Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2018-01-23 18:50:28 UTC
Primary IDFDB002103
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCarpaine
DescriptionAlkaloid 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 Number3463-92-1
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
logP4.48ALOGPS
logP5.9ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity134.68 m³·mol⁻¹ChemAxon
Polarizability57.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H50N2O4
IUPAC name13,26-dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.2¹¹,¹⁴]triacontane-3,16-dione
InChI IdentifierInChI=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 KeyAMSCMASJCYVAIF-UHFFFAOYSA-N
Isomeric SMILESCC1NC2CCC1OC(=O)CCCCCCCC1CCC(OC(=O)CCCCCCC2)C(C)N1
Average Molecular Weight478.7076
Monoisotopic Molecular Weight478.377058098
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides 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 FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.25%; H 10.53%; N 5.85%; O 13.37%DFC
Melting PointMp 119-120° (117-118.5°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22230 -240 (c, 0.12 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1000900000-2e147aee0819e3c44ed9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-8323d3ae9982b07c31d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000900000-e181407356dc1c703decView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0000900000-92a34d38ca3b7371046fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-64470a29cca38899ca21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-c676af29fb32f314a648View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-0000900000-88f5d6bfc87a72056dffView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10135
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) IDCFL84-H:CFL84-H
EAFUS IDNot Available
Dr. Duke IDCARPAINE
BIGG IDNot Available
KNApSAcK IDC00002026
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCarpaine
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
amebicide33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti dysenteric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiodepressant38070 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
cardiotonic38070 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 depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hypotensiveDUKE
paralyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
protisticideDUKE
respiradepressantDUKE
trichuricideDUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
vermicideDUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.