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

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	An agent that kills or inhibits the growth of amoebas, used to treat amoebic infections such as amoebic dysentery and liver abscess, commonly targeting Entamoeba histolytica.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti dysenteric	52217	An agent that treats and prevents dysentery, reducing inflammation and diarrhea. It is used to manage bacterial, viral, or parasitic infections, and is commonly applied in treating gastrointestinal disorders, such as amoebic dysentery, and other intestinal infections.	DUKE
Anti-tubercular	33282	An agent that combats tuberculosis, playing a biological role in inhibiting the growth of Mycobacterium tuberculosis. Therapeutically, it is used to treat and prevent tuberculosis, with key medical applications including the treatment of active TB, latent TB, and TB meningitis, as well as preventing the spread of TB in high-risk populations.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cardiodepressant	38070	An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.	DUKE
Cardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.	DUKE
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Paralytic		An agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Protisticide		An agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.	DUKE
Respiradepressant		An agent that suppresses gas exchange, leading to increased carbon dioxide levels and respiratory acidosis, characteristic of hypoventilation, often used with caution in managing severe pain or anesthesia, but can have adverse effects if misused.	DUKE
Trichuricide		An agent that kills parasitic whipworms of the genus Trichuris, used to treat trichuriasis, a parasitic infection affecting the large intestine, and other related gastrointestinal disorders.	DUKE
Vasoconstrictor	50514	An agent that narrows blood vessels, reducing blood flow. It plays a biological role in regulating blood pressure and is therapeutically used to treat conditions like hypotension, nasal congestion, and bleeding. Key medical uses include managing shock, reducing bleeding during surgery, and relieving migraine headaches.	DUKE
Vermicide		An agent that kills worms, playing a biological role in parasite control. Therapeutically, it is used to treat worm infestations, with key medical applications including the treatment of intestinal worms, hookworms, and other parasitic infections.	DUKE