23291-96-5
Chemical Structure
Dehydromonocrotaline
Synonym(s): Monocrotaline pyrrole; MCTP; 3,8-Didehydromonocrotaline
- CAS No.: 23291-96-5
- Formula:C16H21NO6
- Molecular Weight:323.34
IUPAC Name: (3R,4R,5R,13aR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,12,13,13a-hexahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
InChIKey: ZONSVLURFASOJK-LLAGZRPASA-N
SMILES: O=C1O[C@@]2([H])C3=C(COC([C@](O)([C@](O)([C@H]1C)C)C)=O)C=CN3CC2
Biological Activity: Dehydromonocrotaline is a mitochondrial respiratory chain complex I NADH oxidase inhibitor, with a IC50 of 62.06 μM and a Ki of 8.1 μM in rats. Dehydromonocrotaline exerts non-competitive inhibitory effects by modifying cysteine thiol groups on complex I, and does not bind to the NADH-binding site. Dehydromonocrotaline dissipates mitochondrial membrane potential and reduces ATP levels. Dehydromonocrotaline can be used in studies related to hepatotoxicity, pulmonary hypertension and liver tumors[1][2][3].
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Dehydromonocrotaline | Dehydromonocrotaline is a mitochondrial respiratory chain complex I NADH oxidase inhibitor, with a IC50 of 62.06 μM and a Ki of 8.1 μM in rats. Dehydromonocrotaline exerts non-competitive inhibitory effects by modifying cysteine thiol groups on complex I, and does not bind to the NADH-binding site. Dehydromonocrotaline dissipates mitochondrial membrane potential and reduces ATP levels. Dehydromonocrotaline can be used in studies related to hepatotoxicity, pulmonary hypertension and liver tumors. | |||||||||||||||||||||
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- [1]. Mingatto FE, et al. Dehydromonocrotaline inhibits mitochondrial complex I. A potential mechanism accounting for hepatotoxicity of monocrotaline. Toxicon. 2007;50(5):724-730. [Content Brief]
- [2]. Okada M, et al. A dehydromonocrotaline-induced pulmonary hypertension model in the beagle. J Thorac Cardiovasc Surg. 1995 Aug;110(2):546-7. [Content Brief]
- [3]. Wang YP, et al. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. Int J Environ Res Public Health. 2005;2(1):74-79. [Content Brief]
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