Showing metabocard for Calcitriol (BMDB0001903)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:51 UTC
Update Date2020-06-04 18:58:59 UTC
MCDB ID BMDB0001903
Secondary Accession Numbers
  • BMDB01903
Metabolite Identification
Common NameCalcitriol
DescriptionCalcitriol, also known as 1a,25(OH)2D3 or calcitriol-nefro, 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. Thus, calcitriol is considered to be a secosteroid lipid molecule. Calcitriol is a drug which is used to treat vitamin d deficiency or insufficiency, refractory rickets (vitamin d resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis. Calcitriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Calcitriol is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1alpha,3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolChEBI
(1S,3R,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triolChEBI
(5Z,7E)-(1S,3R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolChEBI
1,25-DHCCChEBI
1-alpha-25-Dihydroxyvitamin D3ChEBI
1alpha,25(OH)2D3ChEBI
1alpha,25-DihydroxycholecalciferolChEBI
1alpha,25-Dihydroxyvitamin D3ChEBI
5-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diolChEBI
CalcijexChEBI
CalcitriolumChEBI
DecostriolChEBI
RocaltrolChEBI
(1S,3R,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-1,3,25-triolKegg
(1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triolGenerator
(1Α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triolGenerator
1-a-25-Dihydroxyvitamin D3Generator
1-Α-25-dihydroxyvitamin D3Generator
1a,25(OH)2D3Generator
1Α,25(OH)2D3Generator
1a,25-DihydroxycholecalciferolGenerator
1Α,25-dihydroxycholecalciferolGenerator
1a,25-Dihydroxyvitamin D3Generator
1Α,25-dihydroxyvitamin D3Generator
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriolHMDB
1,25 DihydroxycholecalciferolHMDB
1,25-DihydroxycholecalciferolHMDB
1,25-Dihydroxyvitamin DHMDB
1,25-Dihydroxyvitamin D3HMDB
1-alpha,25-Dihydroxyvitamin D3HMDB
1a,25-(OH)2D3HMDB
25-DihydroxycholecalciferolHMDB
Dihydroxyvitamin D3HMDB
Ro 21-5535HMDB
SilkisHMDB
SoltriolHMDB
TopitriolHMDB
ToptriolHMDB
1 alpha, 25-Dihydroxy-20-epi-vitamin D3HMDB
1 alpha,25-DihydroxycholecalciferolHMDB
1,25(OH)2-20EPi-D3HMDB
BocatriolHMDB
Calcitriol alphapharm brandHMDB
Calcitriol kyramedHMDB
Calcitriol-nefroHMDB
Hoffmann-la roche brand OF calcitriolHMDB
KyraMed, calcitriolHMDB
TirocalHMDB
alpha,25-Dihydroxyvitamin D3, 1HMDB
1,25-Dihydroxy-20-epi-vitamin D3HMDB
20 Epi 1alpha,25 dihydroxycholecaliferolHMDB
Abbott brand OF calcitriolHMDB
Calcitriol galderma brandHMDB
Calcitriol jenapharm brandHMDB
Calcitriol leo brandHMDB
Cryopharma brand OF calcitriolHMDB
Medice brand OF calcitriolHMDB
RenatriolHMDB
Roche brand OF calcitriolHMDB
1 alpha,25 DihydroxycholecalciferolHMDB
1 alpha,25-Dihydroxyvitamin D3HMDB
20-Epi-1alpha,25-dihydroxycholecaliferolHMDB
Calcitriol gry brandHMDB
Calcitriol kyramed brandHMDB
Calcitriol medice brandHMDB
Calcitriol nefroHMDB
Calcitriol renacare brandHMDB
Calcitriol roche brandHMDB
D3, 1,25-DihydroxyvitaminHMDB
D3, 1,25-Dihydroxy-20-epi-vitaminHMDB
Galderma brand OF calcitriolHMDB
Hoffmann la roche brand OF calcitriolHMDB
KyraMed brand OF calcitriolHMDB
Leo brand OF calcitriolHMDB
RenaCare brand OF calcitriolHMDB
SitriolHMDB
1 alpha, 25 Dihydroxy 20 epi vitamin D3HMDB
1 alpha,25 Dihydroxyvitamin D3HMDB
1,25 Dihydroxyvitamin D3HMDB
1,25 Dihydroxy 20 epi vitamin D3HMDB
Alphapharm brand OF calcitriolHMDB
Calcitriol abbott brandHMDB
Calcitriol cryopharma brandHMDB
CalcitriolNefroHMDB
D3, 1 alpha,25-DihydroxyvitaminHMDB
Gry brand OF calcitriolHMDB
Jenapharm brand OF calcitriolHMDB
OsteotriolHMDB
1a,25-Dihydroxyvitamin D3 / 1a,25-dihydroxycholecalciferol / calcitriolHMDB
1Α,25-dihydroxyvitamin D3 / 1α,25-dihydroxycholecalciferol / calcitriolHMDB
CalcitriolMeSH
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Namecalcitriol
CAS Registry Number32222-06-3
SMILES
C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C
InChI Identifier
InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChI KeyGMRQFYUYWCNGIN-NKMMMXOESA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.51ALOGPS
logP4.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.53 m³·mol⁻¹ChemAxon
Polarizability51.02 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aba-2019200000-f91cfe8e2e00e1a8f6da2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-2200139000-8f9b07740968867d2e472017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009100000-5d85e3fe2656c4f2c7982016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0239000000-16579742f7806ac7c5802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-3297000000-1ded6f55cc278e5facb82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0006900000-58dff5fdfef8e2a6c7c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0009300000-93004eb4d3b2dee27fe82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1119000000-a3201818a6bc9ce6cac42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0119000000-f58eb6212ebcce40560e2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-4396100000-7177c9113a57f65c8c662021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w1-1961000000-2ac1cc3761902eada6c42021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0505900000-160a8d14ac12dfdfe86e2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02k9-0839500000-5c13b18b5994b1b652882021-09-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00001 +/- 0.00001 uM details
HMDB IDHMDB0001903
DrugBank IDDB00136
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021822
KNApSAcK IDNot Available
Chemspider ID4444108
KEGG Compound IDC01673
BioCyc IDCALCITRIOL
BiGG ID2289241
Wikipedia LinkCalcitriol
METLIN ID6382
PubChem Compound5280453
PDB IDNot Available
ChEBI ID17823
References
Synthesis ReferenceChen, Yang-sheng; Zhai, Cui-yun; Ren, Li. Synthesis of calcitriol. Zhongguo Xinyao Zazhi (2005), 14(1), 69-72.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240. [PubMed:6788913 ]