Dihydrophaseic acid (CHEM032009)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:04:53 UTC
Update Date2016-11-09 01:19:23 UTC
Accession NumberCHEM032009
Identification
Common NameDihydrophaseic acid
ClassSmall Molecule
DescriptionIsolated from French beans. Dihydrophaseic acid is found in many foods, some of which are sunflower, corn, pulses, and coconut.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DihydrophaseateGenerator
(-)-Dihydrophaseic acidHMDB
5-(3,8-Dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]oct-8-yl)-3-methyl-2,4-pentadienoic acid, 9ciHMDB
Chemical FormulaC15H22O5
Average Molecular Mass282.332 g/mol
Monoisotopic Mass282.147 g/mol
CAS Registry Number41756-77-8
IUPAC Name(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid
Traditional Name(2Z,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid
SMILESC\C(\C=C\C1(O)C2(C)COC1(C)CC(O)C2)=C\C(O)=O
InChI IdentifierInChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-
InChI KeyXIVFQYWMMJWUCD-IGTFLHFFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentAbscisic acids and derivatives
Alternative Parents
Substituents
  • Abscisic acid
  • Medium-chain fatty acid
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Oxepane
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility1.13 g/LALOGPS
logP0.62ALOGPS
logP0.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.57ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75 m³·mol⁻¹ChemAxon
Polarizability29.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-6390000000-15205983f888cc8aae34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00o0-5302900000-06eb8ff722caa23827b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0090000000-39cb65eb76c4015dff61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-0190000000-daee06671fa05492ff10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4i-6790000000-f456e9d8a76408cfbc3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-e1034d3cd46d13509eacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-1190000000-4a1fd8d5a91c0ecc7487Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-2890000000-5341ed0e427da270bdeeSpectrum
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 IDHMDB0038660
FooDB IDFDB018059
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24808182
ChEBI ID23758
PubChem Compound ID131752416
Kegg Compound IDC15971
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. D. C. Walton, B. Dorn, J. Fey, The isolation of an abscisic-acid metabolite, 4'-dihydrophaseic acid, from non-imbibed Phaseolus vulgaris seed, Planta (Berl.) 112, 87-90 (1973) [Isolation]
7. The lipid handbook with CD-ROM