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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:56:37 UTC
Update Date2022-03-07 03:17:39 UTC
HMDB IDHMDB0060127
Secondary Accession Numbers
  • HMDB60127
Metabolite Identification
Common Name25-Hydroxyvitamin D3-26,23-lactol
Description25-Hydroxyvitamin D3-26,23-lactol 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. 25-Hydroxyvitamin D3-26,23-lactol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866018
SynonymsNot Available
Chemical FormulaC27H42O4
Average Molecular Weight430.62
Monoisotopic Molecular Weight430.308309832
IUPAC Name(2R,3R,5R)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-{2-[(1E,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]propyl]-3-methyloxolane-2,3-diol
Traditional Name(2R,3R,5R)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-{2-[(1E,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]propyl]-3-methyloxolane-2,3-diol
CAS Registry NumberNot Available
SMILES
C[C@H](C[C@@H]1C[C@@](C)(O)[C@H](O)O1)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1/C[C@H](O)CCC1=C
InChI Identifier
InChI=1S/C27H42O4/c1-17-7-10-21(28)15-20(17)9-8-19-6-5-13-26(3)23(11-12-24(19)26)18(2)14-22-16-27(4,30)25(29)31-22/h8-9,18,21-25,28-30H,1,5-7,10-16H2,2-4H3/b19-8+,20-9+/t18-,21-,22-,23-,24+,25-,26-,27-/m1/s1
InChI KeySFOPTSUKUQDFIB-LSTZBGQISA-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
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.012 g/LALOGPS
logP4.54ALOGPS
logP3.95ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)11.26ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.75 m³·mol⁻¹ChemAxon
Polarizability51.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.4931661259
DarkChem[M-H]-200.96131661259
DeepCCS[M-2H]-235.80830932474
DeepCCS[M+Na]+210.01330932474
AllCCS[M+H]+210.932859911
AllCCS[M+H-H2O]+208.832859911
AllCCS[M+NH4]+212.932859911
AllCCS[M+Na]+213.532859911
AllCCS[M-H]-209.132859911
AllCCS[M+Na-2H]-211.032859911
AllCCS[M+HCOO]-213.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
25-Hydroxyvitamin D3-26,23-lactolC[C@H](C[C@@H]1C[C@@](C)(O)[C@H](O)O1)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1/C[C@H](O)CCC1=C3789.3Standard polar33892256
25-Hydroxyvitamin D3-26,23-lactolC[C@H](C[C@@H]1C[C@@](C)(O)[C@H](O)O1)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1/C[C@H](O)CCC1=C3436.7Standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactolC[C@H](C[C@@H]1C[C@@](C)(O)[C@H](O)O1)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1/C[C@H](O)CCC1=C3689.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
25-Hydroxyvitamin D3-26,23-lactol,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)C[C@@H]1C[C@@](C)(O[Si](C)(C)C)[C@H](O)O13509.3Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,1TMS,isomer #2C=C1CC[C@@H](O)C/C1=C\C=C1/CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)C[C@@H]1C[C@@](C)(O)[C@H](O[Si](C)(C)C)O13471.6Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,1TMS,isomer #3C=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@@H]1C[C@@](C)(O)[C@H](O)O13395.4Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,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)C[C@@H]1C[C@@](C)(O[Si](C)(C)C)[C@H](O)O13465.3Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,2TMS,isomer #2C=C1CC[C@@H](O)C/C1=C\C=C1/CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)C[C@@H]1C[C@@](C)(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)O13532.9Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,2TMS,isomer #3C=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@@H]1C[C@@](C)(O)[C@H](O[Si](C)(C)C)O13441.3Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,3TMS,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@@H]1C[C@@](C)(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)O13508.3Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,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)C[C@@H]1C[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H](O)O13761.4Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,1TBDMS,isomer #2C=C1CC[C@@H](O)C/C1=C\C=C1/CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)C[C@@H]1C[C@@](C)(O)[C@H](O[Si](C)(C)C(C)(C)C)O13723.3Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,1TBDMS,isomer #3C=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@@H]1C[C@@](C)(O)[C@H](O)O13627.0Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,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)C[C@@H]1C[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H](O)O13942.6Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,2TBDMS,isomer #2C=C1CC[C@@H](O)C/C1=C\C=C1/CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@H](C)C[C@@H]1C[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)O14016.0Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,2TBDMS,isomer #3C=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@@H]1C[C@@](C)(O)[C@H](O[Si](C)(C)C(C)(C)C)O13893.4Semi standard non polar33892256
25-Hydroxyvitamin D3-26,23-lactol,3TBDMS,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@@H]1C[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)O14175.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1113039000-be1fbcacc9f03b8cee5e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 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 D3-26,23-lactol 10V, Positive-QTOFsplash10-03e9-0117900000-c9cded915b4c2e58b31b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 20V, Positive-QTOFsplash10-0bu0-0519300000-4a430d22777afdea7d482019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 40V, Positive-QTOFsplash10-0fgc-4897200000-6c8e4d2be0423c10ec232019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 10V, Negative-QTOFsplash10-004i-0001900000-c1bb28c4a6c480e907d12019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 20V, Negative-QTOFsplash10-03g0-4001900000-ab981e23e65c35189c0a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 25-Hydroxyvitamin D3-26,23-lactol 40V, Negative-QTOFsplash10-052r-2019000000-19ec041a188fe7b765f72019-02-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769837
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.