Showing metabocard for Vitamin D3 (BMDB0000876)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:37:55 UTC
Update Date2020-06-04 20:48:42 UTC
MCDB ID BMDB0000876
Secondary Accession Numbers
  • BMDB00876
Metabolite Identification
Common NameVitamin D3
DescriptionVitamin D3 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. Vitamin D3 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Vitamin D3HMDB
(3beta,Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-olHMDB
(5E,7E)-9,10-Secocholesta-5,7,10-trien-3-olHMDB
3-beta,Z,7E-9,10-Secocholestr-5,7,10(19)-trien-3-olHMDB
9,10-Secocholesta-5,7,10(19)-trien-3-beta-olHMDB
9,10-Secocholesta-5,7,10(19)-trien-3-olHMDB
9,10-Secocholesta-5,7,10-trien-3-olHMDB
ArachitolHMDB
CalciolHMDB
CCHMDB
CholecalciferolHMDB
Cholecalciferol D3HMDB
ColecalciferolHMDB
D3-VigantolHMDB
DelsterolHMDB
DeparalHMDB
DevaronHMDB
EbivitHMDB
FeraColHMDB
Granuvit D3HMDB
micro-DeeHMDB
Oleovitamin D3HMDB
ProvitinaHMDB
QuintoxHMDB
RicketonHMDB
TrivitanHMDB
Vi-de3HMDB
VidDe-3-hydrosolHMDB
VidekholHMDB
VigantolHMDB
VigorsanHMDB
Vitinc dan-dee-3HMDB
(3 beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-olMeSH
CholecalciferolsMeSH
Vitamin D 3MeSH
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S,3Z)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Namerampage
CAS Registry Number67-97-0
SMILES
CC(C)CCC[C@@H](C)[C@H]1CCC2\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-QWSSABAFSA-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 DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.22 m³·mol⁻¹ChemAxon
Polarizability49.44 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-3029000000-1950c74de34369a704002017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-002f-9207800000-c6f808a014153de38d582017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0129000000-442693b5a55274aeb0b32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c09-3496000000-bf01a7ddf350733d39f22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8298000000-b9136b2dd6e2c22c11232017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-70ba08bf3cd328c6087e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-c16445787a057993951a2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-1239000000-328f37347d493ff8f54a2017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.00052 uM
  • Pirjo H. Mattila,...
 details
Detected and Quantified0.00013 uM details
Detected and Quantified0.00013 uM details
Detected and Quantified0.00018 uM details
Detected and Quantified0.00198 uM details
Detected and Quantified0.00018 uM details
Detected and Quantified0.0026 uM details
Detected and Quantified0.00023 uM details
Detected and Quantified0.00021 uM details
Detected and Quantified0.0147 +/- 0.0002 uM details
Detected and Quantified0.019 +/- 0.001 uM details
Detected and Quantified0.0435 +/- 0.0002 uM details
Detected and Quantified0.015 +/- 0.001 uM details
HMDB IDHMDB0014315
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCholecalciferol
METLIN IDNot Available
PubChem Compound10883523
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNemoto, Hideo; Kurobe, Hiroshi; Fukumoto, Keiichiro; Kametani, Tetsuji. A modified synthesis of the (+)-8a-phenylsulfonyl-des-AB-cholestane via an intramolecular nucleophilic attack to epoxide - a total synthesis of vitamin D3. Heterocycles (1985), 23(3),
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]