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

General Information of Drug (ID: DR3167)
Drug Name
PIPERINE
Synonyms
piperine; 94-62-2; 1-Piperoylpiperidine; Piperin; Bioperine; Piperoylpiperidine; (E,E)-1-piperoylpiperidine; N-[(E,E)-Piperoyl]piperidine; Piperidine, 1-piperoyl-, (E,E)-; UNII-U71XL721QK; FEMA No. 2909; CCRIS 5572; Piperine (aliphatic); 1-Piperoylpiperidine, (E,E)-; 7780-20-3; C17H19NO3; EINECS 202-348-0; NSC 21727; 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine; N-(E,E)-piperoyl-piperidine; CHEMBL43185; U71XL721QK; CHEBI:28821; MXXWOMGUGJBKIW-YPCIICBESA-N; NSC21727; piperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)
Indication Vitiligo [ICD11: ED63] Phase 1/2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 285.34 Topological Polar Surface Area 38.8
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
638024
ChEBI ID
CHEBI:28821
CAS Number
94-62-2
TTD Drug ID
D0H7PW
Formula
C17H19NO3
Canonical SMILES
C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
InChI
InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
InChIKey
MXXWOMGUGJBKIW-YPCIICBESA-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
Piperine C11,15,16,18 DM019596 N. A. Oxidation - Hydroxylation 1 [3]
Piperine C12 DM015792
11983343
Oxidation - Oxidation 1 [3]
Piperine C19 DM019598 N. A. Reduction - Decarboxylation 1 [3]
Piperine C1,2 DM019594 N. A. Oxidation - Hydroxylation 2 [3]
Piperine C17 DM019595 N. A. Oxidation - Methylation 2 [3]
Piperine C20 DM019597 N. A. Other reaction - Dehydration 2 [3]
Piperine C5,6 DM019591 N. A. Conjugation - GSH conjugation 2 [3]
Piperine C7,9 DM019593 N. A. Unclear - Unclear 2 [3]
Piperine C8 DM019592 N. A. Reduction - Decarboxylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012251 Piperine Piperine C12 Oxidation - Oxidation Unclear [3]
MR012257 Piperine Piperine C11,15,16,18 Oxidation - Hydroxylation Unclear [3]
MR012259 Piperine Piperine C19 Reduction - Decarboxylation Unclear [3]
MR012258 Piperine C11,15,16,18 Piperine C20 Other reaction - Dehydration Unclear [3]
MR012252 Piperine C12 Piperine C5,6 Conjugation - GSH conjugation Unclear [3]
MR012254 Piperine C12 Piperine C7,9 Unclear - Unclear Unclear [3]
MR012255 Piperine C12 Piperine C1,2 Oxidation - Hydroxylation Unclear [3]
MR012256 Piperine C12 Piperine C17 Oxidation - Methylation Unclear [3]
MR012253 Piperine C5,6 Piperine C8 Reduction - Decarboxylation Unclear [3]
⏷ Show the Full List of 9 MR(s)
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 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2489).
2 GABA(A) receptor activity modulating piperine analogs: In vitro metabolic stability, metabolite identification, CYP450 reaction phenotyping, and protein binding
3 Piperine and Its Metabolite's Pharmacology in Neurodegenerative and Neurological Diseases

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