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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:41 UTC
Update Date2019-01-11 19:39:53 UTC
HMDB IDHMDB0030246
Secondary Accession Numbers
  • HMDB30246
Metabolite Identification
Common NameNarceine
DescriptionNarceine is found in opium poppy. Narceine is an alkaloid from Papaver somniferum (opium poppy
Structure
Data?1547235593
Synonyms
ValueSource
6-[[6-[2-(dimethylamino)Ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid, 9ciHMDB
NarceinHMDB
Chemical FormulaC23H27NO8
Average Molecular Weight445.4624
Monoisotopic Molecular Weight445.173666845
IUPAC Name6-(2-{6-[2-(dimethylamino)ethyl]-4-methoxy-2H-1,3-benzodioxol-5-yl}acetyl)-2,3-dimethoxybenzoic acid
Traditional Namenarceine
CAS Registry Number131-28-2
SMILES
COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C
InChI Identifier
InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)
InChI KeyDEXMFYZAHXMZNM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Alkyl-phenylketone
  • M-methoxybenzoic acid or derivatives
  • O-methoxybenzoic acid or derivatives
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Benzodioxole
  • Benzoic acid or derivatives
  • Benzoic acid
  • Phenylketone
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Methoxybenzene
  • Aralkylamine
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Amino acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.78 mg/mL at 13 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.06ALOGPS
logP-0.33ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)8.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity116.89 m³·mol⁻¹ChemAxon
Polarizability45.95 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9210000000-c6c3c934ee19f8db8182JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9210000000-c6c3c934ee19f8db8182JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9541400000-7d48e466a1cce6c33aacJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9130320000-183831bca24f6c6d5f01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fba-0001900000-10183188673951773c03JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug0-0234900000-389e5ae29d869375d246JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-0988000000-9637b882287fce432f36JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0001900000-ddb55e74e09433b0f01dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fai-0119700000-0afc1dc554a44d8ee2c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-1209000000-5a110b49ba3963712d0fJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB002069
KNApSAcK IDC00001890
Chemspider ID8246
KEGG Compound IDC09591
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNarceine
METLIN IDNot Available
PubChem Compound8564
PDB IDNot Available
ChEBI ID623301
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.. .