General Information of Drug (ID: DMQ4Z6E)

Drug Name
ISORHAMNETIN
Synonyms
Isorhamnetin; 480-19-3; 3-Methylquercetin; Isorhamnetol; 3'-Methoxyquercetin; 3'-Methoxy-3,4',5,7-tetrahydroxyflavone; isorhamnetine; 3'-Methylquercetin; C.I. 75680; 3-Methylquercetine; UNII-07X3IB4R4Z; CCRIS 3791; C16H12O7; EINECS 207-545-5; Flavone, 3'-methoxy-3,4',5,7-tetrahydroxy-; BRN 0044723; 3,5,7,4'-Tetrahydroxy-3'-methoxyflavone; CHEMBL379064; CHEBI:6052; 07X3IB4R4Z
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): 0 Molecular Weight (mw) 316.26
Logarithm of the Partition Coefficient (xlogp) 1.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C16H12O7
IUPAC Name
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Canonical SMILES
COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
InChI
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
InChIKey
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5281654
ChEBI ID
CHEBI:6052
CAS Number
480-19-3
UNII
07X3IB4R4Z
DrugBank ID
DB16767
TTD ID
D07YDN

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cytochrome P450 1B1 (CYP1B1) TTI84H7 CP1B1_HUMAN Inhibitor [1]
Plasmodium Enoyl-ACP reductase (Malaria fabI) TTNX2CS Q965D5_PLAFA Inhibitor [2]
Plasmodium Oxoacyl-[acyl-carrier protein] reductase (Malaria fabG) TTBE4IR Q965D6_PLAFA Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [3]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [4]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [3]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [3]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [3]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [5]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [4]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Protein Interaction/Cellular Processes [6]
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Protein Interaction/Cellular Processes [6]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
2 Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
3 Isorhamnetin inhibits proliferation and invasion and induces apoptosis through the modulation of peroxisome proliferator-activated receptor activation pathway in gastric cancer. J Biol Chem. 2012 Nov 2;287(45):38028-40. doi: 10.1074/jbc.M112.388702. Epub 2012 Sep 19.
4 3-Hydroxyflavone and structural analogues differentially activate pregnane X receptor: Implication for inflammatory bowel disease. Pharmacol Res. 2015 Oct;100:64-72.
5 Modulation of CYP1B1 and CYP1A1 gene expression and activation of aryl hydrocarbon receptor by Ginkgo biloba extract in MCF-10A human mammary epithelial cells. Can J Physiol Pharmacol. 2009 Sep;87(9):674-83. doi: 10.1139/y09-061.
6 Estrogenic activities of Ginkgo biloba extracts. Life Sci. 2004 Jan 30;74(11):1325-35. doi: 10.1016/j.lfs.2003.06.045.