(1R,9S,12S,15R,16E,19S,21S,22R,23R,25R)-1-hydroxy-12-[(2S,3S,4E)-3-hydroxy-5-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-4-methylpent-4-en-2-yl]-21,23-dimethoxy-17,19,25-trimethyl-15-(prop-2-en-1-yl)-11,26-dioxa-4-azatricyclo[20.3.1.04,9]hexacos-16-ene-2,3,10,14-tetrone

• ChemBase ID: 171795
• Molecular Formular: C44H69NO12
• Molecular Mass: 804.01816
• Monoisotopic Mass: 803.48197665
• SMILES: [C@@H]1([C@H](C[C@@H](CC1)/C=C(/[C@H]([C@@H]([C@@H]1CC(=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)C)O)\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@](C(=O)C(=O)N3[C@H](C(=O)O[C@@H](CC1=O)[C@H]([C@@H](/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O)/C)O)C)CCCC3)(O)[C@@H](C[C@H]2OC)C
• InChI: InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-35(24-34(31)47)29(6)39(48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-33,35-40,46,48,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,35-,36-,37-,38+,39+,40?,44+/m0/s1
• InChIKey: YXGKFJMGANONSQ-DXXMAELFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,15R,16E,19S,21S,22R,23R,25R)-1-hydroxy-12-[(2S,3S,4E)-3-hydroxy-5-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-4-methylpent-4-en-2-yl]-21,23-dimethoxy-17,19,25-trimethyl-15-(prop-2-en-1-yl)-11,26-dioxa-4-azatricyclo[20.3.1.0^4,^9]hexacos-16-ene-2,3,10,14-tetrone
• IUPAC Traditional name: (1R,9S,12S,15R,16E,19S,21S,22R,23R,25R)-1-hydroxy-12-[(2S,3S,4E)-3-hydroxy-5-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-4-methylpent-4-en-2-yl]-21,23-dimethoxy-17,19,25-trimethyl-15-(prop-2-en-1-yl)-11,26-dioxa-4-azatricyclo[20.3.1.0^4,^9]hexacos-16-ene-2,3,10,14-tetrone
• Synonyms: [3S-[3R*[1R*,2R*,4(1S*,3S*,4S*)],6S*,10R*,12R*,13R*,14R*,16S*,17S*,24aR*]]-6,9,10,11,12,13,14,15,16,17,22,23,24,24a-tetradecahydro-17-hydroxy-3-[2-hydroxy-4-(4-hydroxy-3-methoxycyclohexyl)-1,3-dimethyl-3-butenyl]-12,14-dimethoxy-8,10,16-trimethyl-6-(2-propenyl)-13,17-epoxy-3H-pyrido[2,1-c][1,4]oxaazacycloheneicosine-1,5,18,19(4H,21H)-tetrone; Iso-FK-506 (iso-Tacrolimus)

Database IDs

• CAS Number: 134590-88-8
• PubChem SID: 164227705
• PubChem CID: 71749558

CALCULATED PROPERTIES

• Acid pKa: 9.955589
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 5.594105
• LogD (pH = 7.4): 5.5929146
• Log P: 5.59412
• Molar Refractivity: 215.6203 cm^3
• Polarizability: 84.94902 Å^3
• Polar Surface Area: 178.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 82-87°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I816250

An isomer of FK-506 (F370000) from fermentation of Streptomyces tsukubaensis, as immunosuppressant and antiinflammatory agent.

REFERENCES

• Grassberger, M.A., et al.: Tetrahedron, 48, 413 (1992)