disodium trihydrate (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3S)-3-{[2-({2-[(4-carboxy-3-hydroxy-3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl phosphate

• ChemBase ID: 133768
• Molecular Formular: C27H48N7Na2O23P3S
• Molecular Mass: 1009.668943
• Monoisotopic Mass: 1009.15305028
• SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)OP(=O)([O-])[O-])[C@@H](C(=O)NCCC(=O)NCCSC(=O)CC(C)(CC(=O)O)O)O.O.O.O.[Na+].[Na+]
• Canonical SMILES: O=C(NCCSC(=O)CC(CC(=O)O)(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.O.O.O.[Na+].[Na+]
• InChI: InChI=1S/C27H44N7O20P3S.2Na.3H2O/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34;;;;;/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45);;;3*1H2/q;2*+1;;;/p-2/t14-,19-,20-,21-,25-,27?;;;;;/m1...../s1
• InChIKey: YXPWBFOOMJTKME-MGMVQEOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium trihydrate (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3S)-3-{[2-({2-[(4-carboxy-3-hydroxy-3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl phosphate
• IUPAC Traditional name: disodium trihydrate (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3S)-3-{[2-({2-[(4-carboxy-3-hydroxy-3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl phosphate
• Synonyms: HMG-CoA; DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate

Database IDs

• CAS Number: 103476-21-7(anhydrous)
• PubChem SID: 24895729; 162228045
• PubChem CID: 71308712

CALCULATED PROPERTIES

• Acid pKa: 0.82053536
• H Acceptors: 20
• H Donor: 9
• LogD (pH = 5.5): -12.418398
• LogD (pH = 7.4): -15.735363
• Log P: -6.4497895
• Molar Refractivity: 191.4586 cm^3
• Polarizability: 77.15397 Å^3
• Polar Surface Area: 426.82 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥90% (HPLC)

DETAILS

Sigma Aldrich - H6132

Biochem/physiol Actions
DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is a substrate used to study the specificity and kinetics of the enzyme 3-hydroxyl-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase. HMG-CoA is the key intermediate in the biosynthsis of terpenes, cholesterol, and ketone bodies. Its metabolism is the target of statin drugs used to control cholesterol levels.