tilivalline profile

tilivalline: a pyrrolo(1,4)benzodiazepine derivative with an 11-beta-indole substituent; found in secondary metabolites of Klebsiella pneumoniae var. oxytoca; structure given in first source; RN given refers to (11S-cis)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tilivalline : A pyrrolobenzodiazepine that is (11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine substituted by an oxo group at position 5, by a hydroxy group at position 9, and by a 1H-indol-3-yl group at position 11S. It is a natural product discovered in Klebsiella oxytoca which is the causative toxin in antibiotic associated hemorrhagic colitis. It exhibits a microtubule-stabilizing activity that leads to mitotic arrest in the host cells. [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]

ID Source	ID
PubMed CID	128363
CHEBI ID	156292
MeSH ID	M0245507

Synonym
epitilivalline
tilivalline
80279-24-9
CHEBI:156292
(7s,8s)-11-hydroxy-8-(1h-indol-3-yl)-3,9-diazatricyclo[8.4.0.0(3,7)]tetradeca-1(10),11,13-trien-2-one
(11s,11as)-9-hydroxy-11-(1h-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
(6s,6as)-4-hydroxy-6-(1h-indol-3-yl)-5,6,6a,7,8,9-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
5h-pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 1,2,3,10,11,11a-hexahydro-9-hydroxy-11(1h-indol-3-yl)-, (11s-cis)-
DTXSID401001138
9-hydroxy-11-(1h-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Role	Description
microtubule-stabilising agent	Any substance that interacts with tubulin to promote polymerisation of microtubules.
toxin	Poisonous substance produced by a biological organism such as a microbe, animal or plant.
bacterial metabolite	Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
[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]

Class	Description
pyrrolobenzodiazepine	Any organic heterotricyclic compound with a skeleton consisting of a pyrrole ring ortho-fused at any position to a benzodiazepine bicyclic system.
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
indole alkaloid	An alkaloid containing an indole skeleton.
indoles	Any compound containing an indole skeleton.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	3 (25.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	8 (66.67)	24.3611
2020's	1 (8.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (8.33%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	11 (91.67%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.17	1	aminobenzoic acid	human metabolite; mouse metabolite
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.21	1	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.31	1	pyrrole; secondary amine
5-methyl-8-hydroxyquinoline 5-methyl-8-hydroxyquinoline: RN given refers to parent cpd; structure in first source & in Negwer, 5th ed, #1202	2.21	1	hydroxyquinoline
tilimycin tilimycin: a pyrrolobenzodiazepine toxin produced by Klebsiella oxytoca which induces apoptosis in epithelial cells and contributes to the development of colitis. tilimycin : A pyrrolobenzodiazepine that is (11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine which is substituted by an oxo group at position 5 and by hydroxy groups at positions 9 and 11. It is an enterotoxic natural product synthesized via a non-ribosomal peptide synthase in Klebsiella oxytoca.	7.31	1	phenols; pyrrolobenzodiazepine	alkylating agent; apoptosis inducer; bacterial metabolite; toxin

Condition	Relationship Strength	Studies
Antibiotic-Associated Colitis [description not available]	3.08	4
Infections, Klebsiella [description not available]	3.23	5
Enterocolitis, Pseudomembranous An acute inflammation of the INTESTINAL MUCOSA that is characterized by the presence of pseudomembranes or plaques in the SMALL INTESTINE (pseudomembranous enteritis) and the LARGE INTESTINE (pseudomembranous colitis). It is commonly associated with antibiotic therapy and CLOSTRIDIUM DIFFICILE colonization.	3.08	4
Klebsiella Infections Infections with bacteria of the genus KLEBSIELLA.	3.23	5
Carcinoma, Epidermoid [description not available]	2.15	1
Cancer of Larynx [description not available]	2.15	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.15	1
Laryngeal Neoplasms Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.	2.15	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	2.1	1
Disease Exacerbation [description not available]	2.11	1
Colitis Gravis [description not available]	2.11	1
Colitis, Granulomatous [description not available]	2.11	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.11	1
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	2.11	1
Leukemia L 1210 [description not available]	2.39	2

tilivalline

Description

Cross-References

Synonyms (10)

Roles (3)

Drug Classes (4)

Research

Studies (12)

Market Indicators

Research Demand Index: 35.38

Study Types