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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-16 15:04:29 UTC
Update Date2022-03-07 02:49:09 UTC
HMDB IDHMDB0001438
Secondary Accession Numbers
  • HMDB01438
Metabolite Identification
Common Name25-Hydroxyvitamin D2
Description25-Hydroxyvitamin D2, also known as 25-hydroxycalciferol or ercalcidiol, 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. Based on a literature review very few articles have been published on 25-Hydroxyvitamin D2.
Structure
Data?1582752201
Synonyms
ValueSource
25-HydroxycalciferolHMDB
25-HydroxyergocalciferolHMDB
25-Hydroxyvitamin DHMDB
9,10-Secoergosta-5,7,10(19),22-tetraene-3b,25-diolHMDB
ErcalcidiolHMDB
25 HydroxycalciferolHMDB
9,10-Secoergosta-5,7,10(19),22-tetraene-3 beta,25-diolHMDB
25 Hydroxyvitamin D2HMDB
25-Hydroxyvitamin D 2HMDB
25 Hydroxyvitamin D 2HMDB
25 HydroxyergocalciferolHMDB
25-Hydroxyvitamin D2MeSH
Chemical FormulaC28H44O2
Average Molecular Weight412.6478
Monoisotopic Molecular Weight412.334130652
IUPAC Name(1S,3Z)-3-{2-[(3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Name25-hydroxyvitamin D
CAS Registry Number21343-40-8
SMILES
C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI Identifier
InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/b11-9+,22-12+,23-13-/t20-,21+,24+,25?,26+,28-/m1/s1
InChI KeyKJKIIUAXZGLUND-BJWBXCNSSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP6.53ALOGPS
logP5.66ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.65 m³·mol⁻¹ChemAxon
Polarizability51.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.08831661259
DarkChem[M-H]-197.90631661259
AllCCS[M+H]+207.50732859911
AllCCS[M-H]-208.04932859911
DeepCCS[M-2H]-240.33630932474
DeepCCS[M+Na]+215.31830932474
AllCCS[M+H]+207.532859911
AllCCS[M+H-H2O]+205.332859911
AllCCS[M+NH4]+209.532859911
AllCCS[M+Na]+210.132859911
AllCCS[M-H]-208.032859911
AllCCS[M+Na-2H]-210.132859911
AllCCS[M+HCOO]-212.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
25-Hydroxyvitamin D2C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3647.8Standard polar33892256
25-Hydroxyvitamin D2C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3336.2Standard non polar33892256
25-Hydroxyvitamin D2C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C3430.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
25-Hydroxyvitamin D2,1TMS,isomer #1C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)CC[C@@H]123395.2Semi standard non polar33892256
25-Hydroxyvitamin D2,1TMS,isomer #2C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O)CC[C@@H]123354.0Semi standard non polar33892256
25-Hydroxyvitamin D2,2TMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C)CC[C@@H]123397.3Semi standard non polar33892256
25-Hydroxyvitamin D2,1TBDMS,isomer #1C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)CC[C@@H]123630.5Semi standard non polar33892256
25-Hydroxyvitamin D2,1TBDMS,isomer #2C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O)CC[C@@H]123578.5Semi standard non polar33892256
25-Hydroxyvitamin D2,2TBDMS,isomer #1C=C1CC[C@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@]2(C)C([C@H](C)/C=C/[C@H](C)C(C)(C)O[Si](C)(C)C(C)(C)C)CC[C@@H]123865.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-3019000000-36465aa35c47ab80eef32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D2 GC-MS (2 TMS) - 70eV, Positivesplash10-000x-1603390000-821c6f61bded227ff2712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D2 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 - 25-Hydroxyvitamin D2 10V, Positive-QTOFsplash10-01ot-0119200000-6a31a4086362269024cd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 20V, Positive-QTOFsplash10-0a6s-0459000000-45ba752a30c854da68cc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 40V, Positive-QTOFsplash10-0fj4-6395000000-2a0bb52b37082e56a80e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 10V, Negative-QTOFsplash10-03di-0005900000-3e4d6f3ace31e3d643212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 20V, Negative-QTOFsplash10-03dl-1009500000-7f5a0d3322017b58bde32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 40V, Negative-QTOFsplash10-000i-9208000000-069f4c813e56ffb206632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 10V, Negative-QTOFsplash10-03di-0002900000-39eecae8f9fc743e57082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 20V, Negative-QTOFsplash10-03dl-1109800000-22189a4f31317c5db4552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 40V, Negative-QTOFsplash10-056r-1119100000-5892af2e237af403d25d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 10V, Positive-QTOFsplash10-022a-0493100000-dbc8fa812c52d77c3d892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 20V, Positive-QTOFsplash10-0v4r-2193000000-6d9019ed5e8ff95fdb962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D2 40V, Positive-QTOFsplash10-014i-6971000000-63c804a7bc1e0f9a9f352021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0023 +/- 0.00033 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0097 (0.002-0.017) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0032 (0.0022-0.0042) uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0085 +/- 0.0295 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0879 +/- 0.023 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0347 +/- 0.0112 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.0059 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineDetected and Quantified0.008 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.0088 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.0088 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.01 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.01 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.000011 +/- 0.0000099 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0037 +/- 0.0016 uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome details
BloodDetected and Quantified0.046 (0.024-0.069) uMAdult (>18 years old)BothAnephrism details
BloodDetected and Quantified24233.741 uMChildren (1-13 years old)FemaleHyperphosphatasia details
UrineDetected and Quantified0.0003 (0.000017-0.00065) 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 ]
Smith-Lemli-Opitz syndrome
  1. Rossi M, Federico G, Corso G, Parenti G, Battagliese A, Frascogna AR, Della Casa R, Dello Russo A, Strisciuglio P, Saggese G, Andria G: Vitamin D status in patients affected by Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2005;28(1):69-80. [PubMed:15702407 ]
Hyperphosphatasia
  1. Saki F, Karamizadeh Z, Nasirabadi S, Mumm S, McAlister WH, Whyte MP: Juvenile paget's disease in an Iranian kindred with vitamin D deficiency and novel homozygous TNFRSF11B mutation. J Bone Miner Res. 2013 Jun;28(6):1501-8. doi: 10.1002/jbmr.1868. [PubMed:23322328 ]
Nephrotic syndrome
  1. Sato KA, Gray RW, Lemann J Jr: Urinary excretion of 25-hydroxyvitamin D in health and the nephrotic syndrome. J Lab Clin Med. 1982 Mar;99(3):325-30. [PubMed:6977006 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022621
KNApSAcK IDNot Available
Chemspider ID17216121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2289188
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833566
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH ID25HVITD2
MarkerDB IDMDB00000325
Good Scents IDNot Available
References
Synthesis ReferenceSardina, F. Javier; Mourino, Antonio; Castedo, Luis. Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2. Journal of Organic Chemistry (1986), 51(8), 1264-9.
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. 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 ]