Showing metabocard for Calcitroic acid (BMDB0006472)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:22:20 UTC
Update Date2020-05-11 20:24:42 UTC
BMDB IDBMDB0006472
Secondary Accession Numbers
  • BMDB06472
Metabolite Identification
Common NameCalcitroic acid
DescriptionCalcitroic acid, also known as calcitroate, 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. Based on a literature review a significant number of articles have been published on Calcitroic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CalcitroateGenerator
(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoateHMDB
(3R)-3-[(1R,3AR,4E,7ar)- 4-[(2Z)-2-[(3R,5R)-3,5- dihydroxy-2-methylene-cyclohexylidene]ethylidene] -7a-methyl-2,3,3a,5,6,7-hexahydro-1H -inden-1-yl]butanoic acidHMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoateHMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-[(2Z)-2-[(3R,5S)-3,5-dihydroxy-2 methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butanoic acidHMDB
1 alpha-Hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)HMDB
1a-HydroxycalcioateHMDB
1a-Hydroxycalcioic acidHMDB
1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-OateHMDB
1alpha,3beta-Dihydroxy-24-nor-9,10-seco-5,7,10(19)-cholatrien-23-Oic acidHMDB
1alpha-Hydroxy-23-carboxytetranorvitamin DHMDB
Calcitroic acid (D3)HMDB
1 alpha,3 beta-Dihydroxy-24-nor-9,10- seco-5,7,10(19)-cholatrien-23-Oic acidHMDB
1 alpha-Hydroxy-23-carboxytetranorvitamin DHMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoateHMDB
Calcitroic acidHMDB
Chemical FormulaC23H34O4
Average Molecular Weight374.5137
Monoisotopic Molecular Weight374.245709576
IUPAC Name(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoic acid
Traditional Name(3R)-3-[(1R,3aS,4E,7aR)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]butanoic acid
CAS Registry Number71204-89-2
SMILES
[H][C@@]12CC[C@H]([C@H](C)CC(O)=O)[C@@]1(C)CCC\C2=C/C=C1\C[C@@H](O)C[C@H](O)C1=C
InChI Identifier
InChI=1S/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7+/t14-,18-,19-,20+,21+,23-/m1/s1
InChI KeyMBLYZRMZFUWLOZ-WLWRUGSRSA-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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP4.1ALOGPS
logP2.88ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.01 m³·mol⁻¹ChemAxon
Polarizability43.64 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, Positivesplash10-0a4i-1039000000-1f88c71835fdec009978View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-1100290000-baa5a03a90d912185f1cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0019000000-cb5546f5b2dabfd4d572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0459000000-b307bdc6f267458bae7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-2692000000-5836da83c653fc8f7abbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-f06abff6056eb86b8f3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c00-1009000000-ddade7030a96941096fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7309000000-add77990ddb49e71f86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0389000000-7f28baeb8809349c3201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0192000000-29b56ddbc29d3acf9008View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mx-3970000000-cea41e29508e68bf1125View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-2ede4546d5bd0240a5ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-6009000000-fa722a798506a9889a5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-8926000000-85a3cc1c3ea55c628074View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006472
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023930
KNApSAcK IDNot Available
Chemspider ID17216369
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2290389
Wikipedia LinkCalcitroic acid
METLIN IDNot Available
PubChem Compound12918533
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSakaki T; Sawada N; Nonaka Y; Ohyama Y; Inouye K Metabolic studies using recombinant escherichia coli cells producing rat mitochondrial CYP24 CYP24 can convert 1alpha,25-dihydroxyvitamin D3 to calcitroic acid. European journal of biochemistry / FEBS (1999), 262(1), 43-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available