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

General Information of Drug (ID: DR2468)
Drug Name
Deoxycholic acid
Synonyms Deoxycholicacid; ATX-101, APIM Therapeutics; Proliferating cell nuclear antigen (peptide, cancer), APIM
Indication Obesity [ICD11: 5B81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 392.6 Topological Polar Surface Area 77.8
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
222528
PubChem SID
7102 ; 74413 ; 585592 ; 585594 ; 618558 ; 819839 ; 828927 ; 837869 ; 841387 ; 855438 ; 3135058 ; 7850928 ; 7887027 ; 7887240 ; 8138505 ; 9377073 ; 11446298 ; 14717701 ; 15953970 ; 24277530 ; 24858743 ; 24893692 ; 24893857 ; 25622261 ; 29204024 ; 30425733 ; 46391767 ; 47193711 ; 47959957 ; 50086825 ; 53777021 ; 53786947 ; 56311772 ; 57399984 ; 80526818 ; 85279390 ; 90451786 ; 93167216 ; 99444161 ; 99455580 ; 103578732 ; 113476161 ; 124807327 ; 124812927 ; 125011664 ; 125308743 ; 126523430 ; 126596873 ; 126606721 ; 127310875
ChEBI ID
CHEBI:28834
CAS Number
83-44-3
TTD Drug ID
D02PQB
Formula
C24H40O4
Canonical SMILES
CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
InChI
1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChIKey
KXGVEGMKQFWNSR-LLQZFEROSA-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
12-keto-DCA DM017042 N. A. Oxidation - 12-OH-dehydrogenation 1 [4]
15beta-hydroxy-DCA DM017038 N. A. Oxidation - 15-hydroxylation 1 [4]
1beta-OH-DCA DM017040 N. A. Unclear 1 [2]
3-keto-DCA DM017041 N. A. Oxidation - 3-OH-dehydrogenation 1 [4]
Cholic acid DM004937
221493
Oxidation - 7-hydroxylation 1 [4]
Taurocholic acid DM014903
6675
Unclear 1 [5]
UCA DM016252
67122255
Oxidation - 7-hydroxylation 1 [4]
15beta-hydroxy-12-oxo-DCA DM017039 N. A. Oxidation - 12-OH-dehydrogenation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013670 Deoxycholic acid 15beta-hydroxy-DCA Oxidation - 15-hydroxylation Unclear [4]
MR013672 Deoxycholic acid Taurocholic acid Unclear Unclear [5]
MR013673 Deoxycholic acid 1beta-OH-DCA Unclear CYP46A1 ... [2]
MR013674 Deoxycholic acid 3-keto-DCA Oxidation - 3-OH-dehydrogenation Unclear [4]
MR013675 Deoxycholic acid 12-keto-DCA Oxidation - 12-OH-dehydrogenation Unclear [4]
MR013676 Deoxycholic acid UCA Oxidation - 7-hydroxylation Unclear [4]
MR013677 Deoxycholic acid CA Oxidation - 7-hydroxylation Unclear [4]
MR013671 15beta-hydroxy-DCA 15beta-hydroxy-12-oxo-DCA Oxidation - 12-OH-dehydrogenation Unclear [4]
⏷ 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
Cholesterol 24-hydroxylase (CYP46A1) DME0028 Homo sapiens
CP46A_HUMAN
1.14.14.25
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [3]
References
1 Deoxycholic acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP3A Specifically Catalyzes 1-Hydroxylation of Deoxycholic Acid: Characterization and Enzymatic Synthesis of a Potential Novel Urinary Biomarker for CYP3A Activity
3 A biosynthetic pathway for a prominent class of microbiota-derived bile acids. Nat Chem Biol. 2015 Sep;11(9):685-90.
4 Deoxycholic acid transformations catalyzed by selected filamentous fungi
5 Increased sulfation and decreased 7alpha-hydroxylation of deoxycholic acid in ethinyl estradiol-induced cholestasis in rats

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