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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:26:14 UTC
Update Date2022-03-07 02:56:23 UTC
HMDB IDHMDB0039896
Secondary Accession Numbers
  • HMDB39896
Metabolite Identification
Common 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 an alkaloid from Papaver somniferum (opium poppy). xi-8-Acetonyldihydrosanguinarine is a moderately basic compound (based on its pKa).
Structure
Data?1563863456
Synonyms
ValueSource
6-Acetonyl-5,6-dihydrosanguinarineKegg
(+/-)-8-acetonyldihydrosanguinarineKegg
Chemical FormulaC23H19NO5
Average Molecular Weight389.4007
Monoisotopic Molecular Weight389.126322723
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
Traditional 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
CAS Registry NumberNot Available
SMILES
CN1C(CC(C)=O)C2=C(C=CC3=C2OCO3)C2=C1C1=CC3=C(OCO3)C=C1C=C2
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 195.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.25831661259
DarkChem[M-H]-186.12831661259
DeepCCS[M+H]+187.73330932474
DeepCCS[M-H]-185.37530932474
DeepCCS[M-2H]-219.7230932474
DeepCCS[M+Na]+194.81730932474
AllCCS[M+H]+193.332859911
AllCCS[M+H-H2O]+190.432859911
AllCCS[M+NH4]+196.032859911
AllCCS[M+Na]+196.832859911
AllCCS[M-H]-198.732859911
AllCCS[M+Na-2H]-198.232859911
AllCCS[M+HCOO]-197.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-8-AcetonyldihydrosanguinarineCN1C(CC(C)=O)C2=C(C=CC3=C2OCO3)C2=C1C1=CC3=C(OCO3)C=C1C=C24935.1Standard polar33892256
xi-8-AcetonyldihydrosanguinarineCN1C(CC(C)=O)C2=C(C=CC3=C2OCO3)C2=C1C1=CC3=C(OCO3)C=C1C=C23187.5Standard non polar33892256
xi-8-AcetonyldihydrosanguinarineCN1C(CC(C)=O)C2=C(C=CC3=C2OCO3)C2=C1C1=CC3=C(OCO3)C=C1C=C23550.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
xi-8-Acetonyldihydrosanguinarine,1TMS,isomer #1CC(=CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C3682.2Semi standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TMS,isomer #1CC(=CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C3313.3Standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TMS,isomer #2C=C(CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C3604.3Semi standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TMS,isomer #2C=C(CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C3328.3Standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TBDMS,isomer #1CC(=CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C(C)(C)C3912.4Semi standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TBDMS,isomer #1CC(=CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C(C)(C)C3552.8Standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TBDMS,isomer #2C=C(CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C(C)(C)C3856.2Semi standard non polar33892256
xi-8-Acetonyldihydrosanguinarine,1TBDMS,isomer #2C=C(CC1C2=C(C=CC3=C2OCO3)C2=CC=C3C=C4OCOC4=CC3=C2N1C)O[Si](C)(C)C(C)(C)C3548.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Acetonyldihydrosanguinarine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2009000000-364461530c94110463f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Acetonyldihydrosanguinarine 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 - xi-8-Acetonyldihydrosanguinarine 10V, Positive-QTOFsplash10-006x-0009000000-a9210693e08bd461c7b52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 20V, Positive-QTOFsplash10-00dl-1009000000-95dab7d75068b2d63dce2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 40V, Positive-QTOFsplash10-0fvl-4019000000-28c1e23170e0d65c16402016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 10V, Negative-QTOFsplash10-000i-0009000000-4f199831f3ef8da2d6bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 20V, Negative-QTOFsplash10-000i-0009000000-188316860990b073b6e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 40V, Negative-QTOFsplash10-00tf-1009000000-a9270dd1276ced96622e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 10V, Negative-QTOFsplash10-000i-0009000000-3dc74d1aa25b63a7b8572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 20V, Negative-QTOFsplash10-000i-0009000000-2f1800b39acde55ecebb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 40V, Negative-QTOFsplash10-0ap3-0009000000-47a254e9b6837d9e97812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 10V, Positive-QTOFsplash10-0006-0009000000-d9b57af363c8fd7af69a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 20V, Positive-QTOFsplash10-0002-0009000000-0d2c364b894aafb08ec02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Acetonyldihydrosanguinarine 40V, Positive-QTOFsplash10-0gbc-0009000000-b73a932dc1997d01ff0f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB019556
KNApSAcK IDC00024626 C00027777
Chemspider ID157916
KEGG Compound IDC12201
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound181538
PDB IDNot Available
ChEBI ID31022
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .