Record Information
Version1.0
Creation date2010-04-08 22:07:02 UTC
Update date2019-11-26 03:01:00 UTC
Primary IDFDB006198
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCharantin
DescriptionCharantin, also known as naftidrofuryl or nafronyl, is a member of the class of compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Charantin is practically insoluble (in water) and a very strong basic compound (based on its pKa). Charantin can be found in bitter gourd, which makes charantin a potential biomarker for the consumption of this food product. Charantin is actually a 1:1 mixture of two steroidal saponins, β-sitosteryl glucoside (C 35H 60O 6) and 5,25-stigmasteryl glucoside (C 35H 58O 6). It is a whitish crystalline substance, neutral and tasteless, melting at 266–268 °C. It is sparingly soluble in water or other highly polar solvents, as well as in apolar solvents like hexane, but is soluble in ether, ethanol and methanol, and can be efficiently extracted from the plant by pressurized ethanol or acetone at 100 °C .
CAS Number3200-06-4
Structure
Thumb
Synonyms
SynonymSource
Naftidrofuryl oxalateKegg
PraxileneKegg
Naftidrofuryl oxalic acidGenerator
Nafronyl oxalic acidGenerator
Abbott brand OF naftidrofuryl oxalateMeSH
Alpharma brand OF naftidrofuryl oxalateMeSH
ArtocoronMeSH
AzunaftilMeSH
Azupharma brand OF naftidrofuryl oxalateMeSH
Di actaneMeSH
Di-actaneMeSH
DiActaneMeSH
DusodrilMeSH
Faes brand OF naftidrofuryl oxalateMeSH
GévatranMeSH
Hexal brand OF naftidrofuryl oxalateMeSH
Lipha brand OF naftidrofuryl oxalateMeSH
Menarini brand OF naftidrofuryl oxalateMeSH
Merck brand OF nafronyl oxalateMeSH
Merck lipha santé brand 1 OF naftidrofuryl oxalateMeSH
Merck lipha santé brand 2 OF naftidrofuryl oxalateMeSH
NafronylMeSH
NafronyloxalateMeSH
Nafti purenMeSH
Nafti ratiopharmMeSH
Nafti-purenMeSH
Nafti-ratiopharmMeSH
NaftiPurenMeSH
NaftidrofurylMeSH
Naftifurin oxalateMeSH
NaftilongMeSH
NaftiluxMeSH
NaftiratiopharmMeSH
Oxalate, nafronylMeSH
Oxalate, naftifurinMeSH
Thérabel brand OF naftidrofuryl oxalateMeSH
CT Arzneimittel brand OF naftidrofuryl oxalateMeSH
CT-Arzneimittel brand OF naftidrofuryl oxalateMeSH
Nafti von CTMeSH
Ratiopharm brand OF naftidrofuryl oxalateMeSH
Nafronyl oxalateMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP4.73ALOGPS
logP4.58ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity113.77 m³·mol⁻¹ChemAxon
Polarizability44.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H35NO7
IUPAC name2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-[(oxolan-2-yl)methyl]propanoate; oxalic acid
InChI IdentifierInChI=1S/C24H33NO3.C2H2O4/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20;3-1(4)2(5)6/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;(H,3,4)(H,5,6)
InChI KeySSAJNPNVUYMUCI-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C(O)=O.CCN(CC)CCOC(=O)C(CC1CCCO1)CC1=CC=CC2=CC=CC=C12
Average Molecular Weight473.566
Monoisotopic Molecular Weight473.241352471
Classification
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-dfcfd9f9748505622492Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000900000-dfcfd9f9748505622492Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000900000-dfcfd9f9748505622492Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-4d9be62db7af0fa309f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-4d9be62db7af0fa309f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000900000-4d9be62db7af0fa309f1Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCHARANTIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti testicularDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).