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

• ChemBase ID: 160832
• Molecular Formular: C43H69NO12
• Molecular Mass: 792.00746
• Monoisotopic Mass: 791.48197665
• SMILES: C1CCN2[C@@H](C1)C(=O)O[C@@H]([C@H]([C@H](CC(=O)[C@@H](/C=C(\C[C@H](C[C@@H]([C@H]1O[C@@](C(=O)C2=O)([C@@H](C[C@H]1OC)C)O)OC)C)/C)CC)O)C)/C(=C/[C@H]1CC[C@@H]([C@H](C1)OC)O)/C
• Canonical SMILES: 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/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18-,26-20+/t25-,27+,28+,29+,30-,31-,32-,33-,35-,36+,37+,38+,39?,43+/m0/s1
• InChIKey: ZDQSOHOQTUFQEM-WLWIDMSTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,13R,14S,17S,18Z,21S,23R,24R,25R,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1S,3S,4S)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-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,17S,18Z,21S,23R,24R,25R,27R)-17-ethyl-1,14-dihydroxy-12-[(1E)-1-[(1S,3S,4S)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^4,^9]octacos-18-ene-2,3,10,16-tetrone
• Synonyms: Changchuanmycin; Immunomycin; FK 520; FR 520; FR 900520; L 683590; Ascomycin

Database IDs

• CAS Number: 104987-12-4
• PubChem SID: 162254967
• PubChem CID: 71313500

CALCULATED PROPERTIES

• Acid pKa: 9.955601
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): 5.453524
• LogD (pH = 7.4): 5.452334
• Log P: 5.4535394
• Molar Refractivity: 210.9752 cm^3
• Polarizability: 83.36068 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 Solid
• Melting Point: 153-157°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A781000

A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases.

REFERENCES

• Matuszewski, B., et al.: Anal. Chem., 75, 3019 (2003)
• Taylor, P., et al.: Clin. Chem., 51, 1890(2003)