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]
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) 5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 10
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
CHEMBL63354
CAS Number
1617-53-4
TTD ID
D06HRX
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
L-dopachrome tautomerase (DCT) OTYVNTBG TYRP2_HUMAN Gene/Protein Processing [4]
Prostaglandin-H2 D-isomerase (PTGDS) OT71NN7C PTGDS_HUMAN Protein Interaction/Cellular Processes [5]
Tyrosinase OTX54MAA TYRO_HUMAN Gene/Protein Processing [4]
UDP-glucuronosyltransferase 1-6 OTGTQ2C9 UD16_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A10 OTOTZVEY UD110_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A4 OT4PU620 UD14_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A7 OTY4JJ32 UD17_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A8 OTTMABBG UD18_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) 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 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.
5 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.
6 Amentoflavone is a potent broad-spectrum inhibitor of human UDP-glucuronosyltransferases. Chem Biol Interact. 2018 Mar 25;284:48-55.