(1S,5S,6R,9S,20R)-5-hydroxy-20-methyl-6-(propan-2-yl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docos-15-ene-3,8,18,21-tetrone

• ChemBase ID: 129603
• Molecular Formular: C20H31N3O6S2
• Molecular Mass: 473.60664
• Monoisotopic Mass: 473.16542773
• SMILES: CC(C)[C@H]1NC(=O)[C@H]2CSSCC/C=C\[C@H](CC(=O)N[C@H](C)C(=O)N2)OC(=O)C[C@@H]1O
• Canonical SMILES: O=C1O[C@@H]2/C=C\CCSSC[C@H](C(=O)N[C@@H]([C@H](C1)O)C(C)C)NC(=O)[C@H](NC(=O)C2)C
• InChI: InChI=1S/C20H31N3O6S2/c1-11(2)18-15(24)9-17(26)29-13-6-4-5-7-30-31-10-14(20(28)23-18)22-19(27)12(3)21-16(25)8-13/h4,6,11-15,18,24H,5,7-10H2,1-3H3,(H,21,25)(H,22,27)(H,23,28)/t12-,13-,14-,15+,18-/m1/s1
• InChIKey: XFLBOEMFLGLWFF-ZURLZEQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,6R,9S,20R)-5-hydroxy-20-methyl-6-(propan-2-yl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docos-15-ene-3,8,18,21-tetrone
• IUPAC Traditional name: (1S,5S,6R,9S,20R)-5-hydroxy-6-isopropyl-20-methyl-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docos-15-ene-3,8,18,21-tetrone
• Synonyms: Spiruchostatin

Database IDs

• PubChem SID: 162223893
• PubChem CID: 60209141
• Wikipedia Title: Spiruchostatin

CALCULATED PROPERTIES

• Acid pKa: 10.836687
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.16099304
• LogD (pH = 7.4): -0.16113201
• Log P: -0.16099125
• Molar Refractivity: 120.2869 cm^3
• Polarizability: 47.164772 Å^3
• Polar Surface Area: 133.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true