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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:10:28 UTC
Update Date2022-03-07 02:53:42 UTC
HMDB IDHMDB0033440
Secondary Accession Numbers
  • HMDB33440
Metabolite Identification
Common NameNarcotoline
DescriptionNarcotoline is found in opium poppy. Narcotoline is an alkaloid from straw of Papaver somniferum (opium poppy) Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media. It can be obtained from the opium poppy Papaver somniferum. It is present at much higher levels in strains used for culinary purposes (poppyseed production) than in high-morphine strains used for opium production.
Structure
Data?1563862406
SynonymsNot Available
Chemical FormulaC21H21NO7
Average Molecular Weight399.3939
Monoisotopic Molecular Weight399.131802031
IUPAC Name3-{4-hydroxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one
Traditional Name3-{4-hydroxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-6,7-dimethoxy-3H-2-benzofuran-1-one
CAS Registry Number521-40-4
SMILES
COC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C12
InChI Identifier
InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3
InChI KeyLMGZCSKYOKDBES-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassPhthalide isoquinolines
Sub ClassNot Available
Direct ParentPhthalide isoquinolines
Alternative Parents
Substituents
  • Phthalide isoquinoline
  • Phthalide
  • Isobenzofuranone
  • Benzofuranone
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Isocoumaran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxylic acid ester
  • Tertiary amine
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP1.98ALOGPS
logP1.42ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.1ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability40.42 ųChemAxon
Number of Rings5ChemAxon
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]+189.53431661259
DarkChem[M-H]-186.62731661259
DeepCCS[M-2H]-220.36130932474
DeepCCS[M+Na]+195.58930932474
AllCCS[M+H]+194.132859911
AllCCS[M+H-H2O]+191.432859911
AllCCS[M+NH4]+196.732859911
AllCCS[M+Na]+197.432859911
AllCCS[M-H]-197.932859911
AllCCS[M+Na-2H]-197.732859911
AllCCS[M+HCOO]-197.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NarcotolineCOC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C124546.4Standard polar33892256
NarcotolineCOC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C123164.4Standard non polar33892256
NarcotolineCOC1=C(OC)C2=C(C=C1)C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(O)=C123228.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Narcotoline,1TMS,isomer #1COC1=CC=C2C(=C1OC)C(=O)OC2C1C2=C(O[Si](C)(C)C)C3=C(C=C2CCN1C)OCO33224.3Semi standard non polar33892256
Narcotoline,1TBDMS,isomer #1COC1=CC=C2C(=C1OC)C(=O)OC2C1C2=C(O[Si](C)(C)C(C)(C)C)C3=C(C=C2CCN1C)OCO33444.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Narcotoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0090000000-8d36861fe0a3f59dbd492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narcotoline GC-MS (1 TMS) - 70eV, Positivesplash10-004i-0090000000-83da6a230540709d25ed2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narcotoline 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 - Narcotoline 10V, Positive-QTOFsplash10-0udi-0012900000-eb91c9a66be98f3a0e6a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 20V, Positive-QTOFsplash10-0zfr-0439500000-73d8dce5952ad6dabd422015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 40V, Positive-QTOFsplash10-004i-1913000000-f9a62eb623879958a12a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 10V, Negative-QTOFsplash10-0002-0009000000-46306f2e15cf4d8ab3862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 20V, Negative-QTOFsplash10-000t-0009000000-4f29fdfaf4b68c9a43802015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 40V, Negative-QTOFsplash10-0f7a-4149000000-ae5a71e7bcc549404f182015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 10V, Negative-QTOFsplash10-0002-0009000000-493e5720e60337ba3deb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 20V, Negative-QTOFsplash10-0002-0009000000-78f035578ab74eed99fa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 40V, Negative-QTOFsplash10-0lxw-0529000000-1cb32954177b072022c82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 10V, Positive-QTOFsplash10-0udi-0010900000-00307be5f0edf24e3e7d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 20V, Positive-QTOFsplash10-0udi-0021900000-5a924610ef954314a3862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narcotoline 40V, Positive-QTOFsplash10-0690-0977000000-146ce1b694343cd559a72021-09-25Wishart LabView Spectrum
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
FooDB IDFDB011478
KNApSAcK IDC00001892
Chemspider ID2736756
KEGG Compound IDC09593
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNarcotoline
METLIN IDNot Available
PubChem Compound3496496
PDB IDNot Available
ChEBI IDNot Available
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.. .