trisodium (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-[({hydroxy[(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl phosphonato)oxy]phosphoryl}oxy)methyl]oxolan-3-yl phosphate

• ChemBase ID: 133385
• Molecular Formular: C25H37N7Na3O18P3S
• Molecular Mass: 917.552973
• Monoisotopic Mass: 917.08217111
• SMILES: CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)OP(=O)([O-])[O-])O.[Na+].[Na+].[Na+]
• Canonical SMILES: O=C(NCCSC(=O)CC(=O)C)CCNC(=O)C(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.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C25H40N7O18P3S.3Na/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32;;;/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41);;;/q;3*+1/p-3/t14-,18-,19-,20?,24-;;;/m1.../s1
• InChIKey: KJJYKBIEKQJXHM-YRWRHZSKSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-[({hydroxy[(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl phosphonato)oxy]phosphoryl}oxy)methyl]oxolan-3-yl phosphate
• IUPAC Traditional name: trisodium (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl phosphonato)oxyphosphoryl]oxy}methyl)oxolan-3-yl phosphate
• Synonyms: Acetoacetyl-CoANa3; Acetoacetyl coenzyme A sodium salt hydrate; Acetoacetyl coenzyme A 钠盐 水合物

Database IDs

• CAS Number: 1420-36-6(freeacid)
• PubChem SID: 24890567; 162227662
• PubChem CID: 16218855

CALCULATED PROPERTIES

• Acid pKa: 0.8207477
• H Acceptors: 18
• H Donor: 6
• LogD (pH = 5.5): -10.3055315
• LogD (pH = 7.4): -11.922316
• Log P: -5.7028904
• Molar Refractivity: 178.7381 cm^3
• Polarizability: 72.16904 Å^3
• Polar Surface Area: 389.19 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless to faintly yellow

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC); ≥90%
• Impurities: ≤1% ATP (HPLC); ≤6% coenzyme A (HPLC); ≤8% coenzyme A oxidized (HPLC)
• Empirical Formula (Hill Notation): C25H40N7O18P3S · xNa+ · yH2O

DETAILS

Sigma Aldrich - A1625

Application
Substrate for acetoacetyl-CoA thiolase EC 2.3.1.9; Role in the biosynthesis of nonactin.
Acetoacetyl coenzyme A (Acetoacetyl-CoA) may be used as a substrate for a number of enzymes including; acetoacetyl-CoA thiolase (EC 2.3.1) which produces acetyl-CoA in reverse condensation reaction and (3-Hydroxy-3-methylglutaryl coenzyme A (CoA) synthase (HMGCS)) which produces 3-hydroxy-3-methylglutaryl (HMG)-CoA in the mevalonate pathway leading to terpenoid biosynthesis. Acetoacetyl-CoA is also a precursor of poly-beta-hydroxybutyrate polymers in microorganisms.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A1625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 00062

Application
Substrate for acetoacetyl-CoA thiolase EC 2.3.1.9; Role in the biosynthesis of nonactin.
Acetoacetyl coenzyme A (Acetoacetyl-CoA) may be used as a substrate for a number of enzymes including; acetoacetyl-CoA thiolase (EC 2.3.1) which produces acetyl-CoA in reverse condensation reaction and (3-Hydroxy-3-methylglutaryl coenzyme A (CoA) synthase (HMGCS)) which produces 3-hydroxy-3-methylglutaryl (HMG)-CoA in the mevalonate pathway leading to terpenoid biosynthesis. Acetoacetyl-CoA is also a precursor of poly-β-hydroxybutyrate polymers in microorganisms.
Other Notes
Substrate for acetoacetyl-CoA thiolase EC 2.3.1.91; Role in the biosynthesis of nonactin2