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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:39 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name24,25-Dihydroxyvitamin D
Description24,25-Dihydroxyvitamin D (24R,25(OH)2D3) circulates in blood at concentrations about 1000 times higher than 1alpha,25(OH)2D3. 24-Hydroxylase is present in the proximal convoluted tubule 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) regulates 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 accumulated 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 particular the resting zone cells. 24R,25(OH)2D3 stimulates 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 ).
24,25-Dihydroxyvitamin D3HMDB
Vitamin DHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
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 Name24,25-dihydroxyvitamin
CAS Registry Number40013-87-4
InChI Identifier
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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Steroid
  • Cyclohexanol
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0084 mg/mLALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.0043 +/- 0.0014 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.0079 +/- 0.0031 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.005 +/- 0.0012 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
BloodDetected and Quantified0.0084 +/- 0.0033 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.0045 +/- 0.0031 uMAdult (>18 years old)MaleAnephrism 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021793
KNApSAcK IDNot Available
Chemspider ID17215953
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkvitamin D
NuGOwiki LinkHMDB00430
Metagene LinkHMDB00430
PubChem Compound12895043
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot 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. [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. [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. [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. [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. [6610503 ]
  6. Guillemant S, Kremer R: [Radiocompetitive estimation of 25-hydroxyvitamin D in human serum (author's transl)] Ann Biol Clin (Paris). 1978;36(6):491-6. [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. [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. [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. [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. [11179746 ]