(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-12-[(1E)-1-[(1R,3S,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-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: 176726
• Molecular Formular: C43H68ClNO11
• Molecular Mass: 810.45312
• Monoisotopic Mass: 809.44808968
• SMILES: [C@@H]12CCCCN1C(=O)C(=O)[C@]1([C@@H](C[C@H]([C@@H]([C@H](C[C@H](C/C(=C/[C@H](C(=O)C[C@@H]([C@H]([C@H](OC2=O)/C(=C/[C@@H]2CC[C@@H]([C@H](C2)OC)Cl)/C)C)O)CC)/C)C)OC)O1)OC)C)O
• 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)Cl)/C)CCCC2
• InChI: InChI=1S/C43H68ClNO11/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)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,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: KASDHRXLYQOAKZ-XOKIQWJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-12-[(1E)-1-[(1R,3S,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-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,17R,18E,21S,23S,24R,25R,27R)-12-[(1E)-1-[(1R,3S,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-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: 33-Epichloro-33-desoxyascomycin; 33-epi-Chloro-33-desoxyascomycin; ASM 981; Elidel; Picrolimus; SDZ-ASM 981; Pimecrolimus

Database IDs

• CAS Number: 137071-32-0
• PubChem SID: 164232636
• PubChem CID: 71751667

CALCULATED PROPERTIES

• Acid pKa: 9.955626
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 6.808116
• LogD (pH = 7.4): 6.806926
• Log P: 6.808131
• Molar Refractivity: 214.0262 cm^3
• Polarizability: 84.57097 Å^3
• Polar Surface Area: 158.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P445000

Macrolactam ascomycin derivative; inhibits production of pro-inflammatory cytokines by T cells and mast cells. Immunosuppresant.

REFERENCES

• Gassberger, M., et al.: Br. J. Dermatol., 141, 264 (1999)
• Queille-Roussel, C., et al.: Contact Dermatitis, 42, 349 (1999)