Showing metabocard for Ercalcitriol (BMDB0006225)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:34 UTC
Update Date2020-04-22 15:16:58 UTC
BMDB IDBMDB0006225
Secondary Accession Numbers
  • BMDB06225
Metabolite Identification
Common NameErcalcitriol
DescriptionErcalcitriol, also known as 1,25-(OH)2D2, 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, ercalcitriol is considered to be a secosteroid lipid molecule. Ercalcitriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,25-DihydroxycalciferolChEBI
1,25-DihydroxyergocalciferolChEBI
1,25-Dihydroxyvitamin D2ChEBI
1alpha,25-DihydroxycalciferolChEBI
1alpha,25-DihydroxyergocalciferolChEBI
1a,25-DihydroxycalciferolGenerator
1Α,25-dihydroxycalciferolGenerator
1a,25-DihydroxyergocalciferolGenerator
1Α,25-dihydroxyergocalciferolGenerator
1a,25-Dihydroxyvitamin D2 / 1a,,25-dihydroxyergocalciferolHMDB
1Α,25-dihydroxyvitamin D2 / 1α,,25-dihydroxyergocalciferolHMDB
1 alpha,25-Dihydroxyvitamin D2HMDB
1,25-Dihydroxyergocalciferol, (1alpha,3beta,5Z,7E,22E)-isomerHMDB
1,25-(OH)2D2HMDB
ErcalcitriolChEBI
1a,25-Dihydroxyvitamin D2Generator
1Α,25-dihydroxyvitamin D2Generator
Chemical FormulaC28H44O3
Average Molecular Weight428.6472
Monoisotopic Molecular Weight428.329045274
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
CAS Registry Number60133-18-8
SMILES
C[C@H](\C=C\[C@H](C)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C
InChI Identifier
InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1
InChI KeyZGLHBRQAEXKACO-XJRQOBMKSA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.45ALOGPS
logP4.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity132.12 m³·mol⁻¹ChemAxon
Polarizability52.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-4029600000-dbfa8697870ebd683025View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-003r-1400149000-b8a11d6c4c1ad554146eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0119800000-7dd9f14f9a8c59dc34daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gvx-1329200000-0a0f4f399ef35e7f8039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-4449200000-6bc7143e80424071bd59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-01f91a65a26969417dc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0004900000-35bc1dcb432dd5b31686View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i09-7109200000-c0e2fe47359423d7eee0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-be3d96e63cee98d539bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1402900000-1f6915f21eef2875a071View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-2319300000-299bc94defd194cd6facView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0193200000-a4d6e13ad596312a24b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1094000000-5a9b3afb3048a2dde8d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y0-4982000000-9e151864bb3f37c45627View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006225
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023845
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547243
PDB IDNot Available
ChEBI ID86320
References
Synthesis ReferenceSicinski, Rafal R.; Tanaka, Yoko; Schnoes, Heinrich K.; DeLuca, Hector F. Synthesis of 1a, 25-dihydroxyvitamin D2, its 24 epimer and related isomers, and their binding affinity for the 1,25-dihydroxyvitamin D3 receptor. Bioorganic Chemistry (1985), 13(2), 158-69.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available