Human Metabolome Database Version 3.5

Showing metabocard for Calcitriol (HMDB01903)

Record Information
Version 3.5
Creation Date 2006-03-10 03:07:06 -0700
Update Date 2013-02-08 17:10:59 -0700
HMDB ID HMDB01903
Secondary Accession Numbers None
Metabolite Identification
Common Name Calcitriol
Description The 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C27H44O3
Average Molecular Weight 416.6365
Monoisotopic Molecular Weight 416.329045274
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 IUPAC Name calcitriol
CAS Registry Number 32222-06-3
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 Key GMRQFYUYWCNGIN-NKMMMXOESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Sesterterpenes
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Vitamin D and Derivatives
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Steroid
  • Tertiary Alcohol
Direct Parent Sesterterpenes
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 113 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0067 g/L ALOGPS
LogP 5.51 ALOGPS
LogP 4.35 ChemAxon
LogS -4.80 ALOGPS
pKa (strongest acidic) 14.39 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 60.69 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 126.53 ChemAxon
Polarizability 51.52 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Prostate
  • Skin
  • Adrenal Medulla
  • Gonads
  • Gut
  • Spleen
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.000086 (0.000029-0.00016) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.000074 (0.000052-0.000096) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021822
KNApSAcK ID Not Available
Chemspider ID 4444108 Link_out
KEGG Compound ID C01673 Link_out
BioCyc ID CALCITRIOL Link_out
BiGG ID 2289241 Link_out
Wikipedia Link Calcitriol Link_out
NuGOwiki Link HMDB01903 Link_out
Metagene Link HMDB01903 Link_out
METLIN ID 6382 Link_out
PubChem Compound 5280453 Link_out
PDB ID VDX Link_out
ChEBI ID 17823 Link_out
References
Synthesis Reference Chen, 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. 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 Link_out
  2. 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 Link_out
  3. Mallette LE: Case report: hypoparathyroidism with menses-associated hypocalcemia. Am J Med Sci. 1992 Jul;304(1):32-7. Pubmed: 1642251 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out

Enzymes
Name: 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial
Reactions:
Calcidiol + NADPH + Oxygen unknown Calcitriol + NADP + Water details
Calcidiol + Oxygen + NADPH + Hydrogen Ion unknown Calcitriol + NADP + Water details
Gene Name: CYP27B1
Uniprot ID: O15528 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Vitamin D3 receptor
Reactions: Not Available
Gene Name: VDR
Uniprot ID: P11473 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
Reactions:
Calcitriol + NADPH + Oxygen unknown 24-Hydroxycalcitriol + NADP + Water details
Calcitriol + NADPH + Hydrogen Ion + Oxygen unknown 24-Hydroxycalcitriol + NADP + Water details
Gene Name: CYP24A1
Uniprot ID: Q07973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA