Calcipotriol
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
Molecular Identity
Calcipotriol
trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
PubChem CID: 5288783
Calcipotriol is a seco-cholestane that is 26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene carrying additional hydroxy substituents at positions 1, 3 and 24. It is used (as its hydrate) in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. It has a role as an antipsoriatic and a drug allergen. It is a triol, a secondary alcohol, a seco-cholestane, a hydroxy seco-steroid and a member of cyclopropanes.
2D Structure
Properties
C27H40O3
Molecular Formula
412.60
Molecular Weight
g/mol
412.2977
Exact Mass
Da
4.3
XLogP
Drug-like (Lipinski: < 5)
60.7
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
3
H-Bond Acceptors
743
Complexity
SMILES
Canonical SMILES
SMILES: CC(C=CC(C1CC1)O)C2CCC3C2(CCCC3=CC=C4CC(CC(C4=C)O)O)CIsomeric SMILES
SMILES: C[C@H](/C=C/[C@H](C1CC1)O)[C@H]2CC[C@@H]\3[C@@]2(CCC/C3=C\C=C/4\C[C@H](C[C@@H](C4=C)O)O)CSynonyms(20)
Calcipotriolcalcipotriene112965-21-6DovonexCalciptriolDaivonexCalcitreneMC-903Calcipotriol anhydrousPRI-2201DTXSID0046648CHEBI:50749143NQ3779B(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diolMC903
Data from PubChem (NCBI)
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