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

General Information of Drug (ID: DR2037)
Drug Name
Acetyl-CoA
Synonyms
Acetyl CoA; Coenzyme A, S-acetate; S-Acetyl coenzyme A; S-Acetylcoenzyme A; S-acetyl-CoA; S-acetyl-coenzyme A; acetyl coenzyme-A; acetyl-CoA; acetyl-S-CoA; acetylCoA; acetylcoenzyme-A; 3'-phosphoadenosine 5'-(3-{(3R)-4-[(3-{[2-(acetylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate); ACETYL COENZYME A; 72-89-9; 76Q83YLO3O; AcCoA; UNII-76Q83YLO3O; ac-CoA; ac-S-CoA
Indication Discovery agent Investigative [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 809.6 Topological Polar Surface Area 389
Heavy Atom Count 51 Rotatable Bond Count 20
Hydrogen Bond Donor Count 9 Hydrogen Bond Acceptor Count 22
Cross-matching ID
PubChem CID
444493
PubChem SID
1779 ; 3326 ; 585640 ; 820704 ; 822294 ; 823218 ; 824919 ; 826846 ; 829086 ; 829103 ; 829806 ; 831238 ; 831240 ; 834102 ; 837311 ; 841347 ; 855085 ; 7885691 ; 8027383 ; 8028055 ; 8028566 ; 10299538 ; 10317655 ; 10318175 ; 10318247 ; 10318521 ; 11110405 ; 11110459 ; 14710306 ; 14710334 ; 14710480 ; 17404244 ; 17422545 ; 17424997 ; 24277059 ; 24277587 ; 24424435 ; 24424471 ; 24778751 ; 24778980 ; 26703508 ; 26708546 ; 26716778 ; 26718485 ; 26718888 ; 29196119 ; 29211946 ; 36887496 ; 49742999 ; 50126532
ChEBI ID
CHEBI:15351
CAS Number
72-89-9
TTD Drug ID
D01AWE
Formula
C23H38N7O17P3S
Canonical SMILES
CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
InChI
1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
InChIKey
ZSLZBFCDCINBPY-ZSJPKINUSA-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
Acetoacetyl-CoA DM001687
92153
Oxidation - Beta Oxidation 1 [3] , [4]
HMG-CoA DM001688
445127
Unclear - Unclear 2 [5] , [4]
Malonyl CoA DM001692
644066
Unclear - Unclear 2 [5] , [6] , [7]
Acetoacetate DM001690
6971017
Unclear - Unclear 3 [5] , [4] , [8]
Malonyl semialdehyde DM019946
440865
Unclear - Unclear 3 [5] , [9] , [10]
Mevalonate DM003097
5288798
Unclear - Unclear 3 [5] , [9]
Triacylglycero DM001693
11146
Unclear - Unclear 3 [5]
3-hydroxypropionic acid DM019947
68152
Unclear - Unclear 4 [6]
Beta-hydroxybutyrate DM001691 N. A. Unclear - Unclear 4 [5] , [4] , [8]
CHOL DM001689
5997
Unclear - Unclear 4 [5] , [9] , [10]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002976 Acetyl-CoA Acetoacetyl-CoA Oxidation - Beta Oxidation Unclear [3], [4]
MR002977 Acetoacetyl-CoA HMG-CoA Unclear - Unclear Unclear [5], [4]
MR002982 Acetoacetyl-CoA Malonyl-CoA Unclear - Unclear Unclear [5], [6], [7]
MR002978 HMG-CoA Mevalonate Unclear - Unclear Unclear [5], [9]
MR002980 HMG-CoA Acetoacetate Unclear - Unclear Unclear [5], [4], [8]
MR002983 Malonyl-CoA Malonyl semialdehyde Unclear - Unclear Unclear [5], [9], [10]
MR002985 Malonyl-CoA Triacylglycero Unclear - Unclear Unclear [5]
MR002981 Acetoacetate Beta-hydroxybutyrate Unclear - Unclear Unclear [5], [4], [8]
MR002984 Malonyl semialdehyde 3-hydroxypropionic acid Unclear - Unclear Unclear [6]
MR002979 Mevalonate Cholesterol Unclear - Unclear Unclear [5], [9], [10]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cysteinyl-conjugate N-acetyltransferase (NAT8) DME0336 Homo sapiens
NAT8_HUMAN
2.3.1.80
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cysteinyl-conjugate N-acetyltransferase (NAT8) DME0336 Km = 0.023 microM
NAT8_HUMAN
[2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 3038).
2 Molecular identification of NAT8 as the enzyme that acetylates cysteine S-conjugates to mercapturic acids. J Biol Chem. 2010 Jun 11;285(24):18888-98.
3 U. S. FDA Label -Acetyl-CoA
4 Activation of G protein-coupled receptors by ketone bodies: Clinical implication of the ketogenic diet in metabolic disorders. Front Endocrinol (Lausanne). 2022 Oct 20;13:972890. doi: 10.3389/fendo.2022.972890.
5 Compartmentalised acyl-CoA metabolism and roles in chromatin regulation Mol Metab. 2020 Aug;38:100941. doi: 10.1016/j.molmet.2020.01.005.
6 High throughput (13)C-metabolic flux analysis of 3-hydroxypropionic acid producing Pichia pastoris reveals limited availability of acetyl-CoA and ATP due to tight control of the glycolytic flux. Microb Cell Fact. 2023 Jun 29;22(1):117. doi: 10.1186/s12934-023-02123-0.
7 Acetyl-CoA carboxylase 1 is a suppressor of the adipocyte thermogenic program. Cell Rep. 2023 May 30;42(5):112488. doi: 10.1016/j.celrep.2023.112488.
8 In Vivo Estimation of Ketogenesis Using Metabolic Flux Analysis-Technical Aspects and Model Interpretation. Metabolites. 2021 Apr 28;11(5):279. doi: 10.3390/metabo11050279.
9 Early hyperlipidemia triggers metabolomic reprogramming with increased SAH, increased acetyl-CoA-cholesterol synthesis, and decreased glycolysis. Redox Biol. 2023 Jun 16;64:102771. doi: 10.1016/j.redox.2023.102771.
10 (2)H,(13)C-Cholesterol for Dynamics and Structural Studies of Biological Membranes. ACS Omega. 2022 May 10;7(20):17151-17160. doi: 10.1021/acsomega.2c00796.

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