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Human Metabolome Database Version 3.5

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Showing metabocard for 25-Hydroxyvitamin D2 (HMDB01438)

Record Information
Version 3.5
Creation Date 2006-08-16 09:04:29 -0600
Update Date 2013-02-08 17:10:33 -0700
HMDB ID HMDB01438
Secondary Accession Numbers None
Metabolite Identification
Common Name 25-Hydroxyvitamin D2
Description 9,10-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 25-Hydroxycalciferol
  2. 25-Hydroxyergocalciferol
  3. 25-Hydroxyvitamin D
  4. 9,10-Secoergosta-5,7,10(19),22-tetraene-3b,25-diol
  5. Ercalcidiol
Chemical Formula C28H44O2
Average Molecular Weight 412.6478
Monoisotopic Molecular Weight 412.334130652
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 IUPAC Name (1S,3Z)-3-{2-[(3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
CAS Registry Number 21343-40-8
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 Key KJKIIUAXZGLUND-BJWBXCNSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Vitamin D and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Sesterterpenes
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
  • Tertiary Alcohol
Direct Parent Vitamin D and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.002 g/L ALOGPS
LogP 6.53 ALOGPS
LogP 5.66 ChemAxon
LogS -5.31 ALOGPS
pKa (strongest acidic) 18.38 ChemAxon
pKa (strongest basic) -0.85 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 130.65 ChemAxon
Polarizability 51.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.0023 +/- 0.00033 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.0097 (0.002-0.017) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.0032 (0.0022-0.0042) uM Adult (>18 years old) Both Normal After 1 week of high exposure to sun
Blood Detected and Quantified
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0.0085 +/- 0.0295 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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0.0879 +/- 0.023 uM Children (1-13 year old) Both Normal Not Available
Blood Detected and Quantified
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0.0347 +/- 0.0112 uM Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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0.000011 +/- 0.0000099 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.0037 +/- 0.0016 uM Adult (>18 years old) Both Smith-Lemli-Opitz syndrome Not Available
Blood Detected and Quantified
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0.046 (0.024-0.069) uM Adult (>18 years old) Both Anephrism Not Available
Urine Detected and Quantified
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0.0003 (0.000017-0.00065) umol/mmol creatinine Adult (>18 years old) Both Nephrotic syndrome Not Available
Associated Disorders and Diseases
Disease References
Anephric patients
  • 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 Link_out
    Smith-Lemli-Opitz syndrome
    • 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 Link_out
      Nephrotic syndrome
      • 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 Link_out
        Associated OMIM IDs
        • 270400 Link_out (Smith-Lemli-Opitz syndrome)
        DrugBank ID Not Available
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB022621
        KNApSAcK ID Not Available
        Chemspider ID 17216121 Link_out
        KEGG Compound ID Not Available
        BioCyc ID Not Available
        BiGG ID 2289188 Link_out
        Wikipedia Link Not Available
        NuGOwiki Link HMDB01438 Link_out
        Metagene Link HMDB01438 Link_out
        METLIN ID Not Available
        PubChem Compound 22833566 Link_out
        PDB ID Not Available
        ChEBI ID Not Available
        References
        Synthesis Reference Sardina, 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 Link_out