Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 23:33:54 UTC
Update Date2022-03-07 02:49:19 UTC
HMDB IDHMDB0003550
Secondary Accession Numbers
  • HMDB0005997
  • HMDB03550
  • HMDB05997
Metabolite Identification
Common NameCalcidiol
DescriptionCalcidiol, also known as 25(OH)D3 or rayaldee, 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. Thus, calcidiol is considered to be a secosteroid lipid molecule. Calcidiol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Calcidiol is a potentially toxic compound.
Structure
Data?1582752281
Synonyms
ValueSource
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
(3S,5Z,7E)-9,10-Secocholesta-5,7,10-triene-3,25-diolChEBI
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolChEBI
25(OH)D3ChEBI
25-HydroxycholecalciferolChEBI
25-Hydroxyvitamin D3ChEBI
3-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexanolChEBI
CalcifediolChEBI
Calcifediol anhydrousChEBI
CalcifediolumChEBI
RayaldeeChEBI
(3S,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-3,25-diolKegg
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diolGenerator
(3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diolGenerator
25-Hydroxy-cholecalciferolHMDB
5,6-cis-25-Hydroxyvitamin D3HMDB
9,10-Secocholesta-5,7,10(19)-triene-3b,25-diolHMDB
CalderolHMDB
DidrogylHMDB
HidroferolHMDB
25 Hydroxyvitamin D3HMDB
Calcifediol, (3 beta,5E,7E)-isomerHMDB
Monohydrate, 25-hydroxycholecalciferolHMDB
25-Hydroxycholecalciferol monohydrateHMDB
Anhydrous, calcifediolHMDB
Organon brand OF calcifediolHMDB
25 Hydroxyvitamin D 3HMDB
25-Hydroxyvitamin D 3HMDB
Aventis brand OF calcifediolHMDB
Calcifediol aventis brandHMDB
Calcifediol organon brandHMDB
DedrogylHMDB
25 HydroxycholecalciferolHMDB
25 Hydroxycholecalciferol monohydrateHMDB
Calcifediol faes brandHMDB
Calcifediol, (3 alpha,5Z,7E)-isomerHMDB
Faes brand OF calcifediolHMDB
CalcidiolMeSH
Chemical FormulaC27H44O2
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Name25-hydroxyvitamin D3
CAS Registry Number19356-17-3
SMILES
C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChI KeyJWUBBDSIWDLEOM-DTOXIADCSA-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
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available200.064http://allccs.zhulab.cn/database/detail?ID=AllCCS00000269
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP6.71ALOGPS
logP5.65ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.06 m³·mol⁻¹ChemAxon
Polarizability50.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.66831661259
DarkChem[M-H]-195.30831661259
DeepCCS[M-2H]-236.92330932474
DeepCCS[M+Na]+211.54230932474
AllCCS[M+H]+205.932859911
AllCCS[M+H-H2O]+203.732859911
AllCCS[M+NH4]+207.932859911
AllCCS[M+Na]+208.432859911
AllCCS[M-H]-205.232859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-209.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CalcidiolC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3361.7Standard polar33892256
CalcidiolC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3265.4Standard non polar33892256
CalcidiolC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3362.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Calcidiol,1TMS,isomer #1C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CCCC(C)(C)O[Si](C)(C)C3382.8Semi standard non polar33892256
Calcidiol,1TMS,isomer #2C=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)CCCC(C)(C)O3266.7Semi standard non polar33892256
Calcidiol,2TMS,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)CCCC(C)(C)O[Si](C)(C)C3361.3Semi standard non polar33892256
Calcidiol,1TBDMS,isomer #1C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)CCCC(C)(C)O[Si](C)(C)C(C)(C)C3612.5Semi standard non polar33892256
Calcidiol,1TBDMS,isomer #2C=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)CCCC(C)(C)O3467.1Semi standard non polar33892256
Calcidiol,2TBDMS,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)CCCC(C)(C)O[Si](C)(C)C(C)(C)C3829.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Calcidiol GC-MS (2 TMS)splash10-001i-2900000000-33a8e563016d6e2e358e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Calcidiol GC-MS (2 TMS)splash10-00lr-2900000000-f6bedf681276960630612014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Calcidiol GC-MS (Non-derivatized)splash10-001i-2900000000-33a8e563016d6e2e358e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Calcidiol GC-MS (Non-derivatized)splash10-00lr-2900000000-f6bedf681276960630612017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcidiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3029000000-4c75b5cfbc422ba2a3442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcidiol GC-MS (2 TMS) - 70eV, Positivesplash10-003r-1403290000-a8eb9294a6df1ce864d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcidiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calcidiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 10V, Positive-QTOFsplash10-00lr-0119100000-d3e0a5d2ecb614d781d42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 20V, Positive-QTOFsplash10-0api-0369000000-146e7a23795c22f5b8362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 40V, Positive-QTOFsplash10-0kai-5296000000-412b0c2da61c93271acd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 10V, Negative-QTOFsplash10-0002-0009000000-ef5150b1dccaed2f95432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 20V, Negative-QTOFsplash10-000t-0009000000-4b22b5c88dc06c01fe892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 40V, Negative-QTOFsplash10-00si-2229000000-f4037186ef5a21a168592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 10V, Negative-QTOFsplash10-0002-0009000000-21157f4aa99daf6972712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 20V, Negative-QTOFsplash10-0002-0009000000-cac0e3874faca9c17f032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 40V, Negative-QTOFsplash10-01ot-0339000000-37442d1a71c50883b3772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 10V, Positive-QTOFsplash10-001i-0549100000-68f99126c8d8b4ca7eb72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 20V, Positive-QTOFsplash10-0g4i-5594100000-433f2a913eb577e9397a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calcidiol 40V, Positive-QTOFsplash10-0ab9-1940000000-e03ff70cb44513aa8ae82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Epidermis
  • Kidney
  • Ovary
  • Prostate
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0422 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.035 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0300-0.155 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified0.042 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.044 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0547 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0689 (0.0459-0.0919) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.057 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0634 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.13 (0.13-0.14) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.064 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.074 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.08 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.081 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0577 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0600 +/- 0.0222 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0678 +/- 0.0222 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0469 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0600 +/- 0.0146 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.07 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.078 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0831 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0700 +/- 0.0310 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0730 +/- 0.0310 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.095 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.108 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0790 +/- 0.0340 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0830 +/- 0.0320 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.0245 +/- 0.023 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified>0.0749 uMNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.092 +/- 0.0037 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0137 uMInfant (0-1 year old)FemalePyroglutamic aciduria details
BloodDetected and Quantified0.044 (0.013-0.074) uMAdult (>18 years old)BothAnephrism details
BloodDetected and Quantified0.0549 +/- 0.0225 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0449 +/- 0.00749 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0599 +/- 0.0200 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0704 uMAdult (>18 years old)Male
Bartter Syndrome, Type 4A, Neonatal, with Sensorineural Deafness
details
UrineDetected and Quantified0.0099 +/- 0.0019 umol/mmol creatinineAdult (>18 years old)BothNephrotic syndrome 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 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ]
Bartter Syndrome, Type 4A, Neonatal, with Sensorineural Deafness
  1. Heilberg IP, Totoli C, Calado JT: Adult presentation of Bartter syndrome type IV with erythrocytosis. Einstein (Sao Paulo). 2015 Oct-Dec;13(4):604-6. doi: 10.1590/S1679-45082015RC3013. Epub 2015 Oct 30. [PubMed:26537508 ]
Nephrotic syndrome
  1. Goldstein DA, Haldimann B, Sherman D, Norman AW, Massry SG: Vitamin D metabolites and calcium metabolism in patients with nephrotic syndrome and normal renal function. J Clin Endocrinol Metab. 1981 Jan;52(1):116-21. [PubMed:6969729 ]
Associated OMIM IDs
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 602522 (Bartter Syndrome, Type 4A, Neonatal, with Sensorineural Deafness)
DrugBank IDDB00146
Phenol Explorer Compound IDNot Available
FooDB IDFDB021782
KNApSAcK IDC00040805
Chemspider ID4446820
KEGG Compound IDC01561
BioCyc IDNot Available
BiGG ID2289142
Wikipedia LinkCalcifediol
METLIN ID6949
PubChem Compound5283731
PDB IDNot Available
ChEBI ID17933
Food Biomarker OntologyNot Available
VMH ID25HVITD3
MarkerDB IDMDB00000426
Good Scents IDNot Available
References
Synthesis ReferenceMascarenas, J. L.; Mourino, A.; Castedo, L. Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 3. Synthesis of 25-ketovitamin D3 and 25-hydroxyvitamin D3. Journal of Organic Chemistry (1986), 51(8), 1269-72.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72. [PubMed:16886665 ]
  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 ]
  3. Passadakis P, Ersoy F, Tam P, Memmos D, Siamopoulos K, Ozener C, Akcicek F, Camsari T, Ates K, Ataman R, Vlachojannis J, Dombros N, Utas C, Akpolat T, Bozfakioglu S, Wu GG, Karayaylali I, Arinsoy T, Stathakis C, Yavuz M, Tsakiris D, Dimitriades A, Yilmaz ME, Gultekin M, Karayalcin B, Challa A, Polat N, Oreopoulos DG: Serum levels of prostate-specific antigen and vitamin D in peritoneal dialysis patients. Adv Perit Dial. 2004;20:203-8. [PubMed:15384827 ]
  4. Park SB, Suh DH, Youn JI: A pilot study to assess the safety and efficacy of topical calcipotriol treatment in childhood psoriasis. Pediatr Dermatol. 1999 Jul-Aug;16(4):321-5. [PubMed:10469423 ]
  5. Haden ST, Fuleihan GE, Angell JE, Cotran NM, LeBoff MS: Calcidiol and PTH levels in women attending an osteoporosis program. Calcif Tissue Int. 1999 Apr;64(4):275-9. [PubMed:10089217 ]
  6. Gacad MA, Adams JS: Proteins in the heat shock-70 family specifically bind 25-hydroxyvitamin D3 and 17beta-estradiol. J Clin Endocrinol Metab. 1998 Apr;83(4):1264-7. [PubMed:9543154 ]
  7. Feingold KR, Williams ML, Pillai S, Menon GK, Halloran BP, Bikle DD, Elias PM: The effect of vitamin D status on cutaneous sterologenesis in vivo and in vitro. Biochim Biophys Acta. 1987 Sep 14;930(2):193-200. [PubMed:3040120 ]
  8. 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 ]
  9. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

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
Reactions
Calcidiol + NADPH + Oxygen → Calcitriol + NADP + Waterdetails
Calcidiol + Oxygen + NADPH + Hydrogen Ion → Calcitriol + NADP + Waterdetails
References
  1. Schuster I: Cytochromes P450 are essential players in the vitamin D signaling system. Biochim Biophys Acta. 2011 Jan;1814(1):186-99. doi: 10.1016/j.bbapap.2010.06.022. Epub 2010 Jul 7. [PubMed:20619365 ]
  2. Bernad M, Jaramillo G, Aguado P, del Campo T, Coya J, Martin Mola E, Gijon Banos J, Saldana Barrera H, Martinez ME: [Polymorphism of the gene of vitamin D receptor and bone mineral density in postmenopausal women]. Med Clin (Barc). 1999 May 15;112(17):651-5. [PubMed:10374186 ]
  3. Diesel B, Radermacher J, Bureik M, Bernhardt R, Seifert M, Reichrath J, Fischer U, Meese E: Vitamin D(3) metabolism in human glioblastoma multiforme: functionality of CYP27B1 splice variants, metabolism of calcidiol, and effect of calcitriol. Clin Cancer Res. 2005 Aug 1;11(15):5370-80. [PubMed:16061850 ]
  4. Eto TA, Nakamura Y, Taniguchi T, Miyamoto K, Nagatomo J, Maeda Y, Higashi S, Okuda K, Setoguchi T: Assay of 25-hydroxyvitamin D3 1 alpha-hydroxylase in rat kidney mitochondria. Anal Biochem. 1998 Apr 10;258(1):53-8. [PubMed:9527847 ]
  5. Hart GR, Furniss JL, Laurie D, Durham SK: Measurement of vitamin D status: background, clinical use, and methodologies. Clin Lab. 2006;52(7-8):335-43. [PubMed:16955631 ]
  6. Vigo Gago E, Cadarso-Suarez C, Perez-Fernandez R, Romero Burgos R, Devesa Mugica J, Segura Iglesias C: Association between vitamin D receptor FokI. Polymorphism and serum parathyroid hormone level in patients with chronic renal failure. J Endocrinol Invest. 2005 Feb;28(2):117-21. [PubMed:15887856 ]
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. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [PubMed:15503649 ]
  2. 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
Reactions
Calcidiol + NADPH + Oxygen → (24R)-24,25-Dihydroxycalciol + NADP + Waterdetails
Calcidiol + NADPH + Hydrogen Ion + Oxygen → Secalciferol + NADP + Waterdetails
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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
Reactions
Vitamin D3 + Oxygen + NADPH → Calcidiol + NADP(+) H(2)Odetails
Calcidiol + NADP + Water → Vitamin D3 + NADPH + Hydrogen Ion + Oxygendetails