3-[(2-{3-[(2R)-3-[({[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-oxopropanoic acid

• ChemBase ID: 4095
• Molecular Formular: C24H38N7O19P3S
• Molecular Mass: 853.580303
• Monoisotopic Mass: 853.11560292
• SMILES: CC(C)(CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1OP(=O)(O)O)n1cnc2c1ncnc2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(=O)O
• Canonical SMILES: O=C(NCCSC(=O)CC(=O)O)CCNC(=O)[C@@H](C(CO[P@](=O)(O[P@@](=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/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17+,18-,19-,23+/m0/s1
• InChIKey: LTYOQGRJFJAKNA-IJCONWDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-{3-[(2R)-3-[({[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-oxopropanoic acid
• IUPAC Traditional name: @malonyl-coenzyme A
• Synonyms: Malonyl-Coenzyme A

Database IDs

• CAS Number: 524-14-1
• PubChem SID: 46506952; 160967528
• PubChem CID: 46936998

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.81318885
• H Acceptors: 19
• H Donor: 10
• LogD (pH = 5.5): -12.200845
• LogD (pH = 7.4): -15.443948
• Log P: -7.0881505
• Molar Refractivity: 178.5521 cm^3
• Polarizability: 71.2804 Å^3
• Polar Surface Area: 400.93 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.62
• LOG S: -2.35
• Solubility (Water): 3.80e+00 g/l

DETAILS

DrugBank - DB04524

• Drug Groups: experimental
• Description: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems. [PubChem]