(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-[(3-13C,3,3-2H2)prop-2-en-1-yl]-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

• ChemBase ID: 168989
• Molecular Formular: C44H69NO12
• Molecular Mass: 805.01081484
• Monoisotopic Mass: 804.48533149
• 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@](C(=O)C(=O)N3[C@H](C(=O)O1)CCCC3)(O2)O)C)OC)OC)C)\C)CC=[13CH2])O)C)\C)OC)O
• Canonical SMILES: [13CH2]=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@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@H](C1)OC)O)/C)CCCC2
• 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)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,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?,44+/m0/s1/i1+1
• InChIKey: QJJXYPPXXYFBGM-RUXCEBBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-[(3-^1^3C,3,3-^2H₂)prop-2-en-1-yl]-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-ene-2,3,10,16-tetrone
• IUPAC Traditional name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3S,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-[(3-^1^3C,3,3-^2H₂)prop-2-en-1-yl]-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-ene-2,3,10,16-tetrone
• Synonyms: Advagraf-13C,D2; FR 900506-13C,D2; Fujimycin-13C,D2; L 679934-13C,D2; Prograf-13C,D2; Protopic-13C,D2; TacroBell-13C,D2; Tacrolimus-13C,D2; Tsukubaenolide-13C,D2; FK-506-13C,D2 (Major)

Database IDs

• PubChem SID: 162263121
• PubChem CID: 71316760

CALCULATED PROPERTIES

• Acid pKa: 9.955601
• 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: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 90-92°C

Safety Information

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

DETAILS

Toronto Research Chemicals - F370002

A labelled immunosuppressant that blocks T cell proliferation in vitro by inhibiting the generation of several lymphokines, especially IL-2. Shown to inhibit the activity of FK-506 binding protein, thereby reversing its effects on sarcoplasmic reticulum

REFERENCES

• Asano, K., et al.: In Vivo, 10, 537 (1996)
• McCall, E., et al.: Circ. Res., 79, 1110 (1996)
• Raufman, J.P., et al.: J. Biol. Chem., 271, 19877 (1996)
• Rokaw, M.D., et al.: Am. J. Physiol., 271, C194 (1996)
• Knoll, G.A., et al.: Brit. Med. J., 318, 1104 (1