Details of the Drug

General Information of Drug (ID: DMLRNV2)

Drug Name

AMENTOFLAVONE

Synonyms

Amentoflavone; 1617-53-4; 3',8''-Biapigenin; Didemethyl-ginkgetin; Amenthoflavone; UNII-9I1VC79L77; MLS000574827; CHEBI:2631; 9I1VC79L77; SMR000156235; Q-100192; 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

538.5

Logarithm of the Partition Coefficient (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C30H18O10
IUPAC Name: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
InChI: InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChIKey: YUSWMAULDXZHPY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5281600
ChEBI ID: CHEBI:2631
CAS Number: 1617-53-4
TTD ID: D06HRX

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor alpha-1 (GABRA1)	TT1MPAY	GBRA1_HUMAN	Inhibitor	[1]
GABA(A) receptor alpha-2 (GABRA2)	TTBMV1G	GBRA2_HUMAN	Inhibitor	[1]
GABA(A) receptor alpha-3 (GABRA3)	TT37EDJ	GBRA3_HUMAN	Inhibitor	[1]
GABA(A) receptor alpha-5 (GABRA5)	TTNZPQ1	GBRA5_HUMAN	Inhibitor	[1]
GABA(A) receptor beta-2 (GABRB2)	TTZA1NY	GBRB2_HUMAN	Inhibitor	[1]
GABA(A) receptor gamma-2 (GABRG2)	TT06RH5	GBRG2_HUMAN	Inhibitor	[1]
Gamma-aminobutyric acid receptor (GAR)	TTNJYV2	NOUNIPROTAC	Inhibitor	[1]
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1)	TTL53M6	MCL1_HUMAN	Inhibitor	[2]
Xanthine dehydrogenase/oxidase (XDH)	TT7RJY8	XDH_HUMAN	Inhibitor	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[4]
L-dopachrome tautomerase (DCT)	OTYVNTBG	TYRP2_HUMAN	Gene/Protein Processing	[5]
Nitric oxide synthase, inducible (NOS2)	OTKKIOJ1	NOS2_HUMAN	Gene/Protein Processing	[6]
Prostaglandin G/H synthase 2 (PTGS2)	OT75U9M4	PGH2_HUMAN	Gene/Protein Processing	[6]
Prostaglandin-H2 D-isomerase (PTGDS)	OT71NN7C	PTGDS_HUMAN	Protein Interaction/Cellular Processes	[7]
Sterol regulatory element-binding protein 1 (SREBF1)	OTWBRPAI	SRBP1_HUMAN	Gene/Protein Processing	[8]
Tyrosinase	OTX54MAA	TYRO_HUMAN	Gene/Protein Processing	[5]
UDP-glucuronosyltransferase 1-6	OTGTQ2C9	UD16_HUMAN	Gene/Protein Processing	[9]
UDP-glucuronosyltransferase 1A1	OTH1C8OJ	UD11_HUMAN	Gene/Protein Processing	[9]
UDP-glucuronosyltransferase 1A10	OTOTZVEY	UD110_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4.
2	In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
3	Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
4	Inhibition of human cytochrome CYP 1 enzymes by flavonoids of StJohn's wort. Toxicology. 2006 Jan 16;217(2-3):194-205.
5	New constituent from Podocarpus macrophyllus var. macrophyllus shows anti-tyrosinase effect and regulates tyrosinase-related proteins and mRNA in human epidermal melanocytes. Chem Pharm Bull (Tokyo). 2007 May;55(5):757-61. doi: 10.1248/cpb.55.757.
6	Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line. Prostaglandins Leukot Essent Fatty Acids. 2002 May-Jun;66(5-6):485-92.
7	In silico prediction of prostaglandin D2 synthase inhibitors from herbal constituents for the treatment of hair loss. J Ethnopharmacol. 2015 Dec 4;175:470-80. doi: 10.1016/j.jep.2015.10.005. Epub 2015 Oct 9.
8	Amentoflavone prevents ox-LDL-induced lipid accumulation by suppressing the PPAR/CD36 signal pathway. Toxicol Appl Pharmacol. 2021 Nov 15;431:115733. doi: 10.1016/j.taap.2021.115733. Epub 2021 Sep 29.
9	Amentoflavone is a potent broad-spectrum inhibitor of human UDP-glucuronosyltransferases. Chem Biol Interact. 2018 Mar 25;284:48-55.