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

General Information of Drug (ID: DR1699)
Drug Name
NSC-122758
Synonyms
Afaxin; Agiolan; Agoncal; Alcovit A; Alphalin; Alphasterol; Anatola; Anatola A; Apexol; Apostavit; Aquasynth; Avibon; Avitol; Axerol; Axerophthol; Bentavit A; Biosterol; Chocola A; Disatabs Tabs; Dofsol; Dohyfral A; Epiteliol; Lard Factor; Myvpack; Oleovitamin A; Ophthalamin; Plivit A; Prepalin; Testavol; Vaflol; Veroftal; Vi-Alpha; Vitamin A; Vitamin A alcohol; Vitamin A1; Vitpex; Vogan-Neu; all-trans-Retinol; all-trans-Retinyl alcohol; all-trans-Vitamin A alcohol; retinol; trans-retinol; 68-26-8; Aoral; Atars; Vafol; A-Mulsal; A-Vitan; Vogan
Indication Vitamin deficiency [ICD11: 5B55] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 286.5 Topological Polar Surface Area 20.2
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
445354
PubChem SID
3756 ; 416404 ; 603541 ; 821173 ; 824333 ; 826984 ; 838308 ; 842011 ; 3138738 ; 7890334 ; 8144182 ; 8149779 ; 10299682 ; 10532643 ; 11528329 ; 11537746 ; 12146301 ; 14714468 ; 14799924 ; 17389530 ; 24697570 ; 24890099 ; 24890100 ; 24899395 ; 26612235 ; 26680020 ; 26709666 ; 26710635 ; 26747393 ; 26747394 ; 26753109 ; 26753110 ; 36888084 ; 46393062 ; 46508191 ; 47193665 ; 47193688 ; 47208199 ; 47217041 ; 47217042 ; 47291361 ; 47440523 ; 48416515 ; 48422815 ; 48425698 ; 48484015 ; 50105638 ; 53788786 ; 56374000 ; 57404676
ChEBI ID
ChEBI:17336
CAS Number
11103-57-4
TTD Drug ID
D0S7WX
Formula
C20H30O
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
InChI
1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChIKey
FPIPGXGPPPQFEQ-OVSJKPMPSA-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
4-hydroxyretinoic acid DM002374
6438629
Oxidation - 4-hydroxylation 1 [2]
4-Oxoretinoic acid DM002377
6437063
Unclear 1 [2]
5,6-epoxy-RA DM002376
5363137
Unclear 1 [2]
All-trans-18-Hydroxyretinoic acid DM002375
6506224
Oxidation - Hydrolyzationn 1 [2] , [3]
Retinoyl glucuronide DM002378
5281877
Conjugation - Glucuronidation 1 [2]
Retinyl beta-glucuronide DM002379
6440956
Conjugation - Glucuronidation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006380 NSC-122758 4-Hydroxyretinoic acid Oxidation - 4-hydroxylation CYP26C1 ... [2]
MR006381 NSC-122758 All-trans-18-Hydroxyretinoic acid Oxidation - Hydrolyzationn CYP26C1 ... [2], [3]
MR006382 NSC-122758 5,6-Epoxyretinoic acid Unclear CYP4A11 ... [2]
MR006383 NSC-122758 4-Oxoretinoic acid Unclear CYP3A7 ... [2]
MR006384 NSC-122758 Retinoyl b-glucuronide Conjugation - Glucuronidation Unclear [2]
MR006385 NSC-122758 Retinyl beta-glucuronide Conjugation - Glucuronidation Unclear [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[5]
Cytochrome P450 26C1 (CYP26C1) DME0600 Homo sapiens
CP26C_HUMAN
1.14.11.1
[2] , [3]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[6]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[7]
Cytochrome P450 2S1 (CYP2S1) DME0033 Homo sapiens
CP2S1_HUMAN
1.14.14.1
[8]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[9]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2] , [3]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[2]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[2] , [3]
Retinal dehydrogenase 2 (ALDH1A2) DME0287 Homo sapiens
AL1A2_HUMAN
1.2.1.36
[10]
Retinoic acid 4-hydroxylase 26A1 (CYP26A1) DME0227 Homo sapiens
CP26A_HUMAN
1.14.13.-
[11]
Retinol dehydrogenase 5 (RDH5) DME0583 Homo sapiens
RDH5_HUMAN
1.1.1.315
[12]
Short-chain dehydrogenase/reductase retSDR8 (DHRS9) DME0586 Homo sapiens
DHRS9_HUMAN
1.1.1.53
[10]
⏷ Show the Full List of 22  DME(s)
References
1 ClinicalTrials.gov (NCT00114868) Vitamin A Supplementation in Newborns Study.
2 Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8.
3 CYP26C1 is a hydroxylase of multiple active retinoids and interacts with cellular retinoic acid binding proteins. Mol Pharmacol. 2018 May;93(5):489-503.
4 Carotenoids as regulators for inter-species difference in cytochrome P450 1A expression and activity in ungulates and rats. Food Chem Toxicol. 2010 Nov;48(11):3201-8.
5 Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7.
6 Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human cytochrome P450 enzymes. Xenobiotica. 1999 Mar;29(3):231-41.
7 The role of inflammatory cells and cytochrome P450 in the potentiation of CCl4-induced liver injury by a single dose of retinol. Toxicol Appl Pharmacol. 1996 Dec;141(2):507-19.
8 The involvement of cytochrome p450 (CYP) 26 in the retinoic acid metabolism of human epidermal keratinocytes. Biochim Biophys Acta. 2009 Mar;1791(3):220-8.
9 Biosynthesis of all-trans-retinoic acid from all-trans-retinol: catalysis of all-trans-retinol oxidation by human P-450 cytochromes. Drug Metab Dispos. 2000 Mar;28(3):315-22.
10 Vitamin A metabolism by dendritic cells triggers an antimicrobial response against Mycobacterium tuberculosis. mSphere. 2019 Jun 5;4(3). pii: e00327-19.
11 Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41.
12 Generation of retinaldehyde for retinoic acid biosynthesis. Biomolecules. 2019 Dec 18;10(1). pii: E5.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.