Showing Compound Carpaine (FDB002103)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2020-02-24 19:10:24 UTC

Primary ID

FDB002103

Secondary Accession Numbers

FDB002105

Chemical Information

FooDB Name

Carpaine

Description

Alkaloid from leaves of Carica papaya (papaya) Carpaine is one of the major alkaloid components of papaya leaves which has been studied for its cardiovascular effects. Circulatory effects of carpaine were studied in Wistar male rats weighing 314 +/- 13 g, under pentobarbital (30 mg/kg) anesthesia. Increasing dosages of carpaine from 0.5 mg/kg to 2.0 mg/kg resulted in progressive decrease in systolic, diastolic, and mean arterial blood pressure. Selective autonomic nervous blockade with atropine sulfate (1 mg/kg) or propranolol hydrochloride (8 mg/kg) did not alter the circulatory response to carpaine. Carpaine, 2 mg/kg, reduced cardiac output, stroke volume, stroke work, and cardiac power, but the calculated total peripheral resistance remained unchanged. It is concluded from these results that carpaine affects the myocardium directly. The effects of carpaine may be related to its macrocyclic dilactone structure, a possible cation chelating structure. Carpaine is found in papaya, fruits, and fenugreek.

CAS Number

3463-92-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00082 g/L	ALOGPS
logP	4.48	ALOGPS
logP	5.9	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	134.68 m³·mol⁻¹	ChemAxon
Polarizability	57.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C28H50N2O4

IUPAC name

13,26-dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.2¹¹,¹⁴]triacontane-3,16-dione

InChI Identifier

InChI=1S/C28H50N2O4/c1-21-25-19-17-23(29-21)13-9-5-3-8-12-16-28(32)34-26-20-18-24(30-22(26)2)14-10-6-4-7-11-15-27(31)33-25/h21-26,29-30H,3-20H2,1-2H3

InChI Key

AMSCMASJCYVAIF-UHFFFAOYSA-N

Isomeric SMILES

CC1NC2CCC1OC(=O)CCCCCCCC1CCC(OC(=O)CCCCCCC2)C(C)N1

Average Molecular Weight

478.7076

Monoisotopic Molecular Weight

478.377058098

Classification

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dicarboxylic acid or derivatives
Piperidine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Secondary aliphatic amine
Oxacycle
Secondary amine
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.25%; H 10.53%; N 5.85%; O 13.37%	DFC
Melting Point	Mp 119-120° (117-118.5°)	DFC
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	[a]22230 -240 (c, 0.12 in MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Carpaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1000900000-2e147aee0819e3c44ed9	Spectrum
Predicted GC-MS	Carpaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-8323d3ae9982b07c31d4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000900000-e181407356dc1c703dec	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-0000900000-92a34d38ca3b7371046f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-64470a29cca38899ca21	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-c676af29fb32f314a648	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-0000900000-88f5d6bfc87a72056dff	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-495a2be07010cad79068	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000900000-495a2be07010cad79068	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01t9-0000900000-bb48d2c2ddde2c1a2913	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-fbe34a22d09b1169b0f0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000900000-fbe34a22d09b1169b0f0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-0000900000-0257608f186920216cbc	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10135

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

CFL84-H:CFL84-H

EAFUS ID

Not Available

Dr. Duke ID

CARPAINE

BIGG ID

Not Available

KNApSAcK ID

C00002026

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

Carpaine

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
amebicide	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dysenteric	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardiodepressant	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cardiotonic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
hypotensive			DUKE
paralytic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
protisticide			DUKE
respiradepressant			DUKE
trichuricide			DUKE
vasoconstrictor	50514	Drug used to cause constriction of the blood vessels.	DUKE
vermicide			DUKE