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

General Information of Drug (ID: DR2989)
Drug Name
Perillyl alcohol
Synonyms Monoterpenes, University of Wisconsin; Perillyl alcohol, University of Wisconsin; Perillyl alcohol, WARF
Indication Solid tumour/cancer [ICD11: 2A00-2F9Z] Discontinued in Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 152.23 Topological Polar Surface Area 20.2
Heavy Atom Count 11 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
10819
ChEBI ID
CHEBI:15420
CAS Number
536-59-4
TTD Drug ID
D0S2HO
Formula
C10H16O
Canonical SMILES
CC(=C)C1CCC(=CC1)CO
InChI
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
InChIKey
NDTYTMIUWGWIMO-UHFFFAOYSA-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
Dehydroperillic acid DM015064
72620
Unclear - Unclear 1 [6]
Perillaldehyde (PCO) DM014972
16441
Oxidation - Oxidation 1 [3]
Perillic acid (PCOOH) DM015518
9543109
Oxidation - Oxidation 2 [3]
3-(Dihydroxyphenyl)propanoic acid DM015268
348154
Unclear - Unclear 3 [7]
Cis-Dihydroperillic Acid DM015268
381256
Unclear - Unclear 3 [7]
Perillyl-CoA DM017821 N. A. Unclear - Unclear 3 [2]
2-hydroxy-4-isopropenyl-cyclohexane-1-carboxyl-CoA DM017822 N. A. Unclear - Unclear 4 [2]
4-isopropenyl-2-oxo-cyclohexane-1-carboxyl-CoA DM017823 N. A. Unclear - Unclear 5 [2]
3-isopropenyl-pimelyl-CoA DM017824 N. A. Unclear - Unclear 6 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012995 Perillyl alcohol Perillaldehyde (PCO) Oxidation - Oxidation ALDH [3]
MR013002 Perillyl alcohol Dehydroperillic acid Unclear - Unclear Unclear [6]
MR012996 Perillaldehyde (PCO) Perillic acid (PCOOH) Oxidation - Oxidation ALDH [3]
MR012997 Perillic acid (PCOOH) Perillyl-CoA Unclear - Unclear BN940_14101 [2]
MR013001 Perillic acid (PCOOH) Cis-Dihydroperillic Acid Unclear - Unclear Unclear [7]
MR012998 Perillyl-CoA 2-hydroxy-4-isopropenyl-cyclohexane-1-carboxyl-CoA Unclear - Unclear BN940_14026 [2]
MR012999 2-hydroxy-4-isopropenyl-cyclohexane-1-carboxyl-CoA 4-isopropenyl-2-oxo-cyclohexane-1-carboxyl-CoA Unclear - Unclear MrcD [2]
MR013000 4-isopropenyl-2-oxo-cyclohexane-1-carboxyl-CoA 3-isopropenyl-pimelyl-CoA Unclear - Unclear MrcE [2]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
2-hydroxy-4-isopropenylcyclohexane-1-carboxyl-CoA dehydrogenase (MrcD) DMEN791 Castellaniella defragrans 65Phen Not Available Not Available [2]
4-isopropenyl-2-oxocyclohexane-1-carboxyl-CoA hydrolase (MrcE) DMEN792 Castellaniella defragrans 65Phen Not Available Not Available [2]
Aldehyde dehydrogenase (ALDH) DMEN076 . Not Available Not Available [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Perillic acid-CoA ligase GeoC (BN940_14101) DMEN789 Castellaniella defragrans 65Phen
W8X9R1_CASDE
6.2.1.3
[2]
perillyl-CoA hydratase (BN940_14026) DMEN790 Castellaniella defragrans 65Phen
W8X9Q8_CASDE
1.1.1.35
[2]
⏷ Show the Full List of 8  DME(s)
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004297)
2 The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen
3 Cytotoxicity and biotransformation of the anticancer drug perillyl alcohol in PC12 cells and in the rat
4 In vivo production of novel vitamin D2 hydroxy-derivatives by human placentas, epidermal keratinocytes, Caco-2 colon cells and the adrenal gland. Mol Cell Endocrinol. 2014 Mar 5;383(1-2):181-92. doi: 10.1016/j.mce.2013.12.012.
5 Identification of Selective CYP3A7 and CYP3A4 Substrates and Inhibitors Using a High-Throughput Screening Platform. Front Pharmacol. 2022 Jul 1;13:899536. doi: 10.3389/fphar.2022.899536.
6 Cytotoxic, Antiproliferative and Apoptotic Effects of Perillyl Alcohol and Its Biotransformation Metabolite on A549 and HepG2 Cancer Cell Lines
7 Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma

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