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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 10:53:13 UTC
Update Date2020-02-26 21:26:25 UTC
HMDB IDHMDB0006472
Secondary Accession Numbers
  • HMDB06472
Metabolite Identification
Common NameCalcitroic acid
DescriptionCalcitroic acid (1 alpha-hydroxy-23 carboxy-24,25,26,27-tetranorvitamin D(3)) is a metabolite of 1 alpha, 25-dihydroxyvitamin D(3) (calcitriol). It is soluble in water, and is excreted in urine. This deactivation process involves a series of oxidation reactions at C24 and C23 leading to side-chain cleavage and, ultimately, formation of the calcitroic acid. This deactivation involves the loss of carbons 24, 25, 26, and 27 and the oxidation of carbon 23 to a carboxylic acid. Calcitroic acid is also a major terminal product for the deactivation of 1α,25-dihydroxyvitamin D2. Both the kidney and the intestine metabolize 1,25-dihydroxyvitamin D3 through the C-24 oxidation pathway according to the following steps: 1,25-dihydroxyvitamin D3----1,24,25-trihydroxyvitamin D3----1,25-dihydroxy-24-oxovitamin D3-----1,23,25-trihydroxy-24-oxovitamin D3 (PMID: 2719932 ). The C-24 oxidation pathway leading to the formation of calcitroic acid has been reported to be present in bone cells, but the C-23 oxidation pathway leading to the formation of 1 alpha, 25-(OH)2D3-26,23-lactone has not been described in bone cells, even though 1 alpha, 25-(OH)2D3-26,23-lactone is noted to have a significant effect on bone formation. (PMID: 7664636 ).
Structure
Data?1582752385
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
Calcitroic acidHMDB
(3R)-3-[(1R,3AS,4E,7ar)-4-{2-[(1E,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]butanoateGenerator
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 References
  1. 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. [PubMed:2719932 ]
  2. 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. [PubMed:7664636 ]