24,25-Dihydroxyvitamin D

Common Name

24,25-Dihydroxyvitamin D Description

24,25-Dihydroxyvitamin D (24R,25(OH)2D3) circliates in blood at concentrations about 1000 times higher than 1alpha,25(OH)2D3. 24-Hydroxylase is present in the proximal convoluted tublie cells of the kidney and in virtual all target cells of 1alpha,25(OH)2D3. Interestingly, 1alpha,25(OH)2D3 is a very strong inducer of 24-hydroxylase activity and 24R,25(OH)2D3 formation. Also parathyroid hormone (PTH) regliates 24-hydroxylase activity but in a tissue specific manner, i.e. inhibitory in the kidney while a synergistic effect together with 1alpha,25(OH)2D3 is observed in osteoblasts. Generally, 24-hydroxylation has been considered the first step in the degradation pathway of 1alpha,25(OH)2D3 and 25-(OH)D3. However, through the past decades data have accumliated that 24R,25(OH)2D3 is not merely a degradation product but has effects on its own. Classic studies have demonstrated the significance of 24R,25(OH)2D3 for normal chicken egg hatchability and calcium and phosphorus homeostasis. More recently it became apparent that 24R,25(OH)2D3 also has distinct effects on cartilage in particliar the resting zone cells. 24R,25(OH)2D3 stimliates osteocalcin synthesis in human osteoblasts. 24R,25(OH)2D3 plays a role in bone metabolism but that it acts in concert with 1alpha,25(OH)2D3 to obtain an optimal effect. (PMID: 11179746 ). Structure

Synonyms

Value Source (3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triolHMDB 24,25-DihydroxycholecalciferolHMDB 24,25-DihydroxyvitaminHMDB 24,25-Dihydroxyvitamin D3HMDB 24-HydroxycalcidiolHMDB Vitamin DHMDB 24,25 Dihydroxyvitamin D3MeSH (24R)-24,25-Dihydroxyvitamin D3MeSH 24,25-Dihydroxyvitamin D 3, (3beta,5Z,7E,24R)-isomerMeSH 24,25 DihydroxycholecalciferolMeSH Dihydroxyvitamin D3, 24,25MeSH 24R,25-DihydroxycholecalciferolMeSH 24,25 Dihydroxyvitamin D 3MeSH 24,25-Dihydroxyvitamin D 3MeSH

Chemical Formlia

C27H44O3 Average Molecliar Weight

416.6365 Monoisotopic Molecliar Weight

416.329045274 IUPAC Name

(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol Traditional Name

24,25-dihydroxyvitamin CAS Registry Number

40013-87-4 SMILES

C[C@H](CCC(O)C(C)(C)O)[C@H]1CC[C@@]2([H])C(CCC[C@]12C)=CC=C1C[C@H](O)CCC1=C

InChI Identifier

InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22-,23-,24+,25?,27-/m1/s1

InChI Key

FCKJYANJHNLEEP-OIMXRAFZSA-N Chemical Taxonomy Classification

Not classified 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 Emlisifiers
  • Cellliar locations

  • Extracellliar
  • Membrane (predicted from logP)
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0084 mg/mLALOGPS logP5.47ALOGPS logP4.58ChemAxon logS-4.7ALOGPS pKa (Strongest Acidic)13.85ChemAxon pKa (Strongest Basic)-1.3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area60.69 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity126.42 m3·mol-1ChemAxon Polarizability51.15 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane (predicted from logP)
  • Biofluid Locations

  • Blood
  • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.0043 +/- 0.0014 uMNewborn (0-30 days old)BothNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified0.0079 +/- 0.0031 uMChildren (1-13 years old)BothNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified0.005 +/- 0.0012 uMAdlit (>18 years old)BothNormal

  • Geigy Scientific …
  • details BloodDetected and Quantified0.0084 +/- 0.0033 uMAdlit (>18 years old)BothNormal

  • 227368
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.0045 +/- 0.0031 uMAdlit (>18 years old)MaleAnephrism

  • 227368
  • 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 Jli 15;182(1):55-69. [PubMed:227368 ]

    Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021793 KNApSAcK ID

    Not Available Chemspider ID

    17215953 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    vitamin D NuGOwiki Link

    HMDB00430 Metagene Link

    HMDB00430 METLIN ID

    5419 PubChem Compound

    12895043 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: MX69

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Ron M, Menczel J, Schwartz L, Palti Z, Kidroni G: Vitamin D3 metabolites in amniotic fluid in relation with maternal and fetal sera in term pregnancies. J Perinat Med. 1987;15(3):282-90. [PubMed:3501463 ]
    2. Imawari M, Kozawa K, Yoshida T, Osuga T: A simple and sensitive assay for 25-hydroxyvitamin D, 24,25-dihydroxyvitamin D and 1,25-dihydroxyvitamin D in human serum. Clin Chim Acta. 1982 Sep 1;124(1):63-73. [PubMed:6982126 ]
    3. Inaba M, Yukioka K, Furumitsu Y, Murano M, Goto H, Nishizawa Y, Morii H: Positive correlation between levels of IL-1 or IL-2 and 1,25(OH)2D/25-OH-D ratio in synovial fluid of patients with rheumatoid arthritis. Life Sci. 1997;61(10):977-85. [PubMed:9296336 ]
    4. Traba ML, Babe M, de la Piedra C, Marin A: 24,25-dihydroxyvitamin D3 in serum: sample purification with Sep-Pak C-18 cartridges and liquid chromatography before protein-binding assay. Clin Chem. 1983 Oct;29(10):1806-7. [PubMed:6604593 ]
    5. Coldwell RD, Trafford DJ, Makin HL, Varley MJ, Kirk DN: Specific estimation of 24,25-dihydroxyvitamin D in plasma by gas chromatography-mass spectrometry. Clin Chem. 1984 Jul;30(7):1193-8. [PubMed:6610503 ]
    6. Guillemant S, Kremer R: [Radiocompetitive estimation of 25-hydroxyvitamin D in human serum (authors transl)]. Ann Biol Clin (Paris). 1978;36(6):491-6. [PubMed:749564 ]
    7. Kumar R, Wiesner R, Scott M, Go VL: Physiology of 24,25-dihydroxyvitamin D3 in normal human subjects. Am J Physiol. 1982 Nov;243(5):E370-4. [PubMed:6753604 ]
    8. Lazebnik R, Eisenberg Z, Lazebnik N, Spirer Z, Weisman Y: Vitamin D metabolites in amniotic fluid. J Clin Endocrinol Metab. 1983 Mar;56(3):632-4. [PubMed:6600461 ]
    9. Mason RS, Lissner D, Grunstein HS, Posen S: A simplified assay for dihydroxylated vitamin D metabolites in human serum: application to hyper- and hypovitaminosis D. Clin Chem. 1980 Mar;26(3):444-50. [PubMed:6892691 ]
    10. van Leeuwen JP, van den Bemd GJ, van Driel M, Buurman CJ, Pols HA: 24,25-Dihydroxyvitamin D(3) and bone metabolism. Steroids. 2001 Mar-May;66(3-5):375-80. [PubMed:11179746 ]

    PMID: 927167