(1S,3S,7R,8R,8aS)-8-{2-[(2R,4S)-4-hydroxy-1-{[5-(hydroxymethyl)-6-methoxynaphthalen-2-yl]methyl}-6-oxopiperidin-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-methylbutanoate

• ChemBase ID: 3567
• Molecular Formular: C37H49NO6
• Molecular Mass: 603.78806
• Monoisotopic Mass: 603.35598829
• SMILES: CC[C@@H](C)C(=O)O[C@H]1C[C@H](C)C=C2C=C[C@@H](C)[C@@H](CC[C@@H]3C[C@H](O)CC(=O)N3Cc3ccc4c(ccc(OC)c4CO)c3)[C@H]12
• Canonical SMILES: CC[C@H](C(=O)O[C@H]1C[C@H](C)C=C2[C@@H]1[C@H](CC[C@@H]1C[C@H](O)CC(=O)N1Cc1ccc3c(c1)ccc(c3CO)OC)[C@@H](C=C2)C)C
• InChI: InChI=1S/C37H49NO6/c1-6-23(3)37(42)44-34-16-22(2)15-27-9-7-24(4)30(36(27)34)13-11-28-18-29(40)19-35(41)38(28)20-25-8-12-31-26(17-25)10-14-33(43-5)32(31)21-39/h7-10,12,14-15,17,22-24,28-30,34,36,39-40H,6,11,13,16,18-21H2,1-5H3/t22-,23-,24-,28-,29+,30-,34+,36-/m1/s1
• InChIKey: WPVRNXUYVXQXPY-UVJQNAMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7R,8R,8aS)-8-{2-[(2R,4S)-4-hydroxy-1-{[5-(hydroxymethyl)-6-methoxynaphthalen-2-yl]methyl}-6-oxopiperidin-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-methylbutanoate
• IUPAC Traditional name: (1S,3S,7R,8R,8aS)-8-{2-[(2R,4S)-4-hydroxy-1-{[5-(hydroxymethyl)-6-methoxynaphthalen-2-yl]methyl}-6-oxopiperidin-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-methylbutanoate
• Synonyms: LFA703

Database IDs

• PubChem SID: 46504607; 160967005
• PubChem CID: 46936832

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.61674
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.1856313
• LogD (pH = 7.4): 5.1856313
• Log P: 5.1856313
• Molar Refractivity: 174.3708 cm^3
• Polarizability: 68.76783 Å^3
• Polar Surface Area: 96.3 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.51
• LOG S: -5.6
• Solubility (Water): 1.52e-03 g/l

DETAILS

DrugBank - DB03932

Drug information: experimental