Record Information
Version1.0
Creation date2010-04-08 22:14:26 UTC
Update date2017-03-11 22:59:26 UTC
Primary IDFDB019556
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namexi-8-Acetonyldihydrosanguinarine
Descriptionxi-8-Acetonyldihydrosanguinarine belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. xi-8-Acetonyldihydrosanguinarine is a moderately basic compound (based on its pKa).
CAS Number88588-10-7 37687-34-6
Structure
Thumb
Synonyms
SynonymSource
6-Acetonyl-5,6-dihydrosanguinarineKegg
(+/-)-8-acetonyldihydrosanguinarineKegg
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP3.44ALOGPS
logP3.82ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
pKa (Strongest Basic)1.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.17 m³·mol⁻¹ChemAxon
Polarizability41.22 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H19NO5
IUPAC name1-{24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaen-23-yl}propan-2-one
InChI IdentifierInChI=1S/C23H19NO5/c1-12(25)7-17-21-14(5-6-18-23(21)29-11-26-18)15-4-3-13-8-19-20(28-10-27-19)9-16(13)22(15)24(17)2/h3-6,8-9,17H,7,10-11H2,1-2H3
InChI KeyONEHMWWDDDSJBB-UHFFFAOYSA-N
Isomeric SMILESCN1C(CC(C)=O)C2=C(C=CC3=C2OCO3)C2=C1C1=CC3=C(OCO3)C=C1C=C2
Average Molecular Weight389.4007
Monoisotopic Molecular Weight389.126322723
Classification
Description Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBenzophenanthridine alkaloids
Sub ClassDihydrobenzophenanthridine alkaloids
Direct ParentDihydrobenzophenanthridine alkaloids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.94%; H 4.92%; N 3.60%; O 20.54%DFC
Melting PointMp 194-195.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSxi-8-Acetonyldihydrosanguinarine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2009000000-364461530c94110463f8Spectrum
Predicted GC-MSxi-8-Acetonyldihydrosanguinarine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0009000000-a9210693e08bd461c7b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-1009000000-95dab7d75068b2d63dceSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvl-4019000000-28c1e23170e0d65c1640Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-4f199831f3ef8da2d6bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-188316860990b073b6e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00tf-1009000000-a9270dd1276ced96622eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-3dc74d1aa25b63a7b857Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-2f1800b39acde55ecebbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap3-0009000000-47a254e9b6837d9e9781Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-d9b57af363c8fd7af69aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-0d2c364b894aafb08ec0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-0009000000-b73a932dc1997d01ff0fSpectrum
NMRNot Available
ChemSpider ID157916
ChEMBL IDNot Available
KEGG Compound IDC12201
Pubchem Compound ID181538
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39896
CRC / DFC (Dictionary of Food Compounds) IDHLG42-N:MCF92-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference