(1R,8S,11S,12R,13S,16R,17E,20S,22S,23R,24R,26R)-1,13-dihydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-10,27-dioxa-3-azatricyclo[21.3.1.03,8]heptacos-17-ene-2,9,15-trione

• ChemBase ID: 175664
• 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]1[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@](O2)(O)C(=O)N2[C@H](C(=O)O1)CCCC2)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)N2[C@H](C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O)/C)CCCC2
• InChI: InChI=1S/C43H69NO11/c1-10-13-31-19-25(2)18-26(3)20-37(52-8)40-38(53-9)22-28(5)43(50,55-40)42(49)44-17-12-11-14-32(44)41(48)54-39(29(6)34(46)24-35(31)47)27(4)21-30-15-16-33(45)36(23-30)51-7/h10,19,21,26,28-34,36-40,45-46,50H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36-,37-,38+,39+,40?,43+/m0/s1
• InChIKey: RJOVJTTUBQJLEI-MLLPIJDJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,8S,11S,12R,13S,16R,17E,20S,22S,23R,24R,26R)-1,13-dihydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-10,27-dioxa-3-azatricyclo[21.3.1.0^3,^8]heptacos-17-ene-2,9,15-trione
• IUPAC Traditional name: (1R,8S,11S,12R,13S,16R,17E,20S,22S,23R,24R,26R)-1,13-dihydroxy-11-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-22,24-dimethoxy-12,18,20,26-tetramethyl-16-(prop-2-en-1-yl)-10,27-dioxa-3-azatricyclo[21.3.1.0^3,^8]heptacos-17-ene-2,9,15-trione
• Synonyms: [3S-[3R*[E(1S*,3S*,4S*)],4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,25aR*]]- 3,4,5,6,8,11,12,13,14,15,16,17,18,19,23,24,25,25a-Octadecahydro-5,19-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-15,19-epoxypyrido[2,1-c][1,4]oxaazacyclodocosine-1,7,20(22H)-trione; 9-Norketo FK-506

Database IDs

• CAS Number: 123719-19-7
• PubChem SID: 164231574
• PubChem CID: 71751219

CALCULATED PROPERTIES

• Acid pKa: 9.918648
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): 5.304884
• LogD (pH = 7.4): 5.3035884
• Log P: 5.3049006
• Molar Refractivity: 210.2743 cm^3
• Polarizability: 83.01034 Å^3
• Polar Surface Area: 161.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 101-105°C

Safety Information

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

DETAILS

Toronto Research Chemicals - N692080

FK-506 (F370000) impurity. A FK-506 derivative prepared via base-mediated FK-506 rearrangement and oxidation.

REFERENCES

• Askin, D., et al.: Tetrahedron Lett., 30, 671 (1989)