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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2013-02-09 00:31:15 UTC
HMDB IDHMDB14315
Secondary Accession NumbersNone
Metabolite Identification
Common NameCholecalciferol
DescriptionCholecalciferol is only found in individuals that have used or taken this drug. It is a derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. [PubChem]The first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. The active form of vitamin D3 (calcitriol) binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
Structure
Thumb
Synonyms
  1. (+)-vitamin D3
  2. Calciol
  3. CC
  4. Colecalciferol
  5. Vitamin D3
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional IUPAC Namevitamin D3
CAS Registry Number67-97-0
SMILES
CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1
InChI KeyQYSXJUFSXHHAJI-YRZJJWOYSA-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
Direct ParentSesterterpenes
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antihypocalcemic Agents
  • Antihypoparathyroid Agents
  • Bone Density Conservation Agents
  • Cell signaling
  • Essential Vitamin
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Vitamins
  • Vitamins (Vitamin D)
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.80e-04 g/LNot Available
LogP7.5Not Available
Predicted Properties
PropertyValueSource
water solubility3.800E-04 g/LALOGPS
logP7.98ALOGPS
logP7.13ChemAxon
logS-6ALOGPS
pKa (strongest acidic)18.38ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count6ChemAxon
refractivity123.22ChemAxon
polarizability49.6ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00169
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00169
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00169
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444353
KEGG Compound IDC05443
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCholecalciferol
NuGOwiki LinkHMDB14315
Metagene LinkHMDB14315
METLIN IDNot Available
PubChem Compound5280795
PDB IDNot Available
ChEBI ID28940
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3).
Gene Name:
CYP2R1
Uniprot ID:
Q6VVX0
Molecular weight:
57358.82
Reactions
Cholecalciferol + Oxygen + NADPH → Calcidiol + NADP(+) H(2)Odetails
Calcidiol + NADP + Water → Cholecalciferol + NADPH + Hydrogen Ion + Oxygendetails