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Record Information
Version3.6
Creation Date2006-08-16 15:04:29 UTC
Update Date2016-02-11 01:04:40 UTC
HMDB IDHMDB01438
Secondary Accession NumbersNone
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
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 KeyInChIKey=KJKIIUAXZGLUND-BJWBXCNSSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing 8 isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid
  • Cyclohexanol
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.65 m3·mol-1ChemAxon
Polarizability51.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
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. [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. [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. [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
NuGOwiki LinkHMDB01438
Metagene LinkHMDB01438
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. [227368 ]