Pimecrolimus
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,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
Molecular Identity
Pimecrolimus
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,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
PubChem CID: 6509979
Pimecrolimus is a lactam and a macrolide.
2D Structure
Properties
C43H68ClNO11
Molecular Formula
810.40
Molecular Weight
g/mol
809.4481
Exact Mass
Da
3.8
XLogP
Drug-like (Lipinski: < 5)
158
TPSA
May have limited oral absorption
2
H-Bond Donors
11
H-Bond Acceptors
1440
Complexity
SMILES
Canonical SMILES
SMILES: CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)Cl)C)O)C)OC)OC)C)CIsomeric SMILES
SMILES: CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\CSynonyms(20)
PimecrolimusElidel137071-32-0SDZ-ASM 981SDZ-ASM-981SDZ ASM 98133-epi-Chloro-33-desoxyascomycin(-)-PIMECROLIMUS7KYV510875D11AX1515,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 3-(2-(4-chloro-3-methoxycyclohexyl)-1-methylethenyl)-8-ethyl-, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S-(3R*(E(1S*,3S*,4R*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-DTXCID0026674PimecrolimusumRefChem:56730(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-12-((1E)-1-((1R,3R,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
Data from PubChem (NCBI)
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