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Record Information
Version4.0
Creation Date2006-08-16 15:04:29 UTC
Update Date2017-09-27 08:22:07 UTC
HMDB IDHMDB0001438
Secondary Accession Numbers
  • HMDB01438
Metabolite Identification
Common Name25-Hydroxyvitamin D2
Description9,10-Secoergosta-5,7,10(19),22-tetraene-3,25-diol. Biologically active metabolite of vitamin D2 which is more active in curing rickets than its parent. The compound is believed to attach to the same receptor as vitamin D2 and 25-hydroxyvitamin D3.
Structure
Thumb
Synonyms
ValueSource
25-HydroxycalciferolHMDB
25-HydroxyergocalciferolHMDB
25-Hydroxyvitamin DHMDB
9,10-Secoergosta-5,7,10(19),22-tetraene-3b,25-diolHMDB
ErcalcidiolHMDB
25 HydroxycalciferolMeSH
9,10-Secoergosta-5,7,10(19),22-tetraene-3 beta,25-diolMeSH
25 Hydroxyvitamin D2MeSH
25-Hydroxyvitamin D 2MeSH
25 Hydroxyvitamin D 2MeSH
25 HydroxyergocalciferolMeSH
Chemical FormulaC28H44O2
Average Molecular Weight412.6478
Monoisotopic Molecular Weight412.334130652
IUPAC Name(1S,3Z)-3-{2-[(3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Name25-hydroxyvitamin D
CAS Registry Number21343-40-8
SMILES
C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/b11-9+,22-12+,23-13-/t20-,21+,24+,25?,26+,28-/m1/s1
InChI KeyKJKIIUAXZGLUND-BJWBXCNSSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as vitamin d and derivatives. These 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 effect

Health effect:

  Health condition:

    Renal and urinary disorders:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.002 g/LALOGPS
logP6.53ALOGPS
logP5.66ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.65 m³·mol⁻¹ChemAxon
Polarizability51.25 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0119200000-6a31a4086362269024cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-0459000000-45ba752a30c854da68ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fj4-6395000000-2a0bb52b37082e56a80eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0005900000-3e4d6f3ace31e3d64321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-1009500000-7f5a0d3322017b58bde3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9208000000-069f4c813e56ffb20663View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0023 +/- 0.00033 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0097 (0.002-0.017) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0032 (0.0022-0.0042) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0085 +/- 0.0295 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0879 +/- 0.023 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0347 +/- 0.0112 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.000011 +/- 0.0000099 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0037 +/- 0.0016 uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome details
BloodDetected and Quantified0.046 (0.024-0.069) uMAdult (>18 years old)BothAnephrism details
UrineDetected and Quantified0.0003 (0.000017-0.00065) umol/mmol creatinineAdult (>18 years old)BothNephrotic syndrome 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 ]
Nephrotic syndrome
  1. Sato KA, Gray RW, Lemann J Jr: Urinary excretion of 25-hydroxyvitamin D in health and the nephrotic syndrome. J Lab Clin Med. 1982 Mar;99(3):325-30. [PubMed:6977006 ]
Smith-Lemli-Opitz syndrome
  1. Rossi M, Federico G, Corso G, Parenti G, Battagliese A, Frascogna AR, Della Casa R, Dello Russo A, Strisciuglio P, Saggese G, Andria G: Vitamin D status in patients affected by Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2005;28(1):69-80. [PubMed:15702407 ]
Associated OMIM IDs
  • 270400 (Smith-Lemli-Opitz syndrome)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022621
KNApSAcK IDNot Available
Chemspider ID17216121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2289188
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833566
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceSardina, F. Javier; Mourino, Antonio; Castedo, Luis. Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2. Journal of Organic Chemistry (1986), 51(8), 1264-9.
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]