Human Metabolome Database Version 3.5

Showing metabocard for Cholecalciferol (HMDB14315)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:49 -0600
Update Date 2013-02-08 17:31:15 -0700
HMDB ID HMDB14315
Secondary Accession Numbers None
Metabolite Identification
Common Name Cholecalciferol
Description Cholecalciferol 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-vitamin D3
  2. Calciol
  3. CC
  4. Colecalciferol
  5. Vitamin D3
Chemical Formula C27H44O
Average Molecular Weight 384.6377
Monoisotopic Molecular Weight 384.33921603
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 Name vitamin D3
CAS Registry Number 67-97-0
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 Key QYSXJUFSXHHAJI-YRZJJWOYSA-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
Direct Parent Sesterterpenes
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 84.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.80e-04 g/L Not Available
LogP 7.5 Not Available
Predicted Properties
Property Value Source
Water Solubility 3.800E-04 g/L ALOGPS
LogP 7.98 ALOGPS
LogP 7.13 ChemAxon
LogS -6.01 ALOGPS
pKa (strongest acidic) 18.38 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 123.22 ChemAxon
Polarizability 49.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00169
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00169
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00169 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4444353 Link_out
KEGG Compound ID C05443 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Cholecalciferol Link_out
NuGOwiki Link HMDB14315 Link_out
Metagene Link HMDB14315 Link_out
METLIN ID Not Available
PubChem Compound 5280795 Link_out
PDB ID Not Available
ChEBI ID 28940 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Vitamin D 25-hydroxylase
Reactions:
Cholecalciferol + Oxygen + NADPH unknown Calcidiol + NADP(+) H(2)O details
Calcidiol + NADP + Water unknown Cholecalciferol + NADPH + Hydrogen Ion + Oxygen details
Gene Name: CYP2R1
Uniprot ID: Q6VVX0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA