Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2019-11-26 03:07:39 UTC
Primary IDFDB012811
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameErgocalciferol
DescriptionErgocalciferol, also known as oleovitamin 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 very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergocalciferol is a potentially toxic compound.
CAS Number50-14-6
Structure
Thumb
Synonyms
SynonymSource
(3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
Activated ergosterolChEBI
CalciferolChEBI
ErcalciolChEBI
ErgocalciferolumChEBI
Oleovitamin D2ChEBI
ViosterolChEBI
Vitamina D2ChEBI
Vitamin D2Kegg
DrisdolKegg
(3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(+)-Vitamin D2HMDB
(5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-olHMDB
22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-olHMDB
4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanolHMDB
9,10-Secoergosta-5,7,10(19),22-tetraen-3b-olHMDB
beta-OlHMDB
Buco-DHMDB
Calciferon 2HMDB
CondacapsHMDB
CondocapsHMDB
CondolHMDB
CrtronHMDB
CrystallinaHMDB
D-ArthinHMDB
D-TracettenHMDB
DaralHMDB
Davitamon DHMDB
DavitinHMDB
De-rat concentrateHMDB
DecapsHMDB
Dee-osterolHMDB
Dee-ronHMDB
Dee-ronalHMDB
Dee-roualHMDB
delta-ArthinHMDB
delta-TracettenHMDB
DeltalinHMDB
DeratolHMDB
DetalupHMDB
DiactolHMDB
Divit urtoHMDB
DoralHMDB
Ergocalciferol oilHMDB
ErgoroneHMDB
Ergosterol activatedHMDB
Ergosterol irradiatedHMDB
ErtronHMDB
FortodylHMDB
GeltabsHMDB
Hi-deratolHMDB
InfronHMDB
Irradiated ergosta-5,7,22-trien-3beta-olHMDB
MetadeeHMDB
Mina D2HMDB
MulsiferolHMDB
MykostinHMDB
Novovitamin-DHMDB
Oleovitamin DHMDB
OsteilHMDB
OstelinHMDB
RadiostolHMDB
RadsteinHMDB
RadsterinHMDB
Rodine CHMDB
Shock-ferolHMDB
Shock-ferol sterogylHMDB
SterogylHMDB
Synthetic vitamin DHMDB
Uvesterol DHMDB
Uvesterol-DHMDB
Vio DHMDB
Vio-DHMDB
ViostdrolHMDB
Viosterol in oilHMDB
Vitavel-DHMDB
CalciferolsHMDB
ErgocalciferolsHMDB
D2, VitaminHMDB
Vitamin D 2HMDB
ErgocalciferolChEBI
(3b,5Z,7e,22e)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(3beta,5Z,7e,22e)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10,22-tetraen-3-olbiospider
(3S,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-olbiospider
(3β,5Z,7e,22e)-9,10-secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(5e,7e,22e)-9,10-Secoergosta-5,7,10,22-tetraen-3-olHMDB
(5Z,7e,22e)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-olChEBI
(5Z,7e,22e)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
9,10-Seco(5Z,7E,22E)-5,7,10(19),22-ergostatetraen-3-olbiospider
Calciferol (vitamin D2)biospider
Ergocalciferol (D2)biospider
Ergocalciferol, BAN, INN, USANdb_source
Ergosterol (activated)db_source
Predicted Properties
PropertyValueSource
Water Solubility0.00043 g/LALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H44O
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
InChI IdentifierInChI=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
Isomeric SMILESCC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.79%; H 11.18%; O 4.03%DFC
Melting PointMp 114.5-117°DFC
Boiling PointNot Available
Experimental Water Solubility0.05 mg/mLTOMLIN,C (1994)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +102.5 (EtOH)DFC
Spectroscopic UV Data[neutral] lmax 265 () (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003u-3911000000-dba9e396497310b31715JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-3911000000-dba9e396497310b31715JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-3019000000-8a847f6179b3a364ad05JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-4103900000-4c6f376ae6706d7e8556JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0129000000-77bd32807ec8ea97183bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0601-5902000000-ae4a4363ac10f9f0feb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9800000000-1ea9f4fa17117a9e6515JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01ot-9801000000-17d2120d47f9c718ea95JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ot-9801000000-c10341d61ee2d6369219JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1129000000-41a3f60b47798eb6bd6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ai-4694000000-95577608302dfef840b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gx9-9464000000-f7bcbdb6e805513cd661JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-819b52cfd84baf07f550JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-5ed8b1f535a88d73555cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3249000000-bf201c27d3bc67289adbJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID4444351
ChEMBL IDCHEMBL1536
KEGG Compound IDC05441
Pubchem Compound ID5280793
Pubchem Substance IDNot Available
ChEBI ID28934
Phenol-Explorer IDNot Available
DrugBank IDDB00153
HMDB IDHMDB00900
CRC / DFC (Dictionary of Food Compounds) IDHGL83-Q:HLJ17-Y
EAFUS ID3857
Dr. Duke IDVITAMIN-D
BIGG ID2289183
KNApSAcK IDNot Available
HET IDD2V
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDErgocalciferol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
UMP-CMP kinase 2, mitochondrialCMPK2Q5EBM0
Cytosolic 5'-nucleotidase III-like proteinNT5C3LQ969T7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.