{[(2R,3S,5R,7S,8R,9S)-2-[(1S,3S,4R,5R,6R,7E,9E,11E,13E)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxy}phosphonic acid

• ChemBase ID: 2573
• Molecular Formular: C50H81N4O15P
• Molecular Mass: 1009.169701
• Monoisotopic Mass: 1008.54360454
• SMILES: COC[C@@H]([C@H](O)[C@H](O)C(=O)NCC[C@H](C)c1nc(/C=C/C[C@@H]2O[C@]3(C[C@H](O)[C@H]2C)O[C@H]([C@H](C[C@H](O)[C@@H](C)[C@H](O)[C@H](C)/C=C(\C)/C(=C/C=C/C(=C/C#N)/C)/C)OC)[C@@H](OP(=O)(O)O)C3(C)C)co1)N(C)C
• Canonical SMILES: COC[C@@H]([C@@H]([C@@H](C(=O)NCC[C@@H](c1occ(n1)/C=C/C[C@@H]1O[C@]2(C[C@@H]([C@H]1C)O)O[C@@H]([C@H](C2(C)C)OP(=O)(O)O)[C@H](C[C@@H]([C@H]([C@@H]([C@@H](/C=C(/C(=C/C=C/C(=C/C#N)/C)/C)\C)C)O)C)O)OC)C)O)O)N(C)C
• InChI: InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20+,30-17+,32-24+/t31-,33+,34+,35+,37-,38-,39-,40-,41-,42+,43-,44-,45+,46+,50+/m0/s1
• InChIKey: FKAWLXNLHHIHLA-UWOGDOESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,5R,7S,8R,9S)-2-[(1S,3S,4R,5R,6R,7E,9E,11E,13E)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @calyculin A
• Synonyms: Calyculin A

Database IDs

• CAS Number: 101932-71-2
• PubChem SID: 160966023; 46506773
• PubChem CID: 46936510

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.1460295
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): 1.6894811
• LogD (pH = 7.4): 0.49908644
• Log P: 1.7695262
• Molar Refractivity: 267.0961 cm^3
• Polarizability: 103.73827 Å^3
• Polar Surface Area: 286.99 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.65
• LOG S: -3.61
• Solubility (Water): 2.49e-01 g/l

DETAILS

DrugBank - DB02860

Drug information: experimental