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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:07 UTC
HMDB IDHMDB0000900
Secondary Accession Numbers
  • HMDB00900
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
Data?1582752163
Synonyms
ValueSource
(3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
Activated ergosterolChEBI
CalciferolChEBI
ErcalciolChEBI
ErgocalciferolumChEBI
Oleovitamin D2ChEBI
ViosterolChEBI
Vitamina D2ChEBI
Vitamin D2Kegg
DrisdolKegg
(3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(+)-Vitamin D2HMDB
(5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-olHMDB
22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-olHMDB
4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanolHMDB
9,10-Secoergosta-5,7,10(19),22-tetraen-3b-olHMDB
beta-OlHMDB
Buco-DHMDB
Calciferon 2HMDB
CondacapsHMDB
CondocapsHMDB
CondolHMDB
CrtronHMDB
CrystallinaHMDB
D-ArthinHMDB
D-TracettenHMDB
DaralHMDB
Davitamon DHMDB
DavitinHMDB
De-rat concentrateHMDB
DecapsHMDB
Dee-osterolHMDB
Dee-ronHMDB
Dee-ronalHMDB
Dee-roualHMDB
delta-ArthinHMDB
delta-TracettenHMDB
DeltalinHMDB
DeratolHMDB
DetalupHMDB
DiactolHMDB
Divit urtoHMDB
DoralHMDB
Ergocalciferol oilHMDB
ErgoroneHMDB
Ergosterol activatedHMDB
Ergosterol irradiatedHMDB
ErtronHMDB
FortodylHMDB
GeltabsHMDB
Hi-deratolHMDB
InfronHMDB
Irradiated ergosta-5,7,22-trien-3beta-olHMDB
MetadeeHMDB
Mina D2HMDB
MulsiferolHMDB
MykostinHMDB
Novovitamin-DHMDB
Oleovitamin DHMDB
OsteilHMDB
OstelinHMDB
RadiostolHMDB
RadsteinHMDB
RadsterinHMDB
Rodine CHMDB
Shock-ferolHMDB
Shock-ferol sterogylHMDB
SterogylHMDB
Synthetic vitamin DHMDB
Uvesterol DHMDB
Uvesterol-DHMDB
Vio DHMDB
Vio-DHMDB
ViostdrolHMDB
Viosterol in oilHMDB
Vitavel-DHMDB
CalciferolsHMDB
ErgocalciferolsHMDB
D2, VitaminHMDB
Vitamin D 2HMDB
ErgocalciferolChEBI
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 Nameergocalciferol
CAS Registry Number50-14-6
SMILES
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)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
Description Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.05 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available203.385http://allccs.zhulab.cn/database/detail?ID=AllCCS00000448
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00043 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 Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.89 m³·mol⁻¹ChemAxon
Polarizability50.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.11231661259
DarkChem[M-H]-197.26931661259
AllCCS[M+H]+205.45632859911
AllCCS[M-H]-206.25832859911
DeepCCS[M-2H]-240.06830932474
DeepCCS[M+Na]+214.94530932474
AllCCS[M+H]+205.532859911
AllCCS[M+H-H2O]+203.232859911
AllCCS[M+NH4]+207.532859911
AllCCS[M+Na]+208.132859911
AllCCS[M-H]-206.332859911
AllCCS[M+Na-2H]-208.232859911
AllCCS[M+HCOO]-210.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ergocalciferol[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C3557.3Standard polar33892256
Ergocalciferol[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C3172.7Standard non polar33892256
Ergocalciferol[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C3268.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ergocalciferol,1TMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)/C=C/[C@H](C)C(C)C3199.8Semi standard non polar33892256
Ergocalciferol,1TBDMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)/C=C/[C@H](C)C(C)C3431.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ergocalciferol GC-MS (1 TMS)splash10-003u-3911000000-dba9e396497310b317152014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ergocalciferol GC-MS (Non-derivatized)splash10-003u-3911000000-dba9e396497310b317152017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergocalciferol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-3019000000-8a847f6179b3a364ad052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergocalciferol GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-4103900000-4c6f376ae6706d7e85562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergocalciferol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergocalciferol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergocalciferol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-0129000000-77bd32807ec8ea97183b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergocalciferol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0601-5902000000-ae4a4363ac10f9f0feb72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergocalciferol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05mo-9800000000-1ea9f4fa17117a9e65152012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergocalciferol LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-01ot-9801000000-17d2120d47f9c718ea952012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergocalciferol LC-ESI-QTOF , positive-QTOFsplash10-01ot-9801000000-c10341d61ee2d63692192017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 10V, Positive-QTOFsplash10-004j-1129000000-41a3f60b47798eb6bd6c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 20V, Positive-QTOFsplash10-05ai-4694000000-95577608302dfef840b42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 40V, Positive-QTOFsplash10-0gx9-9464000000-f7bcbdb6e805513cd6612017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 10V, Negative-QTOFsplash10-0002-0009000000-819b52cfd84baf07f5502017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 20V, Negative-QTOFsplash10-0002-0009000000-5ed8b1f535a88d73555c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 40V, Negative-QTOFsplash10-004i-3249000000-bf201c27d3bc67289adb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 10V, Positive-QTOFsplash10-006t-0398000000-dfcffd595ce9725ef52c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 20V, Positive-QTOFsplash10-0uk9-4192000000-c93d9259f7db1789c50a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 40V, Positive-QTOFsplash10-015c-9340000000-aa858d8ca84ec1673a552021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 10V, Negative-QTOFsplash10-0002-0009000000-2f6aa9af0bd8878fb6c62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 20V, Negative-QTOFsplash10-002b-0109000000-7977d6caa249a0925fb32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergocalciferol 40V, Negative-QTOFsplash10-0006-1759000000-2c5dd594802c53ac80a12021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.003 (0.000-0.007) uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0025 (0.0008-0.0042) uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified0.008 +/- 0.002 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0032 (0.0017-0.0047) 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. [PubMed:227368 ]
Associated OMIM IDsNone
DrugBank IDDB00153
Phenol Explorer Compound IDNot Available
FooDB IDFDB012811
KNApSAcK IDNot Available
Chemspider ID4444351
KEGG Compound IDC05441
BioCyc IDVITAMIN_D2
BiGG ID2289183
Wikipedia LinkErgocalciferol
METLIN ID5856
PubChem Compound5280793
PDB IDNot Available
ChEBI ID28934
Food Biomarker OntologyNot Available
VMH IDVITD2
MarkerDB IDNot Available
Good Scents IDNot Available
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, Gies 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

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
References
  1. Binkley N, Ramamurthy R, Krueger D: Low vitamin D status: definition, prevalence, consequences, and correction. Endocrinol Metab Clin North Am. 2010 Jun;39(2):287-301, table of contents. doi: 10.1016/j.ecl.2010.02.008. [PubMed:20511052 ]
  2. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  4. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712 ]
  5. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
Gene Name:
CYP27B1
Uniprot ID:
O15528
Molecular weight:
56503.475
References
  1. Turunen MM, Dunlop TW, Carlberg C, Vaisanen S: Selective use of multiple vitamin D response elements underlies the 1 alpha,25-dihydroxyvitamin D3-mediated negative regulation of the human CYP27B1 gene. Nucleic Acids Res. 2007;35(8):2734-47. Epub 2007 Apr 10. [PubMed:17426122 ]
  2. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913 ]
  3. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Regulates transcription of hormone sensitive genes via its association with the WINAC complex, a chromatin-remodeling complex. Recruited to promoters via its interaction with the WINAC complex subunit BAZ1B/WSTF, which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis
Gene Name:
VDR
Uniprot ID:
P11473
Molecular weight:
48288.6
References
  1. Carvallo L, Henriquez B, Olate J, van Wijnen AJ, Lian JB, Stein GS, Onate S, Stein JL, Montecino M: The 1alpha,25-dihydroxy Vitamin D3 receptor preferentially recruits the coactivator SRC-1 during up-regulation of the osteocalcin gene. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):420-4. Epub 2007 Jan 10. [PubMed:17218095 ]
  2. Liu W, Tretiakova M, Kong J, Turkyilmaz M, Li YC, Krausz T: Expression of vitamin D3 receptor in kidney tumors. Hum Pathol. 2006 Oct;37(10):1268-78. Epub 2006 Jul 27. [PubMed:16949927 ]
  3. Ewing AK, Attner M, Chakravarti D: Novel regulatory role for human Acf1 in transcriptional repression of vitamin D3 receptor-regulated genes. Mol Endocrinol. 2007 Aug;21(8):1791-806. Epub 2007 May 22. [PubMed:17519354 ]
  4. Gallagher JC, Sai AJ: Vitamin D insufficiency, deficiency, and bone health. J Clin Endocrinol Metab. 2010 Jun;95(6):2630-3. doi: 10.1210/jc.2010-0918. [PubMed:20525913 ]
  5. Straube S, Derry S, Moore RA, McQuay HJ: Vitamin D for the treatment of chronic painful conditions in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD007771. doi: 10.1002/14651858.CD007771.pub2. [PubMed:20091647 ]
  6. Jurutka PW, Bartik L, Whitfield GK, Mathern DR, Barthel TK, Gurevich M, Hsieh JC, Kaczmarska M, Haussler CA, Haussler MR: Vitamin D receptor: key roles in bone mineral pathophysiology, molecular mechanism of action, and novel nutritional ligands. J Bone Miner Res. 2007 Dec;22 Suppl 2:V2-10. doi: 10.1359/jbmr.07s216. [PubMed:18290715 ]
  7. Mikhak B, Hunter DJ, Spiegelman D, Platz EA, Hollis BW, Giovannucci E: Vitamin D receptor (VDR) gene polymorphisms and haplotypes, interactions with plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D, and prostate cancer risk. Prostate. 2007 Jun 15;67(9):911-23. [PubMed:17440943 ]
  8. Marks HD, Fleet JC, Peleg S: Transgenic expression of the human Vitamin D receptor (hVDR) in the duodenum of VDR-null mice attenuates the age-dependent decline in calcium absorption. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):513-6. Epub 2007 Jan 5. [PubMed:17207992 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Has a role in maintaining calcium homeostasis. Catalyzes the NADPH-dependent 24-hydroxylation of calcidiol (25-hydroxyvitamin D(3)) and calcitriol (1-alpha,25-dihydroxyvitamin D(3)). The enzyme can perform up to 6 rounds of hydroxylation of calcitriol leading to calcitroic acid. It also shows 23-hydroxylating activity leading to 1-alpha,25-dihydroxyvitamin D(3)-26,23-lactone as end product.
Gene Name:
CYP24A1
Uniprot ID:
Q07973
Molecular weight:
58874.695
References
  1. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
  2. Sakaki T, Kagawa N, Yamamoto K, Inouye K: Metabolism of vitamin D3 by cytochromes P450. Front Biosci. 2005 Jan 1;10:119-34. Print 2005 Jan 1. [PubMed:15574355 ]
  3. Abe D, Sakaki T, Kusudo T, Kittaka A, Saito N, Suhara Y, Fujishima T, Takayama H, Hamamoto H, Kamakura M, Ohta M, Inouye K: Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1. Drug Metab Dispos. 2005 Jun;33(6):778-84. Epub 2005 Mar 11. [PubMed:15764712 ]
  4. Sakaki T: [Recent studies on vitamin D metabolizing enzymes]. Clin Calcium. 2006 Jul;16(7):1129-35. [PubMed:16816472 ]
  5. Inouye K, Sakaki T: Enzymatic studies on the key enzymes of vitamin D metabolism; 1 alpha-hydroxylase (CYP27B1) and 24-hydroxylase (CYP24). Biotechnol Annu Rev. 2001;7:179-94. [PubMed:11686044 ]
General function:
Involved in monooxygenase activity
Specific function:
Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3).
Gene Name:
CYP2R1
Uniprot ID:
Q6VVX0
Molecular weight:
57358.82
References
  1. Ramos-Lopez E, Bruck P, Jansen T, Pfeilschifter JM, Radeke HH, Badenhoop K: CYP2R1-, CYP27B1- and CYP24-mRNA expression in German type 1 diabetes patients. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):807-10. Epub 2007 Jan 16. [PubMed:17223345 ]
  2. Ramos-Lopez E, Bruck P, Jansen T, Herwig J, Badenhoop K: CYP2R1 (vitamin D 25-hydroxylase) gene is associated with susceptibility to type 1 diabetes and vitamin D levels in Germans. Diabetes Metab Res Rev. 2007 Nov;23(8):631-6. [PubMed:17607662 ]
  3. Masuda S, Strugnell SA, Knutson JC, St-Arnaud R, Jones G: Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2. Biochim Biophys Acta. 2006 Feb;1761(2):221-34. Epub 2006 Feb 2. [PubMed:16516540 ]
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
General function:
Involved in thymidylate kinase activity
Specific function:
May participate in dUTP and dCTP synthesis in mitochondria. Is able to phosphorylate dUMP, dCMP, CMP, UMP and monophosphates of the pyrimidine nucleoside analogs ddC, dFdC, araC, BVDU and FdUrd with ATP as phosphate donor. Efficacy is highest for dUMP followed by dCMP; CMP and UMP are poor substrates. May be involved in mtDNA depletion caused by long term treatment with ddC or other pyrimidine analogs.
Gene Name:
CMPK2
Uniprot ID:
Q5EBM0
Molecular weight:
44958.27
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase (By similarity).
Gene Name:
NT5C3L
Uniprot ID:
Q969T7
Molecular weight:
Not Available