binding globulinNot AvailableHuman
UCytochrome P450 19A1
inhibitor
Human
UEstrogen receptor beta
partial agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Naringenin.Approved
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Naringenin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Naringenin.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Naringenin.Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Naringenin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Naringenin.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Naringenin.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Naringenin.Approved
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Naringenin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Naringenin.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Naringenin.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Naringenin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Naringenin.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Naringenin.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Naringenin.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Naringenin.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Heike Wilhelm, Ludger A. Wessojohann, Martin Biendl, "METHOD FOR PRODUCING NARINGENIN DERIVATIVES FROM XANTHOHUMOL." U.S. Patent US20090227806, issued September 10, 2009.

US20090227806
General References
Not Available
External Links
Human Metabolome Database
HMDB02670
KEGG Compound
C00509
PubChem Compound
439246
PubChem Substance
46508043
ChemSpider
388383
BindingDB
23419
ChEBI
17846
ChEMBL
CHEMBL9352
PharmGKB
PA151958361
HET
NAR
PDB Entries
1cgk / 1eyq / 2brt / 2uxu / 4a87 / 4d06 / 4deu / 4eh3

Clinical Trials

Clinical Trials
Not Available

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)251 °CPhysProp
logP2.52PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.214 mg/mLALOGPS
logP2.47ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.29 m3·mol-1ChemAxon
Polarizability27.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.967
Blood Brain Barrier+0.6794
Caco-2 permeable+0.7533
P-glycoprotein substrateSubstrate0.5458
P-glycoprotein inhibitor INon-inhibitor0.9638
P-glycoprotein inhibitor IINon-inhibitor0.8859
Renal organic cation transporterNon-inhibitor0.8949
CYP450 2C9 substrateNon-substrate0.7425
CYP450 2D6 substrateNon-substrate0.8691
CYP450 3A4 substrateNon-substrate0.6294
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.7463
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.8988
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7121
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9364
BiodegradationNot ready biodegradable0.7934
Rat acute toxicity3.5110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.8832
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-MSsplash10-00fs-1951400000-0e93ea96a72cb2a5a868
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0a4r-2961300000-725a9d843a4286e86b06
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00fs-1951400000-0e93ea96a72cb2a5a868
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4r-2961300000-725a9d843a4286e86b06
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00fs-1951400000-44c9c035aeffcacf4e8c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004l-1931100000-ec4d00bbd2895d4d5f9c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a4r-2961300000-6cd5d798a9dad326f771
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-00di-0190000000-ba73aef4d7cf20a2777d
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-066r-3900000000-98ba56d82461a2dc7f6f
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-02t9-9600000000-005d5eb55c1f6f3b893d
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, PositiveLC-MS/MSsplash10-00di-0090000000-87dba9fe511299bf27e8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, PositiveLC-MS/MSsplash10-00di-0090000000-52282430f89f3cfd51ff
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0g4i-1960000000-74e384d175dd4f05938c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-014i-1900000000-702ce5f0315e56bb08a0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0udi-2900000000-aeb81b324d8162537df3
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0fk9-1960000000-b4a541e5476f88624522
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 25V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 25V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0090000000-c9932e611eee004227d2
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0fk9-0790000000-01d21d6049f2491536ae
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uxr-0900000000-cabe5e8a523a3dead758
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-a41225d5baa6cee98b04
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-d8ee697bae1e5b5e71a8
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0g4i-1960000000-74e384d175dd4f05938c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-1900000000-702ce5f0315e56bb08a0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0900000000-6cdfb6c148fb435698b6
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0900000000-909bef3dfb9026c131f7
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0091410000-37f0ba8d8adfca457614
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0091410000-7652d0ea57e1bd750c0d
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-2290000000-12b67201652bda7cc143
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-3390000000-9032465ab9e27fb64222
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0900000000-925ed77c316b6b498fd4
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0900000000-3c3dfed30d5bf82a86ed
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0090000000-7294a338c82caa7db111
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0090000000-0574836f71b4ae50b0f4
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0090000000-8c13464bba0487b025d2
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0gb9-0900000000-5295f7ce31d20a80235c
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0900000000-cf1a906caa2c625f5426
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00di-0090000000-8f18a8cf32f1d24745d1
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0900000000-bfa606b2e93e4b1d2801
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0uk9-0930000000-9a38a8949493a958cc14
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-1e1274431dfd687a79d9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0890000000-db8e41c6e40456a52d1d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-0c53618e3ff69040cf89
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-7983cc27d698c577209c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-ef2de5a88c59af9141ac
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-2900000000-aeb81b324d8162537df3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-1960000000-b4a541e5476f88624522
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udj-0900000000-378404aeeebe6a8cb96d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udj-0900000000-a14308e7b8403f151bd6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-159045cc0fe4ba5716f6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-9243b8df08163571558d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00kf-0390000000-975b1452a3ddf651e100
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00kf-0390000000-ca245d6eefb5d79feb84
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-002f-0000930000-6211f20dedf500cc8612
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-002f-0000940000-0018133c751d7b418518
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03dr-0006290000-d434ab0a7eaefb5d6810
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01p9-0005290000-c35b6c3ca8da75c45b8b
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 flavanones. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavans
Direct Parent
Flavanones
Alternative Parents
7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / Chromones / Aryl alkyl ketones / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Vinylogous acids
show 3 more
Substituents
Flavanone / Hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Chromone / Benzopyran / Chromane / 1-benzopyran / Aryl alkyl ketone
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
naringenin (CHEBI:17846) / flavanones (C00509) / Flavanones (LMPK12140001)

Targets

Kind
Protein
Organism
Pseudomonas putida (strain DOT-T1E)
Pharmacological action
Unknown
General Function
Dna binding
Specific Function
Represses expression from the ttgABC operon promoter and its own expression. Binds to a promoter region between the divergently transcribed ttgR and ttgABC genes/operons; in the presence of chloram...
Gene Name
ttgR
Uniprot ID
Q9AIU0
Uniprot Name
HTH-type transcriptional regulator TtgR
Molecular Weight
23854.075 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
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. Hunter DS, Hodges LC, Vonier PM, Fuchs-Young R, Gottardis MM, Walker CL: Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium. Cancer Res. 1999 Jul 1;59(13):3090-9. [PubMed:10397250]
  2. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [PubMed:9751507]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
Gene Name
AKR1C1
Uniprot ID
Q04828
Uniprot Name
Aldo-keto reductase family 1 member C1
Molecular Weight
36788.02 Da
References
  1. Brozic P, Smuc T, Gobec S, Rizner TL: Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1. Mol Cell Endocrinol. 2006 Oct 19;259(1-2):30-42. Epub 2006 Sep 8. [PubMed:16962702]
Details
4. Cytochrome P450 1B1
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
As part of the NSL complex it is involved in acetylation of nucleosomal histone H4 on several lysine residues and therefore may be involved in the regulation of transcription.
Specific Function
Not Available
Gene Name
KANSL3
Uniprot ID
Q9P2N6
Uniprot Name
KAT8 regulatory NSL complex subunit 3
Molecular Weight
95990.725 Da
References
  1. Priscilla DH, Roy D, Suresh A, Kumar V, Thirumurugan K: Naringenin inhibits alpha-glucosidase activity: a promising strategy for the regulation of postprandial hyperglycemia in high fat diet fed streptozotocin induced diabetic rats. Chem Biol Interact. 2014 Mar 5;210:77-85. doi: 10.1016/j.cbi.2013.12.014. Epub 2014 Jan 8. [PubMed:24412302]
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]
Details
7. Cytochrome P450 19A1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Kao YC, Zhou C, Sherman M, Laughton CA, Chen S: Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study. Environ Health Perspect. 1998 Feb;106(2):85-92. [PubMed:9435150]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial agonist
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. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [PubMed:9751507]

Transporters

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. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378]
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. Takanaga H, Ohnishi A, Matsuo H, Sawada Y: Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells. Biol Pharm Bull. 1998 Oct;21(10):1062-6. [PubMed:9821810]
  2. Eagling VA, Profit L, Back DJ: Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol. 1999 Oct;48(4):543-52. [PubMed:10583025]
  3. Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ: Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604. [PubMed:14980703]
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. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. [PubMed:11306701]
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. 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]
  2. 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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:28