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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-16 14:44:20 UTC
Update Date2018-05-19 21:37:42 UTC
HMDB IDHMDB0001420
Secondary Accession Numbers
  • HMDB01420
Metabolite Identification
Common Name25,26-dihydroxyvitamin D
Description25,26-(OH)2D3 is a renal microsomal 25-OH-D3 metabolite, whose plasma concentration increases during vitamin D excess concomitantly with an increase in the concentration of lactone. This observation considered with the related structural features of 25,26-(OH)2D3 and lactone (both are oxidized at (C-26) suggested that 25,26(OH)2D3, a metabolite of unknown function, could be a precursor to lactone. In fact, it has been reported that functionalization of C-26 and subsequent lactone formation occurs exclusively in kidney. However, rigorous examination has unambiguously excluded 25S,26-(OH)2D3, the naturally occurring form as a significant lactone precursor. (PMID: 6286629 ).
Structure
Thumb
Synonyms
ValueSource
25,26-DihydroxycholecalciferolHMDB
25,26-Dihydroxyvitamin D3HMDB
9,10-Secocholesta-5,7,10(19)-triene-3b,25,26-triolHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(6R)-6-[(1R,3aS,5Z,7aS)-5-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-1,2-diol
Traditional Name25,26-dihydroxyvitamin D
CAS Registry Number29261-12-9
SMILES
[H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)(O)CO)[C@@]1(C)CC\C(C2)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O3/c1-19-7-11-24(29)17-22(19)9-8-21-13-15-27(4)23(16-21)10-12-25(27)20(2)6-5-14-26(3,30)18-28/h8-9,20,23-25,28-30H,1,5-7,10-18H2,2-4H3/b21-8-,22-9-/t20-,23+,24+,25-,26?,27+/m1/s1
InChI KeyWWGCQHXFACVYPT-JKVVTCAUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.0078 g/LALOGPS
logP5.14ALOGPS
logP4.61ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity126.6 m³·mol⁻¹ChemAxon
Polarizability52.3 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0fbj-2029200000-8c64c3a766c1242a4f93View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1223049000-838b1768e3cf26ce4cfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0119300000-69bff8e97accbd9ea4c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05aj-0259000000-34623fae8b6c2c8399d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-4296000000-41ad31b1fb8e4977bbf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-ceec977aa9fd67db2b61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009200000-39daf19c493a5738c699View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-7009000000-901d5cae36e6a90f22c6View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00168 (0.000480-0.00288) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00120 (0.000720-0.00168) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0019 +/- 0.001 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00144 (0.000720-0.00216) uMAdult (>18 years old)BothAnephrism details
Associated Disorders and Diseases
Disease References
Anephric patients
  1. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69. [PubMed:227368 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021794
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477727
PDB IDNot Available
ChEBI ID89079
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69. [PubMed:227368 ]
  2. 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 ]