Classification Term: 304

Pyrroloindoles (ontology term: CHEMONTID:0001733)

Compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring." []

found 24 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Indoles and derivatives

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

(-)-Chimonanthine

(3aS,8bS)-8b-[(3aS,8bS)-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indol-8b-yl]-3-methyl-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole

C22H26N4 (346.2157)


(-)-chimonanthine is the (3aS,3aS,8aS,8aS)-stereoisomer of chimonanthine. It is an enantiomer of a (+)-chimonanthine. (-)-Chimonanthine is a natural product found in Eumachia forsteriana, Chimonanthus praecox, and Idiospermum australiense with data available. meso-Chimonanthine is found in herbs and spices. meso-Chimonanthine is an alkaloid from Calycanthus floridus (Carolina allspice

   

Physostigmine

(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; 2-hydroxybenzoic acid

C15H21N3O2 (275.1634)


Physostigmine is a white, odorless, microcrystalline powder. Used as a cholinergic (anticholinesterase) agent and as a veterinary medication. (EPA, 1998) Physostigmine is a carbamate ester and an indole alkaloid. It has a role as a miotic, an EC 3.1.1.8 (cholinesterase) inhibitor and an antidote to curare poisoning. A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. Physostigmine is a natural product found in Streptomyces griseofuscus, Streptomyces, and other organisms with data available. A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. See also: Physostigmine Salicylate (active moiety of). A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. [PubChem] S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AB - Antidotes D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D008916 - Miotics C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor D004791 - Enzyme Inhibitors KEIO_ID E007; [MS2] KO008958 KEIO_ID E007

   

Calycanthidine

1,8-dimethyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

C23H28N4 (360.2314)


Calycanthidine is found in herbs and spices. Calycanthidine is an alkaloid from the seeds of Calycanthus floridus (Carolina allspice

   

Roquefortine

(4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione

C22H23N5O2 (389.1852)


Roquefortine is found in milk and milk products. Roquefortine is a metabolite of Penicillium roquefortii, Penicillium commune, Penicillium cyclopium, Penicillium farinosum and many other Penicillium species Common constituent of blue chees. Roquefortine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58735-64-1 (retrieved 2024-10-11) (CAS RN: 58735-64-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

(-)-Folicanthine

3a-{1,8-dimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1,8-dimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

C24H30N4 (374.247)


(-)-Folicanthine is found in herbs and spices. (-)-Folicanthine is an alkaloid from Calycanthus floridus (Carolina allspice) and Calycanthus occidentalis (Californian allspice

   

Garciduol C

4-(3-benzoyl-2,4-dihydroxy-6-methoxyphenyl)-1,2,5-trihydroxy-9H-xanthen-9-one

C27H18O9 (486.0951)


Garciduol C is found in fruits. Garciduol C is a constituent of the root of Garcinia dulcis (mundu)

   

Alline

2,3,8,8a-Tetrahydro-1-methylpyrrolo[2,3-b]indol-3a(1H)-ol, 9ci

C11H14N2O (190.1106)


Alline is found in onion-family vegetables. Alline is an alkaloid from Chinese chives (Allium odorum) and several other Allium specie

   

cyclic 3-Hydroxymelatonin

1-{3a-hydroxy-5-methoxy-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

C13H16N2O3 (248.1161)


This compound belongs to the family of Pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole.

   

cyclic 6-Hydroxymelatonin

1-{6-hydroxy-5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

C13H14N2O3 (246.1004)


cyclic 6-Hydroxymelatonin is a metabolite of melatonin. Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. (Wikipedia)

   

cyclic Melatonin

1-{5-methoxy-1H,2H,3H,8H-pyrrolo[2,3-b]indol-1-yl}ethan-1-one

C13H14N2O2 (230.1055)


cyclic Melatonin is a metabolite of melatonin. Melatonin Listen/ˌmɛləˈtoʊnɪn/, also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes. In animals, circulating levels of the hormone melatonin vary in a daily cycle, thereby allowing the entrainment of the circadian rhythms of several biological functions. (Wikipedia)

   

Clofazimine glucuronide

(2S,3S,4S,5R)-6-(2-{[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin-2-ylidene]amino}propoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

C33H30Cl2N4O7 (664.1491)


Clofazimine glucuronide is a metabolite of clofazimine. Clofazimine is a fat-soluble riminophenazine dye used in combination with rifampicin and dapsone as multidrug therapy (MDT) for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients and Mycobacterium avium paratuberculosis infection in Crohns disease patients. (Wikipedia)

   

Dimethylphysostigmine

1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N,N-dimethylcarbamate

C16H23N3O2 (289.179)


   

(+)-Eseroline

Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS-cis)-

C13H18N2O (218.1419)


   

Posiphen

1-({1,3a,8-trimethyl-1H,2H,3H,3ah,8H,8ah-pyrrolo[2,3-b]indol-5-yl}oxy)-N-phenylmethanimidate

C20H23N3O2 (337.179)


D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors D004791 - Enzyme Inhibitors

   

Antibiotic CC 1065

Benzo(1,2-b:4,3-b)dipyrrole-3(2H)-carboxamide, 7-((1,6-dihydro-4-hydroxy-5-methoxy-7-((4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa(c)pyrrolo(3,2-e)indol-2(1H)-yl)carbonyl)benzo(1,2-b:4,3-b)dipyrrol-3(2H)-yl)carbonyl)-1,6-dihydro-4-hydroxy-5-methox

C37H33N7O8 (703.239)


   

Bizelesin

1,3-bis({2-[1-(chloromethyl)-5-hydroxy-8-methyl-1H,2H,3H,6H-pyrrolo[3,2-e]indole-3-carbonyl]-1H-indol-5-yl})urea

C43H36Cl2N8O5 (814.2186)


   

Carzelesin

2-Benzofurancarboxamide, N-(2-((1-(chloromethyl)-1,6-dihydro-8-methyl-5-(((phenylamino)carbonyl)oxy)benzo(1,2-b:4,3-b)dipyrrol-3(2H)-yl)carbonyl)-1H-indol-5-yl)-6-(diethylamino)-, (S)-

C41H37ClN6O5 (728.2514)


   

Cyclopropylpyrroloindole

2-cyclopropylpyrrolo[2,3-g]indole

C13H10N2 (194.0844)


   

4-Isopropylphenserine

1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-[4-(propan-2-yl)phenyl]carbamate

C23H29N3O2 (379.226)


   

Eptastigmine

1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl heptylcarbamate

C21H33N3O2 (359.2573)


   

Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 3,6,7,8-tetrahydro-6-(aminocarbonyl)-5-hydroxy-4-methoxy-

Benzo(1,2-b:4,3-b)dipyrrole-2-carboxylic acid, 3,6,7,8-tetrahydro-6-(aminocarbonyl)-5-hydroxy-4-methoxy-

C13H13N3O5 (291.0855)


   

Quilostigmine

1,3a,8-Trimethyl-1H,2H,3H,3ah,8H,8ah-pyrrolo[2,3-b]indol-5-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid

C23H27N3O2 (377.2103)


   

Sporidesmin

6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C18H20ClN3O6S2 (473.0482)


   

Leptosine

37-hydroxy-7-(hydroxymethyl)-6,36-dimethyl-30-(propan-2-yl)-3-oxa-31,32,33,34-tetrathia-6,9,11,26,28,36-hexaazadecacyclo[28.4.2.1⁴,¹⁸.0¹,²⁸.0²,¹⁹.0⁴,⁹.0¹⁰,¹⁸.0¹²,¹⁷.0¹⁹,²⁷.0²⁰,²⁵]heptatriaconta-12,14,16,20,22,24-hexaene-5,8,29,35-tetrone

C32H32N6O7S4 (740.1215)


Leptosine, also known as leptosin j, is a member of the class of compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Leptosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leptosine can be found in american cranberry, which makes leptosine a potential biomarker for the consumption of this food product.