Showing Compound Charantin (FDB006198)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:02 UTC

Update date

2019-11-26 03:01:00 UTC

Primary ID

FDB006198

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Charantin

Description

Charantin, 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 Number

3200-06-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Naftidrofuryl oxalate	Kegg
Praxilene	Kegg
Naftidrofuryl oxalic acid	Generator
2-(Diethylamino)ethyl 3-(naphthalen-1-yl)-2-[(oxolan-2-yl)methyl]propanoate; oxalate	Generator
2-(Diethylamino)ethyl 3-(naphthalen-1-yl)-2-[(oxolan-2-yl)methyl]propanoic acid; oxalic acid	Generator
Nafronyl oxalic acid	Generator
Abbott brand OF naftidrofuryl oxalate	MeSH
Alpharma brand OF naftidrofuryl oxalate	MeSH
Artocoron	MeSH
Azunaftil	MeSH
Azupharma brand OF naftidrofuryl oxalate	MeSH
Di actane	MeSH
Di-actane	MeSH
DiActane	MeSH
Dusodril	MeSH
Faes brand OF naftidrofuryl oxalate	MeSH
Gévatran	MeSH
Hexal brand OF naftidrofuryl oxalate	MeSH
Lipha brand OF naftidrofuryl oxalate	MeSH
Menarini brand OF naftidrofuryl oxalate	MeSH
Merck brand OF nafronyl oxalate	MeSH
Merck lipha santé brand 1 OF naftidrofuryl oxalate	MeSH
Merck lipha santé brand 2 OF naftidrofuryl oxalate	MeSH
Nafronyl	MeSH
Nafronyloxalate	MeSH
Nafti puren	MeSH
Nafti ratiopharm	MeSH
Nafti-puren	MeSH
Nafti-ratiopharm	MeSH
NaftiPuren	MeSH
Naftidrofuryl	MeSH
Naftifurin oxalate	MeSH
Naftilong	MeSH
Naftilux	MeSH
Naftiratiopharm	MeSH
Oxalate, nafronyl	MeSH
Oxalate, naftifurin	MeSH
Thérabel brand OF naftidrofuryl oxalate	MeSH
CT Arzneimittel brand OF naftidrofuryl oxalate	MeSH
CT-Arzneimittel brand OF naftidrofuryl oxalate	MeSH
Nafti von CT	MeSH
Ratiopharm brand OF naftidrofuryl oxalate	MeSH
Nafronyl oxalate	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	0.00064 g/L	ALOGPS
logP	4.73	ALOGPS
logP	4.58	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	113.77 m³·mol⁻¹	ChemAxon
Polarizability	44.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C26H35NO7

IUPAC name

2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-[(oxolan-2-yl)methyl]propanoate; oxalic acid

InChI Identifier

InChI=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 Key

SSAJNPNVUYMUCI-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C(O)=O.CCN(CC)CCOC(=O)C(CC1CCCO1)CC1=CC=CC2=CC=CC=C12

Average Molecular Weight

473.566

Monoisotopic Molecular Weight

473.241352471

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

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 Framework

Not Available

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-dfcfd9f9748505622492	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000900000-dfcfd9f9748505622492	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000900000-dfcfd9f9748505622492	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-4d9be62db7af0fa309f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0000900000-4d9be62db7af0fa309f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0000900000-4d9be62db7af0fa309f1	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CHARANTIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti testicular			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE