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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:52:58 UTC
Update Date2022-03-07 02:55:49 UTC
HMDB IDHMDB0038559
Secondary Accession Numbers
  • HMDB38559
Metabolite Identification
Common Name8-Hexanoylneosolaniol
Description8-Hexanoylneosolaniol belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. 8-Hexanoylneosolaniol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863218
Synonyms
ValueSource
8-N-HexanoylneosolaniolHMDB
(1's,2S,2'r,4's,7'r,9'r,10'r,11's)-11'-(Acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl hexanoic acidGenerator
8-HexanoylneosolaniolMeSH
Chemical FormulaC25H36O9
Average Molecular Weight480.5479
Monoisotopic Molecular Weight480.23593275
IUPAC Name(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl hexanoate
Traditional Name(1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-11'-(acetyloxy)-2'-[(acetyloxy)methyl]-10'-hydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-4'-yl hexanoate
CAS Registry Number118143-01-4
SMILES
[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCCCC
InChI Identifier
InChI=1S/C25H36O9/c1-6-7-8-9-19(28)33-17-11-24(12-30-15(3)26)18(10-14(17)2)34-22-20(29)21(32-16(4)27)23(24,5)25(22)13-31-25/h10,17-18,20-22,29H,6-9,11-13H2,1-5H3/t17-,18+,20+,21+,22+,23+,24+,25-/m0/s1
InChI KeyNTQOBLPQKXJXCZ-RKESYOIOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentTrichothecenes
Alternative Parents
Substituents
  • Trichothecene skeleton
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Oxepane
  • Oxane
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.46ALOGPS
logP1.62ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area120.89 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity118.2 m³·mol⁻¹ChemAxon
Polarizability50.57 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+213.71131661259
DarkChem[M-H]-210.68931661259
DeepCCS[M-2H]-237.87830932474
DeepCCS[M+Na]+212.19230932474
AllCCS[M+H]+212.232859911
AllCCS[M+H-H2O]+210.632859911
AllCCS[M+NH4]+213.632859911
AllCCS[M+Na]+214.032859911
AllCCS[M-H]-209.132859911
AllCCS[M+Na-2H]-210.532859911
AllCCS[M+HCOO]-212.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Hexanoylneosolaniol[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCCCC3667.2Standard polar33892256
8-Hexanoylneosolaniol[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCCCC2883.5Standard non polar33892256
8-Hexanoylneosolaniol[H][C@@]12O[C@]3([H])C=C(C)[C@H](C[C@]3(COC(C)=O)[C@@](C)([C@H](OC(C)=O)[C@H]1O)[C@]21CO1)OC(=O)CCCCC2967.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hexanoylneosolaniol,1TMS,isomer #1CCCCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO22917.0Semi standard non polar33892256
8-Hexanoylneosolaniol,1TBDMS,isomer #1CCCCCC(=O)O[C@H]1C[C@@]2(COC(C)=O)[C@@H](C=C1C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](OC(C)=O)[C@@]2(C)[C@]12CO23155.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hexanoylneosolaniol GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-9168800000-88664bed9f193cfd2c7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hexanoylneosolaniol GC-MS (1 TMS) - 70eV, Positivesplash10-01vy-9045420000-7d1fe5b681abb4a22b692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hexanoylneosolaniol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hexanoylneosolaniol 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 - 8-Hexanoylneosolaniol 10V, Positive-QTOFsplash10-008a-3103900000-7bf0fe38f28bd23676902016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 20V, Positive-QTOFsplash10-00dj-8319400000-fb3cd5a8ffc8d8d8fb5e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 40V, Positive-QTOFsplash10-05fr-9106000000-e653e9fca982ffa364082016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 10V, Negative-QTOFsplash10-004r-3003900000-9c81bb4053d6f52d916c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 20V, Negative-QTOFsplash10-0aor-9306600000-3869a7575bb60e067b612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 40V, Negative-QTOFsplash10-0a4j-5900000000-bba09ae69d896dbafb882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 10V, Positive-QTOFsplash10-05gi-0009700000-c9452cda475fece9c7f42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 20V, Positive-QTOFsplash10-0a4i-2009100000-6f5d04e4b68e93ef624a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 40V, Positive-QTOFsplash10-053u-9002000000-b119582cfa63deb329d22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 10V, Negative-QTOFsplash10-0002-9002100000-156beea8838311ac51832021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 20V, Negative-QTOFsplash10-0a4i-9002000000-121dcc990e93339477ef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hexanoylneosolaniol 40V, Negative-QTOFsplash10-0006-9000000000-1babbb55a0fecacbb9932021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB017946
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14446336
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. (). 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.