Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:33 UTC
HMDB IDHMDB00900
Secondary Accession NumbersNone
Metabolite Identification
Common NameErgocalciferol
DescriptionErgocalciferol is a form of Vitamin D, also called vitamin D2. It is created from viosterol, which in turn is created when ultraviolet light activates ergosterol. Ergocalciferol is used in the treatment of hypcalcemia and in dialysis-dependent renal failure. Ergoalcifediol is a fat soluble steroid hormone precursor of vitamin D that contributes to the maintenance of normal levels of calcium and phosphorus in the bloodstream. Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles.
Structure
Thumb
Synonyms
  1. (+)-Vitamin D2
  2. (5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-ol
  3. 22-Tetraen 3beta 9,10,Secoergosta-5,7,10(19)-ol
  4. 4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3aH)-indanylidene]ethylidene]-Cyclohexanol
  5. 9,10-Secoergosta-5,7,10(19),22-tetraen-3b-ol
  6. beta-Ol
  7. Buco-D
  8. Calciferol
  9. Calciferon 2
  10. Condacaps
  11. Condocaps
  12. Condol
  13. Crtron
  14. Crystallina
  15. D-Arthin
  16. D-Tracetten
  17. Daral
  18. Davitamon D
  19. Davitin
  20. De-rat concentrate
  21. Decaps
  22. Dee-Osterol
  23. Dee-Ron
  24. Dee-Ronal
  25. Dee-Roual
  26. delta-Arthin
  27. delta-Tracetten
  28. Deltalin
  29. Deratol
  30. Detalup
  31. Diactol
  32. Divit urto
  33. Doral
  34. Drisdol
  35. Ercalciol
  36. Ergocalciferol
  37. Ergocalciferol oil
  38. Ergorone
  39. Ergosterol activated
  40. Ergosterol irradiated
  41. Ertron
  42. Fortodyl
  43. Geltabs
  44. Hi-Deratol
  45. Infron
  46. Irradiated ergosta-5,7,22-trien-3beta-ol
  47. Metadee
  48. Mina D2
  49. Mulsiferol
  50. Mykostin
  51. Novovitamin-D
  52. Oleovitamin D
  53. Oleovitamin D2
  54. Osteil
  55. Ostelin
  56. Radiostol
  57. Radstein
  58. Radsterin
  59. Rodine C
  60. Shock-ferol
  61. Shock-ferol sterogyl
  62. Sterogyl
  63. Synthetic Vitamin D
  64. Uvesterol D
  65. Uvesterol-D
  66. Vio D
  67. Vio-D
  68. Viostdrol
  69. Viosterol
  70. Viosterol in Oil
  71. Vitamin D2
  72. Vitavel-D
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional IUPAC Nameergocalciferol
CAS Registry Number50-14-6
SMILES
CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
InChI KeyMECHNRXZTMCUDQ-RKHKHRCZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassVitamin D and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Sesterterpenes
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Secondary Alcohol
Direct ParentVitamin D and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Essential vitamins
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point116.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.05 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.330E-04 g/LALOGPS
logP7.59ALOGPS
logP7.05ChemAxon
logS-6ALOGPS
pKa (strongest acidic)18.38ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count5ChemAxon
refractivity128.89ChemAxon
polarizability50.75ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Bladder
  • Brain
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Nerve Cells
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.003 (0.000-0.007) uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified0.0025 (0.0008-0.0042) uMAdult (>18 years old)MaleCommentNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0032 (0.0017-0.0047) uMAdult (>18 years old)MaleAnephrism
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
Associated OMIM IDsNone
DrugBank IDDB00153
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012811
KNApSAcK IDNot Available
Chemspider ID4444351
KEGG Compound IDC05441
BioCyc IDVITAMIN_D_{2}
BiGG ID2289183
Wikipedia LinkErgocalciferol
NuGOwiki LinkHMDB00900
Metagene LinkHMDB00900
METLIN ID5856
PubChem Compound5280793
PDB IDD2V
ChEBI ID28934
References
Synthesis ReferenceOkabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.
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
  2. Samanek AJ, Croager EJ, Giesfor Skin Cancer Prevention P, Milne E, Prince R, McMichael AJ, Lucas RM, Slevin T: Estimates of beneficial and harmful sun exposure times during the year for major Australian population centres. Med J Aust. 2006 Apr 3;184(7):338-41. Pubmed: 16584368
  3. Bischoff HA, Borchers M, Gudat F, Duermueller U, Theiler R, Stahelin HB, Dick W: In situ detection of 1,25-dihydroxyvitamin D3 receptor in human skeletal muscle tissue. Histochem J. 2001 Jan;33(1):19-24. Pubmed: 11352397
  4. Jorde R, Saleh F, Figenschau Y, Kamycheva E, Haug E, Sundsfjord J: Serum parathyroid hormone (PTH) levels in smokers and non-smokers. The fifth Tromso study. Eur J Endocrinol. 2005 Jan;152(1):39-45. Pubmed: 15762185
  5. Bischoff-Ferrari HA, Borchers M, Gudat F, Durmuller U, Stahelin HB, Dick W: Vitamin D receptor expression in human muscle tissue decreases with age. J Bone Miner Res. 2004 Feb;19(2):265-9. Pubmed: 14969396
  6. Young MV, Schwartz GG, Wang L, Jamieson DP, Whitlatch LW, Flanagan JN, Lokeshwar BL, Holick MF, Chen TC: The prostate 25-hydroxyvitamin D-1 alpha-hydroxylase is not influenced by parathyroid hormone and calcium: implications for prostate cancer chemoprevention by vitamin D. Carcinogenesis. 2004 Jun;25(6):967-71. Epub 2004 Jan 16. Pubmed: 14729578
  7. Jones G, Strugnell SA, DeLuca HF: Current understanding of the molecular actions of vitamin D. Physiol Rev. 1998 Oct;78(4):1193-231. Pubmed: 9790574
  8. Langman CB, Brooks ER: Renal osteodystrophy in children: a systemic disease associated with cardiovascular manifestations. Growth Horm IGF Res. 2006 Jul;16 Suppl A:S79-83. Epub 2006 Apr 18. Pubmed: 16624609
  9. Reginster JY: The high prevalence of inadequate serum vitamin D levels and implications for bone health. Curr Med Res Opin. 2005 Apr;21(4):579-86. Pubmed: 15899107
  10. Tuohimaa P, Tenkanen L, Ahonen M, Lumme S, Jellum E, Hallmans G, Stattin P, Harvei S, Hakulinen T, Luostarinen T, Dillner J, Lehtinen M, Hakama M: Both high and low levels of blood vitamin D are associated with a higher prostate cancer risk: a longitudinal, nested case-control study in the Nordic countries. Int J Cancer. 2004 Jan 1;108(1):104-8. Pubmed: 14618623
  11. Malloy PJ, Xu R, Peng L, Clark PA, Feldman D: A novel mutation in helix 12 of the vitamin D receptor impairs coactivator interaction and causes hereditary 1,25-dihydroxyvitamin D-resistant rickets without alopecia. Mol Endocrinol. 2002 Nov;16(11):2538-46. Pubmed: 12403843
  12. Boyle MP, Noschese ML, Watts SL, Davis ME, Stenner SE, Lechtzin N: Failure of high-dose ergocalciferol to correct vitamin D deficiency in adults with cystic fibrosis. Am J Respir Crit Care Med. 2005 Jul 15;172(2):212-7. Epub 2005 Apr 28. Pubmed: 15860755
  13. Salle BL, Delvin EE, Lapillonne A, Bishop NJ, Glorieux FH: Perinatal metabolism of vitamin D. Am J Clin Nutr. 2000 May;71(5 Suppl):1317S-24S. Pubmed: 10799409
  14. Bai S, Favus MJ: Vitamin D and calcium receptors: links to hypercalciuria. Curr Opin Nephrol Hypertens. 2006 Jul;15(4):381-5. Pubmed: 16775452
  15. Vieth R: The role of vitamin D in the prevention of osteoporosis. Ann Med. 2005;37(4):278-85. Pubmed: 16019727
  16. Robinson DM, Scott LJ: Spotlight on paricalcitol in secondary hyperparathyroidism. Treat Endocrinol. 2005;4(3):185-6. Pubmed: 15898824
  17. Bouillon R, Verstuyf A, Zhao J, Tan BK, Van Baelen H: Nonhypercalcemic vitamin D analogs: interactions with the vitamin D-binding protein. Horm Res. 1996;45(3-5):117-21. Pubmed: 8964569
  18. Moreira RO, Duarte MP, Farias ML: [Disturbances of calcium-PTH-vitamin D axis in chronic liver diseases] Arq Bras Endocrinol Metabol. 2004 Aug;48(4):443-50. Epub 2005 Mar 7. Pubmed: 15761507
  19. Shah N, Bernardini J, Piraino B: Prevalence and correction of 25(OH) vitamin D deficiency in peritoneal dialysis patients. Perit Dial Int. 2005 Jul-Aug;25(4):362-6. Pubmed: 16022093
  20. Makishima M, Lu TT, Xie W, Whitfield GK, Domoto H, Evans RM, Haussler MR, Mangelsdorf DJ: Vitamin D receptor as an intestinal bile acid sensor. Science. 2002 May 17;296(5571):1313-6. Pubmed: 12016314
  21. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. Pubmed: 15585789

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Gene Name:
VDR
Uniprot ID:
P11473
Gene Name:
CYP2R1
Uniprot ID:
Q6VVX0
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Gene Name:
CMPK2
Uniprot ID:
Q5EBM0