Showing metabocard for Ergocalciferol (BMDB0000900)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
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Record Information
Version1.0
Creation Date2016-09-30 22:38:19 UTC
Update Date2020-06-04 20:39:02 UTC
MCDB ID BMDB0000900
Secondary Accession Numbers
  • BMDB00900
Metabolite Identification
Common NameErgocalciferol
DescriptionErgocalciferol, also known as vitamin D2 or viosterol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, ergocalciferol is considered to be a secosteroid lipid molecule. Ergocalciferol is a drug which is used for use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin d resistant rickets). this drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin d dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with fanconi syndrome (with treatment of acidosis). Ergocalciferol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Ergocalciferol is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Nameergocalciferol
CAS Registry Number50-14-6
SMILES
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C
InChI Identifier
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
InChI KeyMECHNRXZTMCUDQ-RKHKHRCZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives 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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point116.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.05 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.59ALOGPS
logP7.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.89 m³·mol⁻¹ChemAxon
Polarizability50.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Concentrations
HMDB IDHMDB0000900
DrugBank IDDB00153
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012811
KNApSAcK IDNot Available
Chemspider ID4444351
KEGG Compound IDC05441
BioCyc IDVITAMIN_D2
BiGG ID2289183
Wikipedia LinkErgocalciferol
METLIN ID5856
PubChem Compound5280793
PDB IDNot Available
ChEBI ID28934
References
Synthesis ReferenceOkabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  2. Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen (1995). Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399. J. Agric. Food Chem.
  3. Fooddata+, The Technical University of Denmark (DTU) [Link]
  4. Fooddata+, The Technical University of Denmark (DTU) [Link]
  5. Fooddata+, The Technical University of Denmark (DTU) [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]
  7. Fooddata+, The Technical University of Denmark (DTU) [Link]
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]
  9. Fooddata+, The Technical University of Denmark (DTU) [Link]
  10. Fooddata+, The Technical University of Denmark (DTU) [Link]