Apigenin

Identification

Name
Apigenin
Accession Number
DB07352
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
LY-080400 / NSC-83244 / UCCF-031
Categories
UNII
7V515PI7F6
CAS number
520-36-5
Weight
Average: 270.2369
Monoisotopic: 270.05282343
Chemical Formula
C15H10O5
InChI Key
KZNIFHPLKGYRTM-UHFFFAOYSA-N
InChI
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZNot AvailableHelicobacter pylori
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0002124
KEGG Compound
C01477
PubChem Compound
5280443
PubChem Substance
99443823
ChemSpider
4444100
BindingDB
7458
ChEBI
18388
ChEMBL
CHEMBL28
IUPHAR
4136
Guide to Pharmacology
GtP Drug Page
HET
AGI
Wikipedia
Apigenin
PDB Entries
3amy / 3cf9 / 4der / 4dgm / 4hkk / 4wo0 / 5auv / 5i2h / 5uqt

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.118 mg/mLALOGPS
logP3.07ALOGPS
logP2.71ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.63ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.91 m3·mol-1ChemAxon
Polarizability26.78 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9887
Blood Brain Barrier+0.6364
Caco-2 permeable+0.8541
P-glycoprotein substrateNon-substrate0.5073
P-glycoprotein inhibitor INon-inhibitor0.9543
P-glycoprotein inhibitor IINon-inhibitor0.7525
Renal organic cation transporterNon-inhibitor0.9037
CYP450 2C9 substrateNon-substrate0.7813
CYP450 2D6 substrateNon-substrate0.9126
CYP450 3A4 substrateNon-substrate0.6907
CYP450 1A2 substrateInhibitor0.9222
CYP450 2C9 inhibitorInhibitor0.7746
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.7043
CYP450 3A4 inhibitorInhibitor0.958
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7316
Ames testNon AMES toxic0.8906
CarcinogenicityNon-carcinogens0.9181
BiodegradationNot ready biodegradable0.8384
Rat acute toxicity2.6983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9559
hERG inhibition (predictor II)Non-inhibitor0.9098
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-MS (3 TMS)GC-MSsplash10-00di-0000900000-b6d7fc88c039e719d164
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-0433900000-b411d851fccc9f228d84
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-03xv-1913500000-be46740b1210f9e106ee
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-0000900000-b6d7fc88c039e719d164
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 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-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-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-0f608530bf761944dbf3
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-0c659ac43b543480168b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0690000000-e19eed49b8311d9cd339
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0910000000-57a56bfe2cce55357a11
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-b8799a618cff0ac84ddb
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0490000000-f9a416c79166c84ca773
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-1499c7f2bceeb3e13f52
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0490000000-413a7da79773bc92a112
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0090000000-8f4d30104539ae85cd50
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0290000000-32e8793c17b364eee127
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uea-0900000000-52147353f7af35162dab
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0090000000-7a9b77ceb393c9239412
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00vi-0290000000-c9cb9331a28763da83a8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014i-0940000000-eb8b08c7beca627dc728
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-47dcd836edc83106c566
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-f81b58efeb7a6ad517b7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-9ee52d5a554d161d358d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0970000000-f0c48df94377a366e7cf
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-30ebb05b6bde04f3e31b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-a85299a573dffafef065
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uk9-1930000000-43094873af4b4f7a25b2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0290000000-ff8b597db51ea98fdc32
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0290000000-3406e459293197b27907
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0v4i-3910000000-3572b48dde802358120c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-ff3722aa39210cc9881e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0290000000-ed84e69abb42359dd823
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0uk9-0790000000-297c255e89289169aef5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3970000000-5a23944b045cfe1763b1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0090000000-781e82fec625cdc0aed5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0390000000-a31cd1b164f7c27a052f

Taxonomy

Description
This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavones
Direct Parent
Flavones
Alternative Parents
7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / Chromones / Pyranones and derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Vinylogous acids / Heteroaromatic compounds
show 4 more
Substituents
4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Flavone / Hydroxyflavonoid / Chromone / Benzopyran / 1-benzopyran / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
trihydroxyflavone (CHEBI:18388) / flavones, Flavones and Flavonols (C01477) / Flavones and Flavonols (LMPK12110005)

Targets

Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activity
Specific Function
Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs.Involved in unsaturat...
Gene Name
fabZ
Uniprot ID
Q5G940
Uniprot Name
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ
Molecular Weight
18184.08 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]

Drug created on September 15, 2010 15:20 / Updated on October 01, 2018 14:21