CHEBI:141380 - indanomycin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name indanomycin
ChEBI ID CHEBI:141380
Definition An indene that is (3aS,7aR)-2,3,3a,4,5,7a-hexahydro-1H-indene which is substituted at the 2-pro-R position by a 1H-pyrrol-2-ylcarbonyl group, at the 9-pro-S position by an ethyl group, and at the 5-pro-R position by a hexa-1,3-dineyl group in which position 4 has been substituted by a (2R,3S,6R)-6-[(1R)-1-carboxyethyl]-3-methyltetrahydropyran-2-yl group. It exhibits activity against Gram-positive bacteria as well as antihypertensive and antitumour. It also functions as an effective growth promoter for ruminants.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C31H43NO4
Net Charge 0
Average Mass 493.679
Monoisotopic Mass 493.31921
InChI InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1
InChIKey BAIPOTOKPGDCHA-MWBHXQFBSA-N
SMILES C1[C@@H]([C@@](O[C@](C1)([C@H](C(O)=O)C)[H])(/C(=C/C=C/[C@]2([C@]([C@@]3([H])[C@@](C=C2)([H])[C@H](CC3)CC)(C(C4=CC=CN4)=O)[H])[H])/CC)[H])C
Metabolite of Species Details
Streptomyces antibioticus (NCBI:txid1890) of strain NRRL 8167 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
ionophore
A compound which can carry specific ions through membranes of cells or organelles.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
animal growth promotant
Substances that are administered to farmed animals to improve productivity by promoting weight gain, increasing muscle mass, limiting fat deposition, reducing feed consumption, and reducing waste production.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing indanomycin (CHEBI:141380) has role animal growth promotant (CHEBI:82655)
indanomycin (CHEBI:141380) has role antibacterial agent (CHEBI:33282)
indanomycin (CHEBI:141380) has role antihypertensive agent (CHEBI:35674)
indanomycin (CHEBI:141380) has role antineoplastic agent (CHEBI:35610)
indanomycin (CHEBI:141380) has role bacterial metabolite (CHEBI:76969)
indanomycin (CHEBI:141380) has role insecticide (CHEBI:24852)
indanomycin (CHEBI:141380) has role ionophore (CHEBI:24869)
indanomycin (CHEBI:141380) is a aromatic ketone (CHEBI:76224)
indanomycin (CHEBI:141380) is a indene (CHEBI:37910)
indanomycin (CHEBI:141380) is a monocarboxylic acid (CHEBI:25384)
indanomycin (CHEBI:141380) is a oxanes (CHEBI:46942)
IUPAC Name
(2R)-2-[(2R,5S,6R)-6-{(3E,5E)-6-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(1H-pyrrol-2-ylcarbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hexa-3,5-dien-3-yl}-5-methyltetrahydro-2H-pyran-2-yl]propanoic acid
Synonyms Sources
(−)-X-14547A ChEBI
antibiotic X 14547A KNApSAcK
X-14547A ChEBI
Manual Xref Database
C00016347 KNApSAcK
View more database links
Citations Waiting for Citations Types Sources
19072095 PubMed citation Europe PMC
19301315 PubMed citation Europe PMC
21491871 PubMed citation Europe PMC
23180592 PubMed citation Europe PMC
374323 PubMed citation SUBMITTER
374324 PubMed citation Europe PMC
9711253 PubMed citation Europe PMC
Last Modified
17 August 2023