Page last updated: 2024-10-15

undecylprodigiosin

Description

prodigiosin 25C: red pigment produced by Streptomyces hiroshimensis; potent immunosuppressive agent with its primary effect on functions of T cells; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

undecylprodigiosin : A member of the class of tripyrroles that is 1H-pyrrole substituted by (4'-methoxy-1H,5'H-[2,2'-bipyrrol]-5'-ylidene)methyl and undecyl groups at positions 2 and 5, respectively. It is a pigment produced by Stveptomyces coelicolor. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135515151
CHEBI ID29702
SCHEMBL ID20473780
SCHEMBL ID20473782
SCHEMBL ID22510569
MeSH IDM0136797

Synonyms (26)

Synonym
1h-pyrrole, 2-((3-methoxy-5-(1h-pyrrol-2-yl)-2h-pyrrol-2-ylidene)methyl)-5-undecyl-
prodigiosin 25c
undecylprodigiosin
undecylprodiginine
(2z,5z)-3-methoxy-5-pyrrol-2-ylidene-2-[(5-undecyl-1h-pyrrol-2-yl)methylidene]pyrrole
unii-zq2hk5e6zg
52340-48-4
zq2hk5e6zg ,
prodigiosin-25 c
undecylprodiginin
(5'z)-4'-methoxy-5'-[(5-undecyl-1h-pyrrol-2-yl)methylidene]-1h,5'h-2,2'-bipyrrole
CHEBI:29702
13129-81-2
OGBPBDMDXNFPCS-DYTRJAOYSA-N
2,2'-bi-1h-pyrrole, 4-methoxy-5-[(5-undecyl-2h-pyrrol-2-ylidene)methyl]-
2,2'-bipyrrole, 4-methoxy-5-[(5-undecyl-2h-pyrrol-2-ylidene)methyl]-
2-[(z)-[3-methoxy-5-(1h-pyrrol-2-yl)-2h-pyrrol-2-ylidene]methyl]-5-undecyl-1h-pyrrole
SCHEMBL20473780
SCHEMBL20473782
EX-A7586
(2z)-3-methoxy-5-(1h-pyrrol-2-yl)-2-[(5-undecyl-1h-pyrrol-2-yl)methylidene]pyrrole
SCHEMBL22510569
DTXSID001315967
1h-pyrrole, 2-[(z)-[3-methoxy-5-(1h-pyrrol-2-yl)-2h-pyrrol-2-ylidene]methyl]-5-undecyl-
2-(5-undecyl-2-pyrrolylmethylene)-3-methoxy-5-(2-pyrrolyl)-2h-pyrrole
AKOS040746444

Research Excerpts

Overview

Undecylprodigiosin (UP) is a bacterial bioactive metabolite produced by Streptomyces and Serratia.

ExcerptReference
"Undecylprodigiosin (UP) is a bacterial bioactive metabolite produced by Streptomyces and Serratia. "( Undecylprodigiosin selectively induces apoptosis in human breast carcinoma cells independent of p53.
Chang, CC; Chang, JS; Cheuh, PJ; Ho, TF; Ko, JL; Lai, JK; Liu, FS; Lu, CH; Ma, CJ; Tang, PC; Tsai Chang, J; Tsai, YT; Wei, YH; Yeh, CT; Yen, HE, 2007
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
radiosensitizing agentA drug that makes increases the sensitivity of tumour cells to radiation therapy.
immunosuppressive agentAn agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
biological pigmentAn endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
tripyrrole
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (125)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (1.60)18.7374
1990's32 (25.60)18.2507
2000's42 (33.60)29.6817
2010's43 (34.40)24.3611
2020's6 (4.80)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (3.97%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other121 (96.03%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]