Carpaine

Catalog Number	ACM3463921
CAS Number	3463-92-1
Structure
Synonyms	(1S,11R,13S,14S,24R,26S)-13,26-Dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione
Molecular Weight	478.7
InChI	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/t21-,22-,23+,24+,25-,26-/m0/s1
InChI Key	AMSCMASJCYVAIF-QCVMBYIASA-N
Melting Point	119-120 °C
Purity	95%+
Complexity	561
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	6
Exact Mass	478.37705808
Heavy Atom Count	34
Hydrogen Bond Acceptor Count	6
Hydrogen Bond Donor Count	2
Isomeric SMILES	C[C@H]1[C@@H]2CC[C@H](N1)CCCCCCCC(=O)O[C@H]3CC[C@@H](CCCCCCCC(=O)O2)N[C@H]3C
Monoisotopic Mass	478.37705808
PhysicalState	Powder
Rotatable Bond Count	0
Topological Polar Surface Area	76.7 Ų

Case Study

Evaluations of in Vitro Antimalarial Effects and Cytotoxicity of Carpaine

Teng W C, et al. Natural Product Communications, 2019, 14(1), 1934578X1901400110.

Carpaine is an active substance isolated from C. papaya leaves, and it is expected to be further developed as an antimalarial lead compound.. To evaluate the antimalarial effects of carpain, a series of investigations were conducted, including cytotoxicity, hemolysis, and other pharmacological activity assessments.
· Cytotoxicity and selectivity: A cytotoxicity study was conducted to assess the selectivity of samples that have antiplasmodial activity. The results suggest that the antimalarial activity of carpaine may be due to a direct inhibitory effect on the parasite rather than non-selective toxicity to the host and target cells.
· Haemolysis evaluation: Based on the results of the hemolysis assessment, the anti-Plasmodium activity of carpaine is not due to erythrocyte lysis but is a real inhibitory effect on Plasmodium parasites.
· Other pharmacological activities: In animal models, Carpaine has been shown to have antithrombocytopenic effects, improve hemodynamic response, reduce blood pressure, induce smooth muscle relaxation, and exhibit antimicrobial properties.

The Protective Mechanism of Carpaine on H9c2 Cardiomyocytes

Sudi S, et al. Pharmaceuticals, 2022, 15(2), 230.

Carpaine has a protective effect on embryonic cardiomyocytes of the H9c2 cell line. To elucidate this protective effect, cytotoxicity and proliferation assays, immunoblot analysis, wound healing assay, and mitochondrial membrane potential (MMP) assessment of H9c2 cells after carpaine treatment were performed. Results indicate that carpaine positively regulates cardiomyocyte repair by increasing proliferation rate through FAK/AKT and FAK/ERK1/2-dependent pathways.
Action mechanism of carpaine
· Carpaine promotes H9c2 cell proliferation: Treatment with 1 µM carpaine significantly increased H9c2 cell proliferation after 24 and 48 hours of incubation.
· Following upstream FAK activation, carpaine promotes cardiomyocyte proliferation through the ERK1/2 and AKT signaling pathways.
· Carpaine exerts protective effects by enhancing wound healing through cardiomyocyte proliferation in response to ischemia/reperfusion injury (IRI).
· Carpaine significantly improved the recovery of MMP after oxidative stress induced by H2O2 treatment, which means that Carpaine provides H9c2 cells with protection against H2O2-induced oxidative stress.

Custom Q&A

What is the product name of the chemical compound with the CAS number 3463-92-1?

The product name is carpaine.

What are some synonyms for carpaine?

Some synonyms for carpaine are 13,26-Dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione and (1S,11R,13S,14S,24R,26S)-13,26-Dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione.

What is the molecular formula of carpaine?

The molecular formula is C28H50N2O4.

What is the molecular weight of carpaine?

The molecular weight is 478.71 g/mol.

What is the melting point of carpaine?

The melting point is 119-120°C.

In which solvent is carpaine most soluble?

Carpaine is most soluble in chloroform, with a solubility of 10 mg/ml.

What is the predicted pka value of carpaine?

The predicted pka value is 9±0.60.

What are the storage conditions recommended for carpaine?

It is recommended to store carpaine at -20°C.

What are some potential uses of carpaine?

Carpaine has been shown to exhibit cardiovascular effects and is a major component of papaya leaves.

What is the refractive index of carpaine?

The estimated refractive index is 1.5800.

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