Classification Term: 334

Pyrrolizines (ontology term: CHEMONTID:0000219)

Compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring." []

found 25 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

Child Taxonomies: There is no child term of current ontology term.

Monocrotaline

5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadec-10-ene-3,7-dione

C16H23NO6 (325.1525298)


Hepatotoxin. Causative agent of much seneciosis, e.g. accidental poisoning by S. by weed residues in bread, and characterised by venoocculosive disease Hepatotoxin. Causative agent of much seneciosis, e.g. accidental poisoning by S. by weed residues in bread, and characterised by venoocculosive diseas CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2249 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 131 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 121 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 151 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 141 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 111 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 161 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 171 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 101 Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8]. Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8].

   

Olitorin

7,11-dihydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

C35H52O14 (696.3356891999999)


Isolated from Corchorus olitorius (Jews mallow). Olitorin is found in tea, herbs and spices, and green vegetables. Olitorin is found in green vegetables. Olitorin is isolated from Corchorus olitorius (Jews mallow D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides

   

1-(2,3-Dihydro-6-methyl-1H-pyrrolizin-5-yl)-1,4-pentanedione

1-(2-methyl-6,7-dihydro-5H-pyrrolizin-3-yl)pentane-1,4-dione

C13H17NO2 (219.12592220000002)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-6-methyl-5-(5-methyl-2-furanyl)-1H-pyrrolizine

2,3-Dihydro-6-methyl-5-(5-methyl-2-furanyl)-1H-pyrrolizine

C13H15NO (201.115358)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-1H-pyrrolizine-5-carboxaldehyde

2,3-Dihydro-1H-pyrrolizine-5-carboxaldehyde

C8H9NO (135.0684104)


Proline-derived Maillard product. Proline-derived Maillard product

   

1-(2,3-Dihydro-6,7-dimethyl-1H-pyrrolizin-5-yl)-2-hydroxy-1-propanone

1-(6,7-dimethyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-hydroxypropan-1-one

C12H17NO2 (207.12592220000002)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-5-(5-methyl-2-furanyl)-1H-pyrrolizine

5-(5-methylfuran-2-yl)-2,3-dihydro-1H-pyrrolizine

C12H13NO (187.0997088)


Proline-derived Maillard product. Proline-derived Maillard product

   

1-(2,3-Dihydro-1H-pyrrolizin-5-yl)-1-butanone

1-(6,7-dihydro-5H-pyrrolizin-3-yl)butan-1-one

C11H15NO (177.115358)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-7-methyl-5-propanoyl-1H-pyrrolizine

1-(7-methyl-2,3-dihydro-1H-pyrrolizin-5-yl)propan-1-one

C11H15NO (177.115358)


Proline- or lysine-derived Maillard product. Proline- or lysine-derived Maillard product

   

2,3-Dihydro-6-methyl-5-propanoyl-1H-pyrrolizine

1-(6-methyl-2,3-dihydro-1H-pyrrolizin-5-yl)propan-1-one

C11H15NO (177.115358)


Proline-derived Maillard product. Proline-derived Maillard product

   

1-(2,3-Dihydro-5-ethyl-1H-pyrrolizin-7-yl)ethanone

1-(5-ethyl-2,3-dihydro-1H-pyrrolizin-7-yl)ethan-1-one

C11H15NO (177.115358)


Proline-derived Maillard product. Proline-derived Maillard product

   

5-Acetyl-2,3-dihydro-6,7-dimethyl-1H-pyrrolizine

1-(6,7-dimethyl-2,3-dihydro-1H-pyrrolizin-5-yl)ethan-1-one

C11H15NO (177.115358)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-5-(3-hydroxypropanoyl)-1H-pyrrolizine

1-(2,3-dihydro-1H-Pyrrolizin-5-yl)-3-hydroxy-1-propanone

C10H13NO2 (179.09462380000002)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-5-propanoyl-1H-pyrrolizine

1-(2,3-dihydro-1H-pyrrolizin-5-yl)propan-1-one

C10H13NO (163.0997088)


Proline-derived Maillard product. Proline-derived Maillard product

   

5-Acetyl-2,3-dihydro-7-methyl-1H-pyrrolizine

1-(7-methyl-2,3-dihydro-1H-pyrrolizin-5-yl)ethan-1-one

C10H13NO (163.0997088)


Proline- or lysine-derived Maillard product. Proline- or lysine-derived Maillard product

   

5-Acetyl-2,3-dihydro-6-methyl-1H-pyrrolizine

1-(2,3-dihydro-6-Methyl-1H-pyrrolizin-5-yl)ethanone, 9ci

C10H13NO (163.0997088)


5-Acetyl-2,3-dihydro-6-methyl-1H-pyrrolizine is found in alcoholic beverages. Proline-derived Maillard product. 5-Acetyl-2,3-dihydro-6-methyl-1H-pyrrolizine is a constituent of beer and malt aroma. Proline-derived Maillard product. Constituent of beer and malt aroma. 5-Acetyl-2,3-dihydro-6-methyl-1H-pyrrolizine is found in alcoholic beverages.

   

1-(2,3-Dihydro-5-methyl-1H-pyrrolizin-7-yl)ethanone

1-(5-methyl-2,3-dihydro-1H-pyrrolizin-7-yl)ethan-1-one

C10H13NO (163.0997088)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-5,6-dimethyl-1H-pyrrolizine-7-carboxaldehyde

2,3-Dihydro-5,6-dimethyl-1H-pyrrolizine-7-carboxaldehyde

C10H13NO (163.0997088)


Proline-derived Maillard product. Proline-derived Maillard product

   

1-(2,3-Dihydro-5,6-dimethyl-1H-pyrrolizin-7-yl)ethanone

1-(5,6-dimethyl-2,3-dihydro-1H-pyrrolizin-7-yl)ethan-1-one

C11H15NO (177.115358)


Proline- or lysine-derived Maillard product. Proline- or lysine-derived Maillard product

   

1-(2,3-Dihydro-1H-pyrrolizin-5-yl)-2-propen-1-one

1-(2,3-Dihydro-1H-pyrrolizin-5-yl)-2-propen-1-one

C10H11NO (161.0840596)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-5-methyl-1H-pyrrolizine-7-carboxaldehyde

2,3-Dihydro-5-methyl-1H-pyrrolizine-7-carboxaldehyde

C9H11NO (149.0840596)


Proline-derived Maillard product. Proline-derived Maillard product

   

1-(2,3-Dihydro-1H-pyrrolizin-5-yl)-1,4-pentanedione

1-(2,3-Dihydro-1H-pyrrolizin-5-yl)-1,4-pentanedione

C12H15NO2 (205.110273)


Proline-derived Maillard product. Proline-derived Maillard product

   

2,3-Dihydro-6-methyl-1H-pyrrolizine-5-carboxaldehyde

2,3-Dihydro-6-methyl-1H-pyrrolizine-5-carboxaldehyde

C9H11NO (149.0840596)


2,3-Dihydro-6-methyl-1H-pyrrolizine-5-carboxaldehyde is found in alcoholic beverages. Proline-derived Maillard product. 2,3-Dihydro-6-methyl-1H-pyrrolizine-5-carboxaldehyde is a volatile constituent of beer and cooked asparagus. Proline-derived Maillard product. Volatile constituent of beer and cooked asparagus. 2,3-Dihydro-6-methyl-1H-pyrrolizine-5-carboxaldehyde is found in alcoholic beverages and green vegetables.

   

5-Acetyl-2,3-dihydro-1H-pyrrolizine

1-(2,3-dihydro-1H-Pyrrolizin-5-yl)ethanone, 9ci

C9H11NO (149.0840596)


Proline-derived Maillard product. Constituent of popcorn, beer and cooked asparagus aroma. 5-Acetyl-2,3-dihydro-1H-pyrrolizine is found in alcoholic beverages, cereals and cereal products, and green vegetables. 5-Acetyl-2,3-dihydro-1H-pyrrolizine is found in alcoholic beverages. Proline-derived Maillard product. 5-Acetyl-2,3-dihydro-1H-pyrrolizine is a constituent of popcorn, beer and cooked asparagus aroma.

   

Dehydromonocrotaline

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

C16H21NO6 (323.13688060000004)