Record Information
Version1.0
Creation date2011-04-06 18:26:21 UTC
Update date2019-11-26 03:20:52 UTC
Primary IDFDB021782
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name25-Hydroxycholecalciferol
DescriptionCalfcifediol is a prehormone that is produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme cholecalciferol 25-hydroxylase. Calcifediol is then converted in the kidneys into calcitriol (1,25-(OH)2D3), a secosteroid hormone that is the active form of vitamin D. It can also be converted into 24-hydroxycalcidiol in the kidneys via 24-hydroxylation. [Wikipedia]. 25-Hydroxycholecalciferol is found in many foods, some of which are green zucchini, green bell pepper, red bell pepper, and other animal fat.
CAS Number19356-17-3
Structure
Thumb
Synonyms
SynonymSource
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-triene-3,25-diolChEBI
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
25(OH)D3ChEBI
25-HydroxycholecalciferolChEBI
25-Hydroxyvitamin D3ChEBI
3-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexanolChEBI
CalcifediolChEBI
Calcifediol anhydrousChEBI
CalcifediolumChEBI
RayaldeeChEBI
(3S,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-3,25-diolKegg
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolGenerator
(3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diolGenerator
25-Hydroxy-cholecalciferolHMDB
5,6-cis-25-Hydroxyvitamin D3HMDB
9,10-Secocholesta-5,7,10(19)-triene-3b,25-diolHMDB
CalderolHMDB
DidrogylHMDB
HidroferolHMDB
25 Hydroxyvitamin D3HMDB
Calcifediol, (3 beta,5E,7E)-isomerHMDB
Monohydrate, 25-hydroxycholecalciferolHMDB
25-Hydroxycholecalciferol monohydrateHMDB
Anhydrous, calcifediolHMDB
Organon brand OF calcifediolHMDB
25 Hydroxyvitamin D 3HMDB
25-Hydroxyvitamin D 3HMDB
Aventis brand OF calcifediolHMDB
Calcifediol aventis brandHMDB
Calcifediol organon brandHMDB
DedrogylHMDB
25 HydroxycholecalciferolHMDB
25 Hydroxycholecalciferol monohydrateHMDB
Calcifediol faes brandHMDB
Calcifediol, (3 alpha,5Z,7E)-isomerHMDB
Faes brand OF calcifediolHMDB
CalcidiolMeSH
(3b,5Z,7e)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolGenerator
(3beta,5Z,7e)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
(3S,5Z,7e)-9,10-Secocholesta-5,7,10-triene-3,25-diolChEBI
(3β,5Z,7e)-9,10-secocholesta-5,7,10(19)-triene-3,25-diolGenerator
(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diolmanual
25-(OH)Dmanual
25-Hydroxyvitamin Dmanual
Delakminmanual
Diaverenemanual
Vitamin D, 25-hydroxycholecalciferolmanual
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP6.71ALOGPS
logP5.65ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.06 m³·mol⁻¹ChemAxon
Polarizability50.32 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H44O2
IUPAC name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
InChI IdentifierInChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChI KeyJWUBBDSIWDLEOM-DTOXIADCSA-N
Isomeric SMILESC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
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
  • Tertiary alcohol
  • 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

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2900000000-33a8e563016d6e2e358eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00lr-2900000000-f6bedf68127696063061JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2900000000-33a8e563016d6e2e358eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00lr-2900000000-f6bedf68127696063061JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3029000000-4c75b5cfbc422ba2a344JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-1403290000-a8eb9294a6df1ce864d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0119100000-d3e0a5d2ecb614d781d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0api-0369000000-146e7a23795c22f5b836JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-5296000000-412b0c2da61c93271acdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-ef5150b1dccaed2f9543JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0009000000-4b22b5c88dc06c01fe89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-2229000000-f4037186ef5a21a16859JSpectraViewer
ChemSpider ID4446820
ChEMBL IDCHEMBL1040
KEGG Compound IDC01561
Pubchem Compound ID5283731
Pubchem Substance IDNot Available
ChEBI ID17933
Phenol-Explorer IDNot Available
DrugBank IDDB00146
HMDB IDHMDB03550
CRC / DFC (Dictionary of Food Compounds) IDHLJ22-W:HMC07-T
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2289142
KNApSAcK IDNot Available
HET IDVDY
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCalcifediol
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General Reference
  1. Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. Pubmed [Isolation]
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).