Calcitroic acid (CHEM022531)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:44 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022531
Identification
Common NameCalcitroic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass374.514 g/mol
Monoisotopic Mass374.246 g/mol
CAS Registry Number71204-89-2
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1039000000-1f88c71835fdec009978Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-1100290000-baa5a03a90d912185f1cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a70-0019000000-cb5546f5b2dabfd4d572Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0459000000-b307bdc6f267458bae7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-2692000000-5836da83c653fc8f7abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-f06abff6056eb86b8f3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c00-1009000000-ddade7030a96941096fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7309000000-add77990ddb49e71f86dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0389000000-7f28baeb8809349c3201Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0192000000-29b56ddbc29d3acf9008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mx-3970000000-cea41e29508e68bf1125Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-2ede4546d5bd0240a5ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-6009000000-fa722a798506a9889a5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-8926000000-85a3cc1c3ea55c628074Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006472
FooDB IDFDB023930
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2290389
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCalcitroic acid
Chemspider ID17216369
ChEBI IDNot Available
PubChem Compound ID12918533
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sakaki 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.
2. Reddy GS, Tserng KY: Calcitroic acid, end product of renal metabolism of 1,25-dihydroxyvitamin D3 through C-24 oxidation pathway. Biochemistry. 1989 Feb 21;28(4):1763-9.
3. Siu-Caldera ML, Zou L, Ehrlich MG, Schwartz ER, Ishizuka S, Reddy GS: Human osteoblasts in culture metabolize both 1 alpha, 25-dihydroxyvitamin D3 and its precursor 25-hydroxyvitamin D3 into their respective lactones. Endocrinology. 1995 Oct;136(10):4195-203.