Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0808)
Drug Name
Hesperetin
Synonyms
Cyanidanon 4'-methyl ether 1626; Hesperitin; Prestwick_908; Q9Q3D557F1; hesperetin; (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one; (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone; (S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one; 3',5,7-Trihydroxy-4'-methoxyflavanone; 5,7,3'-Trihydroxy-4'-methoxyflavanone; 520-33-2; AIONOLUJZLIMTK-AWEZNQCLSA-N; CHEBI:28230; EINECS 208-290-2; MFCD00075646; NSC 57654; UNII-Q9Q3D557F1; YSO2
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 302.28 Topological Polar Surface Area 96.2
Heavy Atom Count 22 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
72281
PubChem SID
4847 ; 597194 ; 877412 ; 8149172 ; 8195111 ; 10321847 ; 11112384 ; 11112385 ; 11336214 ; 11361453 ; 11363075 ; 11365637 ; 11368199 ; 11372127 ; 11375448 ; 11376361 ; 11462425 ; 11466152 ; 11467272 ; 11485481 ; 11485843 ; 11489609 ; 11490919 ; 11493749 ; 11493995 ; 11537620 ; 16889621 ; 24895619 ; 26613332 ; 26680108 ; 26744164 ; 26754195 ; 26754196 ; 29204220 ; 43128472 ; 46507998 ; 47365297 ; 47365298 ; 47440361 ; 47515405 ; 47515406 ; 47885508 ; 47959861 ; 48035231 ; 48110539 ; 48259342 ; 48421825 ; 49698360 ; 50069543 ; 50091682
ChEBI ID
ChEBI:28230
CAS Number
520-33-2
TTD Drug ID
D07MGA
Formula
C16H14O6
Canonical SMILES
COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1
InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Eriodictyol DM003394
440735
Oxidation - 4'-demethylation 1 [3]
Hesperetin 3p-O-Glucuronide DM006525
101644602
Conjugation - Glucuronidation 1 [4] , [5]
Hesperetin 7-O-glucuronide DM006526
71777476
Conjugation - Glucuronidation 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007030 Hesperetin Eriodictyol Oxidation - 4'-demethylation CYP1A2 [3]
MR007031 Hesperetin Hesperetin 3p-O-Glucuronide Conjugation - Glucuronidation UGT1A9 [4], [5]
MR007032 Hesperetin Hesperetin 7-O-glucuronide Conjugation - Glucuronidation UGT1A9 [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
References
1 The citrus flavanone hesperetin preferentially inhibits slow-inactivating currents of a long QT syndrome type 3 syndrome Na+ channel mutation. Br J Pharmacol. 2019 Apr;176(8):1090-1105.
2 In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem Toxicol. 2002 May;40(5):609-16.
3 DrugBank(Pharmacology-Metabolism):Hesperetin
4 BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification
5 Molecular mechanism of hesperetin-7-O-glucuronide, the main circulating metabolite of hesperidin, involved in osteoblast differentiation

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