(1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate

• ChemBase ID: 154550
• Molecular Formular: C27H42O4
• Molecular Mass: 430.61998
• Monoisotopic Mass: 430.30830982
• SMILES: C[C@H](C=C[C@H](C1CC1)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](C[C@@H](C1=C)O)O)C.O
• Canonical SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C/C=C/2\CCC[C@]3([C@H]2CC[C@@H]3[C@@H](C=C[C@H](C2CC2)O)C)C)/C1.O
• InChI: InChI=1S/C27H40O3.H2O/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2;/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3;1H2/t17-,22-,23-,24+,25-,26+,27-;/m1./s1
• InChIKey: XBKHACNRWFKJNC-XYGBQYPUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate
• IUPAC Traditional name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate
• Synonyms: (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; Calcipotriene; Calcipotriol hydrate

Database IDs

• CAS Number: 112965-21-6(anhydrous)
• MDL Number: MFCD10567086
• PubChem SID: 162248688
• PubChem CID: 71311896

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.8433506
• LogD (pH = 7.4): 3.8433506
• Log P: 3.843351
• Molar Refractivity: 125.4493 cm^3
• Polarizability: 48.449245 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥24 mg/mL
• Apperance: solid

Safety Information

• RTECS: VS2830000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H310-H315-H319-H335
• GHS Precautionary statements: P261-P280-P302 + P350-P305 + P351 + P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: room temp

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C27H40O3 · xH2O

DETAILS

Sigma Aldrich - C4369

Biochem/physiol Actions
Calcipotriol, a synthetic derivative of calcitriol or Vitamin D, is used in the treatment of psoriasis and marketed under the trade name Dovonex. It has comparable affinity with calcitriol (Vit. D) for the Vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. VDR belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. Binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation-related genes.