Human Metabolome Database Version 3.5

Showing metabocard for Ergocalciferol (HMDB00900)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:33 -0700
HMDB ID HMDB00900
Secondary Accession Numbers None
Metabolite Identification
Common Name Ergocalciferol
Description Ergocalciferol 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C28H44O
Average Molecular Weight 396.6484
Monoisotopic Molecular Weight 396.33921603
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 Name ergocalciferol
CAS Registry Number 50-14-6
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 Key MECHNRXZTMCUDQ-RKHKHRCZSA-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
Direct Parent Vitamin D and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 116.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.05 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.330E-04 g/L ALOGPS
LogP 7.59 ALOGPS
LogP 7.05 ChemAxon
LogS -5.96 ALOGPS
pKa (strongest acidic) 18.38 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 128.89 ChemAxon
Polarizability 50.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Pancreas
  • Placenta
  • Kidney
  • Liver
  • Brain
  • Prostate
  • Skin
  • Adipose Tissue
  • Nerve Cells
  • Gonads
  • Spleen
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.003 (0.000-0.007) uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
0.0025 (0.0008-0.0042) uM Adult (>18 years old) Male Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0032 (0.0017-0.0047) uM Adult (>18 years old) Male Anephrism
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
      Associated OMIM IDs None
      DrugBank ID DB00153 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012811
      KNApSAcK ID Not Available
      Chemspider ID 4444351 Link_out
      KEGG Compound ID C05441 Link_out
      BioCyc ID VITAMIN_D_{2} Link_out
      BiGG ID 2289183 Link_out
      Wikipedia Link Ergocalciferol Link_out
      NuGOwiki Link HMDB00900 Link_out
      Metagene Link HMDB00900 Link_out
      METLIN ID 5856 Link_out
      PubChem Compound 5280793 Link_out
      PDB ID D2V Link_out
      ChEBI ID 28934 Link_out
      References
      Synthesis Reference Okabe, 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. 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 Link_out
      2. 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
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      15. Vieth R: The role of vitamin D in the prevention of osteoporosis. Ann Med. 2005;37(4):278-85. Pubmed: 16019727 Link_out
      16. Robinson DM, Scott LJ: Spotlight on paricalcitol in secondary hyperparathyroidism. Treat Endocrinol. 2005;4(3):185-6. Pubmed: 15898824 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Cytochrome P450 3A4
      Reactions: Not Available
      Gene Name: CYP3A4
      Uniprot ID: P08684 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sterol 26-hydroxylase, mitochondrial
      Reactions: Not Available
      Gene Name: CYP27A1
      Uniprot ID: Q02318 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial
      Reactions: Not Available
      Gene Name: CYP27B1
      Uniprot ID: O15528 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Vitamin D3 receptor
      Reactions: Not Available
      Gene Name: VDR
      Uniprot ID: P11473 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial
      Reactions: Not Available
      Gene Name: CYP24A1
      Uniprot ID: Q07973 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Vitamin D 25-hydroxylase
      Reactions: Not Available
      Gene Name: CYP2R1
      Uniprot ID: Q6VVX0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase 3
      Reactions: Not Available
      Gene Name: NT5C3
      Uniprot ID: Q9H0P0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: UMP-CMP kinase 2, mitochondrial
      Reactions: Not Available
      Gene Name: CMPK2
      Uniprot ID: Q5EBM0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytosolic 5'-nucleotidase III-like protein
      Reactions: Not Available
      Gene Name: NT5C3L
      Uniprot ID: Q969T7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA