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Record Information
Version3.6
Creation Date2006-03-10 10:07:06 UTC
Update Date2013-02-09 00:10:59 UTC
HMDB IDHMDB01903
Secondary Accession NumbersNone
Metabolite Identification
Common NameCalcitriol
DescriptionThe physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (calcifediol). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.--PubChem.
Structure
Thumb
Synonyms
  1. (3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriol
  2. 1,25 Dihydroxycholecalciferol
  3. 1,25-Dihydroxycholecalciferol
  4. 1,25-Dihydroxyvitamin D
  5. 1,25-Dihydroxyvitamin D3
  6. 1-alpha,25-Dihydroxyvitamin D3
  7. 1a,25-(OH)2D3
  8. 1a,25-Dihydroxycholecalciferol
  9. 1a,25-Dihydroxyvitamin D3
  10. 25-Dihydroxycholecalciferol
  11. Calcijex
  12. Calcitriol
  13. Dihydroxyvitamin D3
  14. Ro 21-5535
  15. Rocaltrol
  16. Silkis
  17. Soltriol
  18. Topitriol
  19. Toptriol
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)(O)C)[C@H]1CC[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
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassSesterterpenes
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Vitamin D and Derivatives
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Steroid
  • Tertiary Alcohol
Direct ParentSesterterpenes
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0067ALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.53 m3·mol-1ChemAxon
Polarizability51.52 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Medulla
  • Bladder
  • Fibroblasts
  • Gonads
  • Gut
  • Intestine
  • Kidney
  • Muscle
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000086 (0.000029-0.00016) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000074 (0.000052-0.000096) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021822
KNApSAcK IDNot Available
Chemspider ID4444108
KEGG Compound IDC01673
BioCyc IDCALCITRIOL
BiGG ID2289241
Wikipedia LinkCalcitriol
NuGOwiki LinkHMDB01903
Metagene LinkHMDB01903
METLIN ID6382
PubChem Compound5280453
PDB IDVDX
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. Mason RS, Lissner D, Grunstein HS, Posen S: A simplified assay for dihydroxylated vitamin D metabolites in human serum: application to hyper- and hypovitaminosis D. Clin Chem. 1980 Mar;26(3):444-50. Pubmed: 6892691
  2. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69. Pubmed: 227368
  3. Mason RS, Frankel T, Chan YL, Lissner D, Posen S: Vitamin D conversion by sarcoid lymph node homogenate. Ann Intern Med. 1984 Jan;100(1):59-61. Pubmed: 6546329
  4. Mallette LE: Case report: hypoparathyroidism with menses-associated hypocalcemia. Am J Med Sci. 1992 Jul;304(1):32-7. Pubmed: 1642251
  5. Ott SM, Chesnut CH 3rd: Calcitriol treatment is not effective in postmenopausal osteoporosis. Ann Intern Med. 1989 Feb 15;110(4):267-74. Pubmed: 2913914
  6. Bhan I, Shah A, Holmes J, Isakova T, Gutierrez O, Burnett SA, Juppner H, Wolf M: Post-transplant hypophosphatemia: Tertiary 'Hyper-Phosphatoninism'? Kidney Int. 2006 Oct;70(8):1486-94. Epub 2006 Aug 30. Pubmed: 16941023
  7. Josephson MA, Schumm LP, Chiu MY, Marshall C, Thistlethwaite JR, Sprague SM: Calcium and calcitriol prophylaxis attenuates posttransplant bone loss. Transplantation. 2004 Oct 27;78(8):1233-6. Pubmed: 15502727
  8. Gallagher JC, Goldgar D: Treatment of postmenopausal osteoporosis with high doses of synthetic calcitriol. A randomized controlled study. Ann Intern Med. 1990 Nov 1;113(9):649-55. Pubmed: 2221645
  9. Lehmann B, Sauter W, Knuschke P, Dressler S, Meurer M: Demonstration of UVB-induced synthesis of 1 alpha,25-dihydroxyvitamin D3 (calcitriol) in human skin by microdialysis. Arch Dermatol Res. 2003 Apr;295(1):24-8. Epub 2003 Mar 11. Pubmed: 12709817
  10. Moreno J, Krishnan AV, Swami S, Nonn L, Peehl DM, Feldman D: Regulation of prostaglandin metabolism by calcitriol attenuates growth stimulation in prostate cancer cells. Cancer Res. 2005 Sep 1;65(17):7917-25. Pubmed: 16140963
  11. Kalkwarf HJ, Specker BL, Heubi JE, Vieira NE, Yergey AL: Intestinal calcium absorption of women during lactation and after weaning. Am J Clin Nutr. 1996 Apr;63(4):526-31. Pubmed: 8599316

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name:
CYP27B1
Uniprot ID:
O15528
Molecular weight:
56503.475
Reactions
Calcidiol + NADPH + Oxygen → Calcitriol + NADP + Waterdetails
Calcidiol + Oxygen + NADPH + Hydrogen Ion → Calcitriol + NADP + Waterdetails
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
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
Reactions
Calcitriol + NADPH + Oxygen → 24-Hydroxycalcitriol + NADP + Waterdetails
Calcitriol + NADPH + Hydrogen Ion + Oxygen → 24-Hydroxycalcitriol + NADP + Waterdetails