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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:46 UTC
Update Date2022-03-07 02:53:17 UTC
HMDB IDHMDB0032256
Secondary Accession Numbers
  • HMDB32256
Metabolite Identification
Common Name(+-)-Ethyl 3-hydroxy-2-methylbutyrate
Description(+-)-Ethyl 3-hydroxy-2-methylbutyrate 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 a small amount of articles have been published on (+-)-Ethyl 3-hydroxy-2-methylbutyrate.
Structure
Data?1563862239
Synonyms
ValueSource
(+-)-Ethyl 3-hydroxy-2-methylbutyric acidGenerator
(+/-)-ethyl 3-hydroxy-2-methylbutyric acidHMDB
Chemical FormulaC30H48O3
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,5E)-7-ethyl-7-hydroxynon-5-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,5E)-7-ethyl-7-hydroxynon-5-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
CAS Registry Number27372-03-8
SMILES
CCC(O)(CC)\C=C\CC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C
InChI Identifier
InChI=1S/C30H48O3/c1-6-30(33,7-2)18-9-8-11-21(3)26-15-16-27-23(12-10-17-29(26,27)5)13-14-24-19-25(31)20-28(32)22(24)4/h9,13-14,18,21,25-28,31-33H,4,6-8,10-12,15-17,19-20H2,1-3,5H3/b18-9+,23-13+,24-14-/t21-,25-,26-,27+,28+,29-/m1/s1
InChI KeyDRYSPLCGYOPFPU-CQTNNHDRSA-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 effect
Disposition
Process
Role
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 Solubility0.0036 g/LALOGPS
logP6.81ALOGPS
logP5.63ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity141.14 m³·mol⁻¹ChemAxon
Polarizability56.74 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]+211.42131661259
DarkChem[M-H]-209.99131661259
DeepCCS[M-2H]-246.76930932474
DeepCCS[M+Na]+221.00430932474
AllCCS[M+H]+218.032859911
AllCCS[M+H-H2O]+216.132859911
AllCCS[M+NH4]+219.732859911
AllCCS[M+Na]+220.232859911
AllCCS[M-H]-213.332859911
AllCCS[M+Na-2H]-216.132859911
AllCCS[M+HCOO]-219.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+-)-Ethyl 3-hydroxy-2-methylbutyrateCCC(O)(CC)\C=C\CC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C3874.0Standard polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrateCCC(O)(CC)\C=C\CC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C3561.8Standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrateCCC(O)(CC)\C=C\CC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C3845.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O3754.4Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O[Si](C)(C)C)C[C@@H]1O3650.2Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O)C[C@@H]1O[Si](C)(C)C3643.2Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O3637.2Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C3613.8Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3533.4Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,3TMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3556.8Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O3983.9Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TBDMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O3847.4Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,1TBDMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C3827.5Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O4105.0Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TBDMS,isomer #2C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C(C)(C)C)C[C@@H](O)C[C@@H]1O[Si](C)(C)C(C)(C)C4062.2Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,2TBDMS,isomer #3C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(O)(CC)CC)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3937.0Semi standard non polar33892256
(+-)-Ethyl 3-hydroxy-2-methylbutyrate,3TBDMS,isomer #1C=C1/C(=C\C=C2/CCC[C@@]3(C)[C@H]2CC[C@@H]3[C@H](C)CC/C=C/C(CC)(CC)O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C4210.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01s9-1114900000-a3b643cdfcdad9a59e842017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate GC-MS (3 TMS) - 70eV, Positivesplash10-0a4l-1000129000-9bc6e7d7da769907f3fe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 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 - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 10V, Positive-QTOFsplash10-0079-0001900000-3324eb4d2f00f3aba85d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 20V, Positive-QTOFsplash10-00dr-1637900000-68c385cb15d88aa05fa72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 40V, Positive-QTOFsplash10-00kr-4549100000-e39fc9feee4a14b5f6c02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 10V, Negative-QTOFsplash10-0a4i-0000900000-9178262f3b60de9e50032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 20V, Negative-QTOFsplash10-052r-0001900000-8824dd90bb72b00bb8832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 40V, Negative-QTOFsplash10-0079-7205900000-54db048db945205ca1252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 10V, Positive-QTOFsplash10-059i-0147900000-4f73918883665010ea4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 20V, Positive-QTOFsplash10-014r-4094100000-c52a508a8f4d34d1fe0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 40V, Positive-QTOFsplash10-029i-3891100000-5f5484cf6b30d4defd4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 10V, Negative-QTOFsplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 20V, Negative-QTOFsplash10-0a4i-0202900000-f10b0207ec90e49342612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+-)-Ethyl 3-hydroxy-2-methylbutyrate 40V, Negative-QTOFsplash10-0a4i-0304900000-9236f4c6c63a5979bfa12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB009368
KNApSAcK IDNot Available
Chemspider ID10160255
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11987778
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.