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Record Information
Version3.6
Creation Date2007-05-22 18:20:36 UTC
Update Date2013-05-29 19:43:06 UTC
HMDB IDHMDB06225
Secondary Accession NumbersNone
Metabolite Identification
Common NameErcalcitriol
DescriptionErcalcitriol is the active circulating metabolite of vitamin D2. Vitamin D2 is modified by 25-hydroxylase in the liver and 25-hydroxyvitamin D *-hydroxylase in the kidney to form the active metabolite, ercalcitriol, which is then metabolized by 25-hydroxyvitamin D-24-hydroxylase (24-OHase, CYP24A1, EC 1.14.13.13). The binding of ercalcitriol or their analogs to Vitamin D receptor (VDR), a nuclear receptor, activates VDR to interact with retinoid X receptor (RXR) and forms the VDR/RXR/cofactor complex, which binds to Vitamin D response elements in the promoter region of target genes to regulate gene transcription. The kidney is the major site of 25-hydroxyvitamin D*-hydroxylase (CYP27B1, EC 1.14.13.13), which is responsible for the activation of 25-hydroxyvitamin D. Of all the steroid hormones, ercalcitriol represents the most difficult challenge to the analytical biochemist with respect to quantization. Ercalcitriol circulates at pmol concentrations, is highly lipophilic and its precursor, 25-hydroxyvitamin D2, circulates at nmol levels. (PMID: 16242929 , 17867378 , 17197173 ).
Structure
Thumb
Synonyms
  1. 1,25-Dihydroxycalciferol
  2. 1,25-Dihydroxyergocalciferol
  3. 1,25-Dihydroxyvitamin D2
  4. 1a,25-Dihydroxycalciferol
  5. 1a,25-Dihydroxyergocalciferol
  6. 1a,25-Dihydroxyvitamin D2
  7. Ro 17-6218
Chemical FormulaC28H44O3
Average Molecular Weight428.6472
Monoisotopic Molecular Weight428.329045274
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
CAS Registry Number60133-18-8
SMILES
C[C@H](\C=C\[C@H](C)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/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1
InChI KeyZGLHBRQAEXKACO-XJRQOBMKSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassVitamin D and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Sesterterpenes
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Tertiary Alcohol
Direct ParentVitamin D and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Mitochondria
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 Solubility0.007 g/LALOGPS
logP5.45ALOGPS
logP4.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity132.12ChemAxon
Polarizability52.28ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB023845
KNApSAcK IDNot Available
Chemspider ID7826183
KEGG Compound IDNot Available
BioCyc IDALPHA-RIBAZOLE
BiGG ID2289254
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06225
Metagene LinkHMDB06225
METLIN IDNot Available
PubChem Compound9547243
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSicinski, Rafal R.; Tanaka, Yoko; Schnoes, Heinrich K.; DeLuca, Hector F. Synthesis of 1a, 25-dihydroxyvitamin D2, its 24 epimer and related isomers, and their binding affinity for the 1,25-dihydroxyvitamin D3 receptor. Bioorganic Chemistry (1985), 13(2), 158-69.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakane M, Fey TA, Dixon DB, Ma J, Brune ME, Li YC, Wu-Wong JR: Differential effects of Vitamin D analogs on bone formation and resorption. J Steroid Biochem Mol Biol. 2006 Jan;98(1):72-7. Epub 2005 Oct 20. Pubmed: 16242929
  2. Hollis BW: Assessment of circulating 25(OH)D and 1,25(OH)2D: emergence as clinically important diagnostic tools. Nutr Rev. 2007 Aug;65(8 Pt 2):S87-90. Pubmed: 17867378
  3. Hollis BW, Horst RL: The assessment of circulating 25(OH)D and 1,25(OH)2D: where we are and where we are going. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):473-6. Epub 2007 Jan 2. Pubmed: 17197173

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
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