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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015567
Secondary Accession Numbers
  • HMDB15567
Metabolite Identification
Common NameCalcipotriol
DescriptionCalcipotriol is only found in individuals that have used or taken this drug. It is a synthetic derivative of calcitriol or Vitamin D.The precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (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. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
Structure
Data?1582753311
Synonyms
ValueSource
CalcipotrieneChEBI
DaivonexChEBI
DovonexChEBI
Bristol-myers squibb brand OF calcipotrieneHMDB
PsorcutanHMDB
1,24(OH)2-22-Ene-24-cyclopropyl D3HMDB
Leo brand OF calcipotrieneHMDB
Schering brand OF calcipotrieneHMDB
CSL Brand OF calcipotrieneHMDB
Senosiain brand OF calcipotrieneHMDB
SoriluxHMDB
Farmacusi brand OF calcipotrieneHMDB
Heximar win careHMDB
(22E)-(24S)-1a,24-Dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1a,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriolHMDB
(22E)-(24S)-1Α,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1α,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriolHMDB
EnstilarHMDB
CalcipotriolKEGG
Chemical FormulaC27H40O3
Average Molecular Weight412.6047
Monoisotopic Molecular Weight412.297745146
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Namecalcipotriol
CAS Registry Number112965-21-6
SMILES
O[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC1
InChI Identifier
InChI=1S/C27H40O3/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/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
InChI KeyLWQQLNNNIPYSNX-UROSTWAQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.63ALOGPS
logP3.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.45 m³·mol⁻¹ChemAxon
Polarizability49.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.52431661259
DarkChem[M-H]-195.81731661259
DeepCCS[M-2H]-237.53130932474
DeepCCS[M+Na]+211.58630932474
AllCCS[M+H]+209.932859911
AllCCS[M+H-H2O]+207.632859911
AllCCS[M+NH4]+212.132859911
AllCCS[M+Na]+212.732859911
AllCCS[M-H]-206.332859911
AllCCS[M+Na-2H]-208.032859911
AllCCS[M+HCOO]-210.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CalcipotriolO[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC14099.5Standard polar33892256
CalcipotriolO[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC13392.3Standard non polar33892256
CalcipotriolO[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC13776.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Calcipotriol,1TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O3575.0Semi standard non polar33892256
Calcipotriol,1TMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O3558.0Semi standard non polar33892256
Calcipotriol,1TMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C3568.1Semi standard non polar33892256
Calcipotriol,2TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O3507.0Semi standard non polar33892256
Calcipotriol,2TMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C3504.2Semi standard non polar33892256
Calcipotriol,2TMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3487.0Semi standard non polar33892256
Calcipotriol,3TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3439.5Semi standard non polar33892256
Calcipotriol,1TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O3806.0Semi standard non polar33892256
Calcipotriol,1TBDMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O3776.8Semi standard non polar33892256
Calcipotriol,1TBDMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C3773.9Semi standard non polar33892256
Calcipotriol,2TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O3960.1Semi standard non polar33892256
Calcipotriol,2TBDMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C3933.4Semi standard non polar33892256
Calcipotriol,2TBDMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3922.1Semi standard non polar33892256
Calcipotriol,3TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)/C=C/[C@@H](O[Si](C)(C)C(C)(C)C)C2CC2)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C4073.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calcipotriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-2019000000-25fe74385dfaaadc4f642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcipotriol GC-MS (3 TMS) - 70eV, Positivesplash10-03di-2200159000-60ddca8d21526e4244de2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcipotriol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 10V, Positive-QTOFsplash10-002b-0019100000-dd8b67e911e2c011a4512016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 20V, Positive-QTOFsplash10-00fr-3349000000-721114fcaf3ed169df5d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 40V, Positive-QTOFsplash10-0fki-9568000000-c7e61ad61191fce88abe2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 10V, Negative-QTOFsplash10-03di-0006900000-01ce5bd91cb0ca4dcbec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 20V, Negative-QTOFsplash10-01ox-2009300000-7f4afaeab87ae0e61d8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 40V, Negative-QTOFsplash10-0006-9005000000-075615c00f3c0728d5ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 10V, Positive-QTOFsplash10-06tb-0139300000-4a9257a0b1cf140f5b7a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 20V, Positive-QTOFsplash10-0cki-1269200000-926c7873d1b6b3d9d1442021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 40V, Positive-QTOFsplash10-000b-2494000000-3044d26933d8919ecbfb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 10V, Negative-QTOFsplash10-03di-0002900000-6b048e3e028e205ac5982021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 20V, Negative-QTOFsplash10-03di-1505900000-d9fa5fd00776cc0e0e282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcipotriol 40V, Negative-QTOFsplash10-0a4i-0101900000-12080aba78c8a692b2ab2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB02300 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB02300 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02300
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4450880
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCalcipotriol
METLIN IDNot Available
PubChem Compound5288783
PDB IDMC9
ChEBI ID50749
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
References
  1. Sato H, Ogino Y, Takagi H, Hata J, Asano S, Ohta T, Komoriya K: Pharmacological profiles of high-concentration (20 microg/g) tacalcitol ointment: effects on cutaneous inflammation, epidermal proliferation, and differentiation in mice. J Dermatol. 2003 Jul;30(7):510-24. [PubMed:12928540 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Regulates transcription of hormone sensitive genes via its association with the WINAC complex, a chromatin-remodeling complex. Recruited to promoters via its interaction with the WINAC complex subunit BAZ1B/WSTF, which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis
Gene Name:
VDR
Uniprot ID:
P11473
Molecular weight:
48288.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can perform up to 6 rounds of hydroxylation of calcitriol leading to calcitroic acid. It also shows 23-hydroxylating activity leading to 1-alpha,25-dihydroxyvitamin D(3)-26,23-lactone as end product.
Gene Name:
CYP24A1
Uniprot ID:
Q07973
Molecular weight:
58874.695
References
  1. Jones G, Byford V, West S, Masuda S, Ibrahim G, Kaufmann M, Knutson JC, Strugnell S, Mehta R: Hepatic activation and inactivation of clinically-relevant vitamin D analogs and prodrugs. Anticancer Res. 2006 Jul-Aug;26(4A):2589-95. [PubMed:16886668 ]