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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:53:55 UTC
Update Date2019-07-23 06:15:11 UTC
HMDB IDHMDB0034104
Secondary Accession Numbers
  • HMDB34104
Metabolite Identification
Common NameNeferine
DescriptionNeferine is found in coffee and coffee products. Neferine is an alkaloid from the seed embryo of Nelumbo nucifera (East Indian lotus
Structure
Data?1563862511
Synonyms
ValueSource
12'-O-MethylliensinineHMDB
NeferinHMDB
Chemical FormulaC38H44N2O6
Average Molecular Weight624.7658
Monoisotopic Molecular Weight624.31993715
IUPAC Name4-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)phenol
Traditional Name4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl)methyl]-2-({6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl}oxy)phenol
CAS Registry Number2292-16-2
SMILES
COC1=CC=C(CC2N(C)CCC3=CC(OC)=C(OC4=C(O)C=CC(CC5N(C)CCC6=CC(OC)=C(OC)C=C56)=C4)C=C23)C=C1
InChI Identifier
InChI=1S/C38H44N2O6/c1-39-15-14-27-21-36(44-5)38(23-30(27)31(39)17-24-7-10-28(42-3)11-8-24)46-34-19-25(9-12-33(34)41)18-32-29-22-37(45-6)35(43-4)20-26(29)13-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3
InChI KeyMIBATSHDJRIUJK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP5.94ALOGPS
logP5.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)8.98ChemAxon
pKa (Strongest Basic)8.42ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.86 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity181.91 m³·mol⁻¹ChemAxon
Polarizability70.17 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0090110000-5011ddd749bf2582c46fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-0090011000-35c242e0fe8b2bfe8bdcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000049000-d2b32b64d549c2e8f761JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4m-0351392000-3658f0c63fd419dd7f0eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0981122000-bc32da800294e1a60b88JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001009000-df184214f3d21176140bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-076r-0047039000-05f9f4d9fecfa02fa1e3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0094000000-27a6f5eec68243c466e2JSpectraViewer | MoNA
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
FoodDB IDFDB012368
KNApSAcK IDNot Available
Chemspider ID353522
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound398793
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sugimoto Y, Furutani S, Itoh A, Tanahashi T, Nakajima H, Oshiro H, Sun S, Yamada J: Effects of extracts and neferine from the embryo of Nelumbo nucifera seeds on the central nervous system. Phytomedicine. 2008 Dec;15(12):1117-24. doi: 10.1016/j.phymed.2008.09.005. [PubMed:19010651 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .