Azaspiracid 2 (CHEM031612)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:46:50 UTC
Update Date2016-11-09 01:19:18 UTC
Accession NumberCHEM031612
Identification
Common NameAzaspiracid 2
ClassSmall Molecule
DescriptionStress metabolite of Ipomoea batatas (sweet potato). (2E,6E)-1-Hydroxy-2,6,10-farnesatrien-9-one is found in root vegetables and potato.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-4'',6-dimethyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoateGenerator
Azaspiracid-2MeSH
Chemical FormulaC48H73NO12
Average Molecular Mass856.093 g/mol
Monoisotopic Mass855.513 g/mol
CAS Registry Number265996-92-7
IUPAC Name(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-4'',6-dimethyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid
Traditional Name(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-4'',6-dimethyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid
SMILESCC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC(C)=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1
InChI IdentifierInChI=1S/C48H73NO12/c1-26-16-34(11-9-10-12-40(50)51)55-44(21-26)13-14-47(61-44)32(7)19-35-36(58-47)20-38(54-35)43(52)48(53)33(8)18-29(4)41(60-48)30(5)23-45-22-27(2)17-37(56-45)42-39(57-45)24-46(59-42)31(6)15-28(3)25-49-46/h9,11,16,27-29,31-39,41-43,49,52-53H,5,10,12-15,17-25H2,1-4,6-8H3,(H,50,51)/b11-9+
InChI KeyFWMJPUBOGPIFOU-PKNBQFBNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0023 g/LALOGPS
logP3.72ALOGPS
logP4.97ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area163.63 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity226.2 m³·mol⁻¹ChemAxon
Polarizability96.25 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0khi-0509410040-6e370224026ff6849dfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-1709021100-b0a5ee6b26286eda7bb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0100-3901000000-f32a2113b551b6abe4e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gxt-2831981040-022e1459577d65f54fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bl-0384631290-f873a04c4411035b047bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1910000000-99ec8345fb81011a8a67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001001090-c2a279d718daef2d841fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0007610090-ca90305caa2f4380d49aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-0901200530-5a909cbbd855cce65bc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000010090-f3eb54f44f8c6c76244cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3032200090-4d641c0ec89b6066d495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ir-2490002010-069e761ee6463e09d476Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030891
FooDB IDFDB002855
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID101648402
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM