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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 18:32:06 UTC
Update Date2017-12-07 01:55:50 UTC
HMDB IDHMDB0006228
Secondary Accession Numbers
  • HMDB06228
Metabolite Identification
Common Name24-Hydroxycalcitriol
Description24-Hydroxycalcitriol stimulates intestinal calcium transport but not bone calcium mobilization or phosphate transport reactions. (PMID: 163578 ). Vitamin D-24-hydroxylase (24-OHase) is a cytochrome P-450 enzyme that catalyzes the conversion of 1alpha,25-dihydroxyvitamin D3 [1,25-(OH)2D3] to 24-Hydroxycalcitriol (1,24,25-trihydroxyvitamin D3). (PMID: 9165006 ). The administration of 24-Hydroxycalcitriol at doses of 0.2 and 0.3 microg/kg/day produced strong anabolic effects, especially on vertebral cancellous bone that can prevent estrogen depletion-induced bone loss in ovariectomized (OVX) rats. (PMID: 9115161 ).
Structure
Thumb
Synonyms
ValueSource
1alpha,24R,25(OH)3D3ChEBI
1alpha,24R,25-TrihydroxycholecalciferolChEBI
1alpha,24R,25-Trihydroxyvitamin D3ChEBI
1a,24R,25(OH)3D3Generator
1α,24R,25(OH)3D3Generator
1a,24R,25-TrihydroxycholecalciferolGenerator
1α,24R,25-trihydroxycholecalciferolGenerator
1a,24R,25-Trihydroxyvitamin D3Generator
1α,24R,25-trihydroxyvitamin D3Generator
(1-alpha,3-beta,5Z,7E,24R)-10-Secocholesta-5,7,10(19)-triene-1,3,24,25-tetrolHMDB
(1-alpha,3-beta,5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,24,25-tetrolHMDB
(24R)-24-HydroxycalcitriolHMDB
1-alpha,24(R),25-Trihydroxyvitamin D3HMDB
1-alpha,24R,25-Trihydroxyvitamin D3HMDB
CalcitetrolHMDB
ro 21-7729HMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.6359
Monoisotopic Molecular Weight432.323959896
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Namecalcitetrol
CAS Registry Number56142-94-0
SMILES
C[C@H](CC[C@@H](O)C(O)(C)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
InChI Identifier
InChI=1S/C27H44O4/c1-17(8-13-25(30)26(3,4)31)22-11-12-23-19(7-6-14-27(22,23)5)9-10-20-15-21(28)16-24(29)18(20)2/h9-10,17,21-25,28-31H,2,6-8,11-16H2,1,3-5H3/b19-9+,20-10-/t17-,21-,22-,23+,24+,25-,27-/m1/s1
InChI KeyWFZKUWGUJVKMHC-UKBUZQLGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vitamin d and derivatives. These 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP4.39ALOGPS
logP3.28ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.74ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity127.89 m³·mol⁻¹ChemAxon
Polarizability52.13 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-8019800000-bd957cd71fdc43e3cf94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-2212039000-ff7c0fc06a74f042ea4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0119800000-971c62e3a9b445085374View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0329200000-87fe5af08f7d613843adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ta-1249100000-e02dd2ffb8dcfe6ac44dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-1a4a0abd4a0f9c808d15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-0006900000-f4091fa625ee0575ca96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-9005200000-f5bbc4087082427238c7View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023848
KNApSAcK IDNot Available
Chemspider ID4949843
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2290333
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6446280
PDB IDNot Available
ChEBI ID47799
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. DeLuca HF: The kidney as an endocrine organ involved in the function of vitamin D. Am J Med. 1975 Jan;58(1):39-47. [PubMed:163578 ]
  2. Akeno N, Saikatsu S, Kawane T, Horiuchi N: Mouse vitamin D-24-hydroxylase: molecular cloning, tissue distribution, and transcriptional regulation by 1alpha,25-dihydroxyvitamin D3. Endocrinology. 1997 Jun;138(6):2233-40. [PubMed:9165006 ]
  3. Erben RG, Bante U, Birner H, Stangassinger M: Prophylactic effects of 1,24,25-trihydroxyvitamin D3 on ovariectomy-induced cancellous bone loss in the rat. Calcif Tissue Int. 1997 May;60(5):434-40. [PubMed:9115161 ]

Enzymes

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