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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:17 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030176
Secondary Accession Numbers
  • HMDB30176
Metabolite Identification
Common NameNorsanguinarine
DescriptionNorsanguinarine, also known as 2,3, belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. Based on a literature review a significant number of articles have been published on Norsanguinarine.
Structure
Data?1600212096
Synonyms
ValueSource
(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-I)phenanthridineHMDB
1,3-Dioxolo(I)(1,3)dioxolo(4,5)benzo(1,2-c)phenanthridineHMDB
1,3-Dioxolo[I][1,3]dioxolo[4,5]benzo[1,2-c]phenanthridineHMDB
13-Demethyl-sanguinarineHMDB
2,3HMDB
7,8-Bis(methylenedioxy)benzo[c]phenanthridineHMDB
DihydrosanguinarineHMDB
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-I]phenanthridineHMDB
13-DemethylsanguinarineHMDB
DemethylsanguinarineHMDB
N-NorsanguinarineHMDB
NorsanguinarineMeSH
Chemical FormulaC19H11NO4
Average Molecular Weight317.2949
Monoisotopic Molecular Weight317.068807845
IUPAC Name5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
Traditional Name5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
CAS Registry Number522-30-5
SMILES
C1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C2
InChI Identifier
InChI=1S/C19H11NO4/c1-2-12-11-3-4-15-19(24-9-21-15)14(11)7-20-18(12)13-6-17-16(5-10(1)13)22-8-23-17/h1-7H,8-9H2
InChI KeyCNXVDVMAYXLWPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentPhenanthridines and derivatives
Alternative Parents
Substituents
  • Phenanthridine
  • Isoquinoline
  • Naphthalene
  • Benzodioxole
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point285 - 287 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP3.61ALOGPS
logP3.36ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)4.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.81 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.41 m³·mol⁻¹ChemAxon
Polarizability33.17 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]+170.57731661259
DarkChem[M-H]-174.7631661259
DeepCCS[M-2H]-220.00430932474
DeepCCS[M+Na]+195.67730932474
AllCCS[M+H]+174.132859911
AllCCS[M+H-H2O]+170.532859911
AllCCS[M+NH4]+177.332859911
AllCCS[M+Na]+178.332859911
AllCCS[M-H]-178.132859911
AllCCS[M+Na-2H]-176.632859911
AllCCS[M+HCOO]-175.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorsanguinarineC1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C24405.6Standard polar33892256
NorsanguinarineC1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C22896.3Standard non polar33892256
NorsanguinarineC1OC2=C(O1)C=C1C(C=CC3=C4C=CC5=C(OCO5)C4=CN=C13)=C23407.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norsanguinarine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1289000000-030ebf995d568cd09ccd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norsanguinarine 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 - Norsanguinarine 10V, Positive-QTOFsplash10-014i-0009000000-d38f3b692115364c5b2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 20V, Positive-QTOFsplash10-014i-0009000000-b0a36b2176aa875f1d562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 40V, Positive-QTOFsplash10-00di-0092000000-70928fb95ffcf8e3f05b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 10V, Negative-QTOFsplash10-014i-0009000000-7997eb6006f3e07da70c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 20V, Negative-QTOFsplash10-014i-0009000000-fd34fc3396df9b21bbed2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 40V, Negative-QTOFsplash10-01b9-0079000000-5c74b62bff7c51937be92016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 10V, Negative-QTOFsplash10-014i-0009000000-cdb697e9f2878552c94c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 20V, Negative-QTOFsplash10-014i-0029000000-510145a97d282a2483bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 40V, Negative-QTOFsplash10-000i-0091000000-961350d21ad47df1f4392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 10V, Positive-QTOFsplash10-014i-0009000000-7a22534e87f602b14ab32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 20V, Positive-QTOFsplash10-014i-0019000000-a616b24aed205ed9252c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norsanguinarine 40V, Positive-QTOFsplash10-0006-0090000000-328d9a56a7c6e865c9de2021-09-25Wishart 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 IDFDB001992
KNApSAcK IDC00024657
Chemspider ID88162
KEGG Compound IDC05191
BioCyc IDDIHYDROSANGUINARINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97679
PDB IDNot Available
ChEBI ID17209
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.. .