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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:12 UTC
Update Date2022-03-07 02:52:12 UTC
HMDB IDHMDB0029567
Secondary Accession Numbers
  • HMDB29567
Metabolite Identification
Common NameHydroxy-alpha-sanshool
DescriptionHydroxy-alpha-sanshool belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, hydroxy-alpha-sanshool is considered to be a fatty amide. Based on a literature review a small amount of articles have been published on Hydroxy-alpha-sanshool.
Structure
Data?1582753436
Synonyms
ValueSource
Hydroxy-a-sanshoolGenerator
Hydroxy-α-sanshoolGenerator
Chemical FormulaC16H25NO2
Average Molecular Weight263.3752
Monoisotopic Molecular Weight263.188529049
IUPAC Name(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid
Traditional Name(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid
CAS Registry Number83883-10-7
SMILES
C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O
InChI Identifier
InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+
InChI KeyLHFKHAVGGJJQFF-JRNWQWJGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Tertiary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility33.25 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0072 g/LALOGPS
logP4.28ALOGPS
logP3.63ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity85.71 m³·mol⁻¹ChemAxon
Polarizability32.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+176.62430932474
DeepCCS[M-H]-174.26630932474
DeepCCS[M-2H]-207.15230932474
DeepCCS[M+Na]+182.71730932474
AllCCS[M+H]+168.432859911
AllCCS[M+H-H2O]+165.132859911
AllCCS[M+NH4]+171.532859911
AllCCS[M+Na]+172.432859911
AllCCS[M-H]-167.932859911
AllCCS[M+Na-2H]-168.932859911
AllCCS[M+HCOO]-170.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxy-alpha-sanshoolC\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O3403.3Standard polar33892256
Hydroxy-alpha-sanshoolC\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O2161.5Standard non polar33892256
Hydroxy-alpha-sanshoolC\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O2163.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxy-alpha-sanshool,1TMS,isomer #1C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O)O[Si](C)(C)C2277.8Semi standard non polar33892256
Hydroxy-alpha-sanshool,1TMS,isomer #2C/C=C\C=C\C=C/CC/C=C/C(O)=N/CC(C)(C)O[Si](C)(C)C2390.1Semi standard non polar33892256
Hydroxy-alpha-sanshool,2TMS,isomer #1C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C2373.7Semi standard non polar33892256
Hydroxy-alpha-sanshool,1TBDMS,isomer #1C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O)O[Si](C)(C)C(C)(C)C2488.8Semi standard non polar33892256
Hydroxy-alpha-sanshool,1TBDMS,isomer #2C/C=C\C=C\C=C/CC/C=C/C(O)=N/CC(C)(C)O[Si](C)(C)C(C)(C)C2590.0Semi standard non polar33892256
Hydroxy-alpha-sanshool,2TBDMS,isomer #1C/C=C\C=C\C=C/CC/C=C/C(=N/CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2781.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9640000000-d766379807b67f8a7da02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (2 TMS) - 70eV, Positivesplash10-001i-4944000000-655cbc0bdbbccd2125b02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy-alpha-sanshool GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy-alpha-sanshool 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 - Hydroxy-alpha-sanshool 10V, Positive-QTOFsplash10-01pa-9170000000-3edf9fccda30235c896e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Positive-QTOFsplash10-0079-9110000000-0eaf0328825abe309bb42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Positive-QTOFsplash10-00di-9100000000-76c392bd8a883d23e47d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Negative-QTOFsplash10-03di-0190000000-9dbd64116f2a467ceee52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Negative-QTOFsplash10-03dm-4980000000-1519aa203de14b7afb3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Negative-QTOFsplash10-007d-9700000000-d3dbe3db62be5cb1ef062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Negative-QTOFsplash10-03di-2090000000-2a87acc0fe5f25aec4692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Negative-QTOFsplash10-03dr-8980000000-aa93cc38ee943d1f0a862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Negative-QTOFsplash10-00kr-9800000000-e7d302c8b6dec6dd0a6f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 10V, Positive-QTOFsplash10-03di-2490000000-87d182707bad1650856f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 20V, Positive-QTOFsplash10-001l-9310000000-c70cb4872bbd1bd4df9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy-alpha-sanshool 40V, Positive-QTOFsplash10-004l-9100000000-68f630af9f9cbaa0c9aa2021-09-22Wishart 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 IDFDB000722
KNApSAcK IDC00056374
Chemspider ID30776781
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxy alpha sanshool
METLIN IDNot Available
PubChem Compound46870578
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810521
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.