(1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-(prop-2-en-1-yl)tetradeca-1,9-dien-3-yl (2S)-1-formylpiperidine-2-carboxylate

• ChemBase ID: 169393
• Molecular Formular: C43H69NO11
• Molecular Mass: 776.00806
• Monoisotopic Mass: 775.48706203
• SMILES: [C@@H]1([C@H](C[C@@H](CC1)/C=C(/[C@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C[C@@H](C[C@@H]([C@@H]1[C@@H](CC(C(=O)O1)C)OC)OC)C)\C)CC=C)O)C)OC(=O)[C@@H]1CCCCN1C=O)\C)OC)O
• Canonical SMILES: C=CC[C@@H](C(=O)C[C@@H]([C@H]([C@@H](/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O)/C)OC(=O)[C@@H]1CCCCN1C=O)C)O)/C=C(/C[C@@H](C[C@@H]([C@H]1OC(=O)C(C[C@H]1OC)C)OC)C)\C
• InChI: InChI=1S/C43H69NO11/c1-10-13-32(19-26(2)18-27(3)20-38(52-8)41-39(53-9)22-29(5)42(49)55-41)36(48)24-35(47)30(6)40(54-43(50)33-14-11-12-17-44(33)25-45)28(4)21-31-15-16-34(46)37(23-31)51-7/h10,19,21,25,27,29-35,37-41,46-47H,1,11-18,20,22-24H2,2-9H3/b26-19+,28-21+/t27-,29?,30+,31-,32+,33-,34+,35-,37-,38-,39+,40+,41+/m0/s1
• InChIKey: LUBLZMAEBCCRLW-HLFIBTLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-(prop-2-en-1-yl)tetradeca-1,9-dien-3-yl (2S)-1-formylpiperidine-2-carboxylate
• IUPAC Traditional name: (1E,3S,4R,5S,8R,9E,12S,14S)-5-hydroxy-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-14-methoxy-14-[(2R,3R)-3-methoxy-5-methyl-6-oxooxan-2-yl]-2,4,10,12-tetramethyl-7-oxo-8-(prop-2-en-1-yl)tetradeca-1,9-dien-3-yl (2S)-1-formylpiperidine-2-carboxylate
• Synonyms: (2S)-1-Formyl-2-piperidinecarboxylic Acid (1S,2R,3S,6R,7E,10S,12S)-3-Hydroxy-1-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-12-methoxy-2,8,10-trimethyl-5-oxo-6-(2-propen-1-yl)-12-[(2R,3S,5RS)-tetrahydro-3-methoxy-5-methyl-6-oxo-2H-pyran-2-yl]-7-dodecen-1-yl Ester; 7-Formyl-10-keto Nor-8,9-keto 11-(RS)-FK-506DISCONTINUED

Database IDs

• PubChem SID: 162263525
• PubChem CID: 71316944

CALCULATED PROPERTIES

• Acid pKa: 14.071382
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 5.2919793
• LogD (pH = 7.4): 5.29198
• Log P: 5.29198
• Molar Refractivity: 210.8575 cm^3
• Polarizability: 83.18784 Å^3
• Polar Surface Area: 158.13 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F700545

FK-506 (F370000) impurity.

REFERENCES

• Bulusu, M.A.R. C., et al.: Tetrahedron Lett., 45, 2523 (2004)