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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-07-11 15:20:21 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006720
Secondary Accession Numbers
  • HMDB06720
Metabolite Identification
Common Name23S,25-dihydroxyvitamin D3
Description23S,25-dihydroxyvitamin D3 (23S,25-(OH)2D3) is a circulating metabolite of vitamin D3 during vitamin D excess. During hypocalcemia or hypovitaminosis D, 25-OH-D3 is 1alpha-hydroxylated, primarily in kidney, to produce 1,25-(OH)2D3. 1,25-(OH)2D3 is a hormonally active form of vitamin D3 that enhances intestinal calcium transport and promotes mobilization of calcium from bone. In states of vitamin D excess, other pathways of 25-OH-D3 metabolism emerge as alternatives to 1-and 24-hydroxylation. Recently, 25-hydroxyvitamin D3-26,23-lactone (lactone) was identified as a major plasma metabolite in animals receiving large doses of vitamin D. Although the function of the lactone is not known, its 5-fold greater potency of binding to the plasma vitamin D carrier protein, relative to 25-OH-D3, suggests that it may, perhaps indirectly, contribute to vitamin D toxicity. This indicates the existence of an alternate route to lactone formation through a new 25-OH-D3 metabolite, 23,25-(OH)2D3. (PMID: 6286629 ).
Structure
Thumb
Synonyms
ValueSource
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triolHMDB
23,25-DihydroxycholecalciferolHMDB
23,25-Dihydroxyvitamin D3HMDB
23S,25-Dihydroxyvitamin DHMDB
23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23R)-isomerMeSH, HMDB
23S, 25 Dihydroxyvitamin DMeSH, HMDB
23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23S)-isomerMeSH, HMDB
23S,25-Dihydroxyvitamin D3MeSH
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol
Traditional Name23,25-dihydroxyvitamin d3
CAS Registry Number77733-16-5
SMILES
OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C
InChI Identifier
InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1
InChI KeyJVBPQHSRTHJMLM-UXHBOMOISA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024038
KNApSAcK IDNot Available
Chemspider ID35016021
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13072270
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE2201
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Napoli JL, Pramanik BC, Partridge JJ, Uskokovic MR, Horst RL: 23S,25-dihydroxyvitamin D3 as a circulating metabolite of vitamin D3. Its role in 25-hydroxyvitamin D3-26,23-lactone biosynthesis. J Biol Chem. 1982 Aug 25;257(16):9634-9. [PubMed:6286629 ]