acetyl CoA   Click here for help

GtoPdb Ligand ID: 3038

Synonyms: acetyl coenzyme A | acetyl-CoA | acetylCoA | S-acetyl coenzyme A
PDB Ligand
Compound class: Metabolite
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 23
Hydrogen bond donors 9
Rotatable bonds 22
Topological polar surface area 418.36
Molecular weight 809.13
XLogP -6.07
No. Lipinski's rules broken 3
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Canonical SMILES O=C(NCCSC(=O)C)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
Isomeric SMILES O=C(NCCSC(=O)C)CCNC(=O)[C@@H](C(COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
InChI 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
1. Andrew Skaff D, Miziorko HM. (2010)
A visible wavelength spectrophotometric assay suitable for high-throughput screening of 3-hydroxy-3-methylglutaryl-CoA synthase.
Anal Biochem, 396 (1): 96-102. [PMID:19706283]
2. Haapalainen AM, Meriläinen G, Pirilä PL, Kondo N, Fukao T, Wierenga RK. (2007)
Crystallographic and kinetic studies of human mitochondrial acetoacetyl-CoA thiolase: the importance of potassium and chloride ions for its structure and function.
Biochemistry, 46 (14): 4305-21. [PMID:17371050]
3. Rokosz LL, Boulton DA, Butkiewicz EA, Sanyal G, Cueto MA, Lachance PA, Hermes JD. (1994)
Human cytoplasmic 3-hydroxy-3-methylglutaryl coenzyme A synthase: expression, purification, and characterization of recombinant wild-type and Cys129 mutant enzymes.
Arch Biochem Biophys, 312 (1): 1-13. [PMID:7913309]