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Record Information
Version3.6
Creation Date2007-05-23 12:26:48 UTC
Update Date2016-02-11 01:07:32 UTC
HMDB IDHMDB06500
Secondary Accession NumbersNone
Metabolite Identification
Common NamePrevitamin D3
DescriptionPrevitamin D3 is an intermediate in the production of Vitamin D.
Structure
Thumb
Synonyms
ValueSource
(3beta,6Z)-9,10-Secocholesta-5(10),6,8-trien-3-olHMDB
(6Z)-(3S)-9,10-seco-5(10),6,8-Cholestatrien-3-olHMDB
Previtamin D(3)HMDB
Previtamin d_3 / precholecalciferol / (6Z)-tacalciolHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(1S)-3-[(Z)-2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
Traditional Name(1S)-3-[(Z)-2-[(1R,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
CAS Registry Number1173-13-3
SMILES
CC(C)CCC[C@@H](C)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C/C1=C(C)CC[C@H](O)C1
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/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12-/t21-,24+,25-,26?,27-/m1/s1
InChI KeyInChIKey=YUGCAAVRZWBXEQ-QEYGBBHESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but 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
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility0.000374 mg/mLALOGPS
logP7.38ALOGPS
logP7.07ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity124.3 m3·mol-1ChemAxon
Polarizability48.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB023943
KNApSAcK IDNot Available
Chemspider ID9375051
KEGG Compound IDC07711
BioCyc IDNot Available
BiGG ID2288991
Wikipedia LinkPrevitamin D3
NuGOwiki LinkHMDB06500
Metagene LinkHMDB06500
METLIN IDNot Available
PubChem Compound11199982
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceVelluz, Leon; Amiard, Gaston. Precursors for vitamin D2 or calciferol and for vitamin D3. (1952), FR 999987 19520206 CAN 51:30144 AN 1957:30144
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available