Classification Term: 106

Pyrrolines (ontology term: CHEMONTID:0000091)

Compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms." []

found 18 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

Child Taxonomies: Pyrroline carboxylic acids and derivatives, Phenylpyrrolines

1-Pyrroline-2-carboxylic acid

3,4-dihydro-2H-pyrrole-5-carboxylic acid

C5H7NO2 (113.0477)


1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate. [HMDB] 1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate.

   

1-Pyrroline-4-hydroxy-2-carboxylate

4-hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid

C5H7NO3 (129.0426)


Much or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate. Normal human values for endogenous urinary PCA in 16 individuals averaged 0.51 mumol/day, with a range of 0.20-1.3 mumol and a SD of 0.31 mumol. The probable source of human PCA is free hydroxy-L-proline, as inferred from the high value for PCA in the urine of a subject with hereditary hydroxyprolinemia, and from the threeto eightfold elevation in PCA excretion by two normal subjects after a large oral load of hydroxyl-L-proline. (PMID: 4430715). Much or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate.

   

1-Methylpyrrolinium

1-Methyl-delta(1)-pyrrolinium, 2-(14)C-labeled

C5H10N1+ (84.0813)


This compound belongs to the family of Pyrrolines. These are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

   

Tenuazonic acid

3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9ci

C10H15NO3 (197.1052)


Tenuazonic acid is produced by Aspergillus species Causes rice leaf rot Tenuazonic acid is a mycotoxin. It is a toxic secondary metabolite, produced by Alternaria (e. g. Alternaria alternata or Alternaria tenuis) and Phoma species. It inhibits the protein synthesis machinery D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Production by Aspergillus subspecies Causes rice leaf rot D000970 - Antineoplastic Agents

   

1-Pyrroline

3,4-Dihydro-2H-pyrrole

C4H7N (69.0578)


Pyrrolines, also known under the name dihydropyrroles, are three different heterocyclic organic chemical compounds which differ in the position of the double bond. Pyrrolines are formally derived from the aromate pyrrole by hydrogenation. 1-Pyrroline is a cyclic imine while 2-pyrroline and 3-pyrroline are cyclic amines. Present in clam and squid. Flavouring agent for fish products and other foods. 3,4-Dihydro-2H-pyrrole is found in many foods, some of which are garden onion (variety), breadnut tree seed, chinese bayberry, and kiwi.

   

(±)-Rollipyrrole

4-ethenyl-5-{[(2Z)-4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-5-methoxy-3-methyl-2,5-dihydro-1H-pyrrol-2-one

C16H20N2O3 (288.1474)


(±)-Rollipyrrole is found in alcoholic beverages. (±)-Rollipyrrole is a constituent of the leaves of Rollinia mucosa (biriba). Constituent of the leaves of Rollinia mucosa (biriba). (±)-Rollipyrrole is found in alcoholic beverages and fruits.

   

(+)-2,3-Dihydro-3-methyl-1H-pyrrole

3-methyl-2,3-dihydro-1H-pyrrole

C5H9N (83.0735)


(+)-2,3-Dihydro-3-methyl-1H-pyrrole is found in herbs and spices. (+)-2,3-Dihydro-3-methyl-1H-pyrrole is an alkaloid from black pepper (Piper nigrum Piperaceae).

   

(R)-Dihydromaleimide

2H-pyrrole-2,5-diol

C4H5NO2 (99.032)


(R)-Dihydromaleimide is found in pulses. (R)-Dihydromaleimide is an alkaloid from the shoots of dwarf pea (Pisum sativum Alkaloid from the shoots of dwarf pea (Pisum sativum). (R)-Dihydromaleimide is found in pulses and common pea.

   

N-Acetyl-2,3-dihydro-1H-pyrrole

1-(2,3-dihydro-1H-pyrrol-1-yl)ethan-1-one

C6H9NO (111.0684)


N-Acetyl-2,3-dihydro-1H-pyrrole is found in cereals and cereal products. N-Acetyl-2,3-dihydro-1H-pyrrole is a odorous constituent of cooked rice and of pandan rampeh (Pandanus amaryllifolius

   

BOX B

2-[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]acetamide

C9H10N2O2 (178.0742)


BOX B is produced by bilirubin oxidation, a heme-derived compound. BOXes are produced as a mixture of isomers, and may be involved in cerebral vasospasm. BOXes are subject of interest in the neurosurgical and neurological fields because of their correlation with and/or role in subarachnoid hemorrhage induced cerebral vasospasm. Subarachnoid hemorrhage (SAH) induces cerebral vasospasm that can lead to ischemic injury or death and is a common complication of SAH. BOX B can be found in cerebrospinal fluid in SAH. (PMID: 17981669) [HMDB] BOX B is produced by bilirubin oxidation, a heme-derived compound. BOXes are produced as a mixture of isomers, and may be involved in cerebral vasospasm. BOXes are subject of interest in the neurosurgical and neurological fields because of their correlation with and/or role in subarachnoid hemorrhage induced cerebral vasospasm. Subarachnoid hemorrhage (SAH) induces cerebral vasospasm that can lead to ischemic injury or death and is a common complication of SAH. BOX B can be found in cerebrospinal fluid in SAH. (PMID: 17981669).

   

BOX A

2-[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]acetamide

C9H10N2O2 (178.0742)


BOX A is produced by bilirubin oxidation, a heme-derived compound. BOXes are produced as a mixture of isomers, and may be involved in cerebral vasospasm. BOXes are subject of interest in the neurosurgical and neurological fields because of their correlation with and/or role in subarachnoid hemorrhage induced cerebral vasospasm. Subarachnoid hemorrhage (SAH) induces cerebral vasospasm that can lead to ischemic injury or death and is a common complication of SAH. BOX A can be found in cerebrospinal fluid in SAH. (PMID: 17981669) [HMDB] BOX A is produced by bilirubin oxidation, a heme-derived compound. BOXes are produced as a mixture of isomers, and may be involved in cerebral vasospasm. BOXes are subject of interest in the neurosurgical and neurological fields because of their correlation with and/or role in subarachnoid hemorrhage induced cerebral vasospasm. Subarachnoid hemorrhage (SAH) induces cerebral vasospasm that can lead to ischemic injury or death and is a common complication of SAH. BOX A can be found in cerebrospinal fluid in SAH. (PMID: 17981669).

   

5-Acetyl-3,4-dihydro-2H-pyrrole

1-​(3,​4-​Dihydro-​2H-​pyrrol-​5-​yl)​ethanone

C6H9NO (111.0684)


Key flavour/aroma component of cooked rice, wheatbread crust, popcorn, sweetcorn and roasted sesame. 5-Acetyl-3,4-dihydro-2H-pyrrole is found in cereals and cereal products. 5-Acetyl-3,4-dihydro-2H-pyrrole is found in cereals and cereal products. Key flavour/aroma component of cooked rice, wheatbread crust, popcorn, sweetcorn and roasted sesam

   

3,4-Dihydro-5-propanoyl-2H-pyrrole

1-(3,4-dihydro-2H-Pyrrol-5-yl)-1-propanone, 9ci

C7H11NO (125.0841)


3,4-Dihydro-5-propanoyl-2H-pyrrole is formed by thermal treatment of proline and glucose mixtures. 3,4-Dihydro-5-propanoyl-2H-pyrrole is a constituent of freshly popped corn arom Formed by thermal treatment of proline and glucose mixtures. Constituent of freshly popped corn aroma

   

Pyrroline

2,3-dihydro-1H-pyrrole

C4H7N (69.0578)


Pyrroline, also known as delta(2)-pyrroline or dihydropyrrole, is a member of the class of compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. Pyrroline is soluble (in water) and a very strong basic compound (based on its pKa). Pyrroline can be found in common pea, which makes pyrroline a potential biomarker for the consumption of this food product.

   

5,5-Dimethyl-1-pyrroline N-oxide

2,2-dimethyl-3,4-dihydro-2H-pyrrol-1-ium-1-olate

C6H11NO (113.0841)


   

5,5-Dimethyl-1-pyrroline

2,2-dimethyl-3,4-dihydro-2H-pyrrole

C6H11N (97.0891)


   

3-Ethyl-5-hydroxy-4,5-dimethyl-pyrrolin-2-one

3-ethyl-5-hydroxy-4,5-dimethyl-2,5-dihydro-1H-pyrrol-2-one

C8H13NO2 (155.0946)


   

Succinimido

(2-oxo-3,4-dihydro-2H-pyrrol-5-yl)oxidanyl

C4H4NO2 (98.0242)