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Record Information
Version1.0
Creation Date2016-05-25 21:24:39 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023986
Identification
Common Name(+)-2,3-Dihydro-9-hydroxy-2[1-(6-sinapinoyl)beta-D-glucosyloxy-1-methylethyl]-7H-furo[3,2-g][1]benzopyran-7-one
ClassSmall Molecule
Description(+)-2,3-dihydro-9-hydroxy-2[1-(6-sinapinoyl)beta-d-glucosyloxy-1-methylethyl]-7h-furo[3,2-g][1]benzopyran-7-one is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (+)-2,3-dihydro-9-hydroxy-2[1-(6-sinapinoyl)beta-d-glucosyloxy-1-methylethyl]-7h-furo[3,2-g][1]benzopyran-7-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-2,3-dihydro-9-hydroxy-2[1-(6-sinapinoyl)beta-d-glucosyloxy-1-methylethyl]-7h-furo[3,2-g][1]benzopyran-7-one can be found in wild celery, which makes (+)-2,3-dihydro-9-hydroxy-2[1-(6-sinapinoyl)beta-d-glucosyloxy-1-methylethyl]-7h-furo[3,2-g][1]benzopyran-7-one a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(+)-2,3-Dihydro-9-hydroxy-2[1-(6-sinapinoyl)b-D-glucosyloxy-1-methylethyl]-7H-furo[3,2-g][1]benzopyran-7-oneGenerator
(+)-2,3-Dihydro-9-hydroxy-2[1-(6-sinapinoyl)β-D-glucosyloxy-1-methylethyl]-7H-furo[3,2-g][1]benzopyran-7-oneGenerator
Chemical FormulaC31H34O14
Average Molecular Mass630.593 g/mol
Monoisotopic Mass630.195 g/mol
CAS Registry Number115235-61-5
IUPAC Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2R)-9-hydroxy-7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[(2R)-9-hydroxy-7-oxo-2H,3H-furo[3,2-g]chromen-2-yl]propan-2-yl}oxy)oxan-2-yl]methyl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
SMILESCOC1=CC(\C=C\C(=O)OC[C@H]2O[C@@H](OC(C)(C)[C@H]3CC4=CC5=C(OC(=O)C=C5)C(O)=C4O3)[C@H](O)[C@@H](O)[C@@H]2O)=CC(OC)=C1O
InChI IdentifierInChI=1S/C31H34O14/c1-31(2,20-12-16-11-15-6-8-22(33)44-28(15)27(38)29(16)43-20)45-30-26(37)25(36)24(35)19(42-30)13-41-21(32)7-5-14-9-17(39-3)23(34)18(10-14)40-4/h5-11,19-20,24-26,30,34-38H,12-13H2,1-4H3/b7-5+/t19-,20-,24-,25+,26-,30+/m1/s1
InChI KeyIVHSSCUMYDHEGB-XRTQGIEQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassNot Available
Direct ParentCytochalasans
Alternative Parents
Substituents
  • Carbocyclic cytochalasan skeleton
  • Cytochalasan
  • Isoindolone
  • Isoindoline
  • Isoindole
  • Isoindole or derivatives
  • Monocyclic benzene moiety
  • Pyrrolidone
  • 2-pyrrolidone
  • Benzenoid
  • Tertiary alcohol
  • Pyrrolidine
  • Cyclic alcohol
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.13 g/LALOGPS
logP2.3ALOGPS
logP2.72ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area199.9 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity155.21 m³·mol⁻¹ChemAxon
Polarizability62.43 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-0390102000-0f2eb38d2689f9334096View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0190000000-551b5a1a5fc21135c796View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002v-0910000000-db0f46ac728ca3556c20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0c29-0092002000-65f33d0076cd07ec8745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-096r-0190000000-d6213d42a032e5dffabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ck9-0290000000-10e2ec205ed83d1448bcView in MoNA
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 IDNot Available
FooDB IDFDB001752
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 IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available