(1R,9S,12R,13E,15S,16S,19R,20E,23S,25S,26R,27R,29R)-1,16-dihydroxy-12-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-25,27-dimethoxy-13,15,21,23,29-pentamethyl-19-(prop-2-en-1-yl)-11,30-dioxa-4-azatricyclo[24.3.1.04,9]triaconta-13,20-diene-2,3,10,18-tetrone

• ChemBase ID: 168990
• Molecular Formular: C44H69NO12
• Molecular Mass: 804.01816
• Monoisotopic Mass: 803.48197665
• SMILES: [C@@H]1([C@H](C[C@@H](CC1)[C@@H]1/C(=C/[C@@H]([C@H](CC(=O)[C@@H](/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@@H](C[C@H]([C@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)(O2)O)C)OC)OC)C)\C)CC=C)O)C)/C)OC)O
• Canonical SMILES: C=CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@@H](C[C@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@@H](/C(=C/[C@@H]([C@H](CC1=O)O)C)/C)[C@@H]1CC[C@H]([C@H](C1)OC)O)CCCC2
• InChI: InChI=1S/C44H69NO12/c1-10-13-30-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-29(6)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(31-15-16-33(46)36(23-31)53-7)28(5)21-27(4)34(47)24-35(30)48/h10,19,21,26-27,29-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,28-21+/t26-,27-,29+,30+,31+,32-,33+,34-,36-,37-,38+,39-,40?,44+/m0/s1
• InChIKey: CISNOWSTVWQKDD-XKYWYXTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12R,13E,15S,16S,19R,20E,23S,25S,26R,27R,29R)-1,16-dihydroxy-12-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-25,27-dimethoxy-13,15,21,23,29-pentamethyl-19-(prop-2-en-1-yl)-11,30-dioxa-4-azatricyclo[24.3.1.0^4,^9]triaconta-13,20-diene-2,3,10,18-tetrone
• IUPAC Traditional name: (1R,9S,12R,13E,15S,16S,19R,20E,23S,25S,26R,27R,29R)-1,16-dihydroxy-12-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-25,27-dimethoxy-13,15,21,23,29-pentamethyl-19-(prop-2-en-1-yl)-11,30-dioxa-4-azatricyclo[24.3.1.0^4,^9]triaconta-13,20-diene-2,3,10,18-tetrone
• Synonyms: [3R-[3R*(1R*,3R*,4R*),4E,6S*,7S*,10R*,11E,14S*,16S*,17R*,18S*,20R*,21R*,28aS*]]-7,8,10,13,14,15,16,17,18,19,20,21,26,27,28,28a-Hexadecahydro-7,21-dihydroxy-3-(4-hydroxy-3-methoxycyclohexyl)-16,18-dimethoxy-4,6,12,14,20-pentamethyl-10-(2-propenyl)-7,21-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclopentacosine-1,9,22,23(6H,25H)-tetrone; (E/Z)-FK-506 26,28-Allylic Ester Rearrangement Impurity

Database IDs

• CAS Number: 131944-48-4
• PubChem SID: 162263122
• PubChem CID: 71316761

CALCULATED PROPERTIES

• Acid pKa: 9.955601
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 5.630502
• LogD (pH = 7.4): 5.6293116
• Log P: 5.630517
• Molar Refractivity: 215.6421 cm^3
• Polarizability: 84.94902 Å^3
• Polar Surface Area: 178.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Pale Yellow Solid
• Melting Point: 115-120°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F370020

FK-506 (F370000) impurity. A new macrolite of thermal rearrangement of the immunosuppressant FK-506.

REFERENCES

• Ok, H., et al.: Tetrahedron Lett., et al.: 31, 6477 (1990)