indanomycin (CHEBI:141380)

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CHEBI:141380 - indanomycin

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ChEBI ID	CHEBI:141380
ChEBI Name	indanomycin
Stars
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.
Last Modified	17 August 2023
Submitter	R. Stephan
Downloads	Molfile

Formula	C31H43NO4
Net Charge	0
Average Mass	493.688
Monoisotopic Mass	493.31921
SMILES	[H][C@@]12CC[C@H](CC)[C@@]1([H])C=C[C@@]([H])(/C=C/C=C(\CC)[C@]1([H])O[C@@]([H])([C@@H](C)C(=O)O)CC[C@@H]1C)[C@@]2([H])C(=O)c1cccn1
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

Species of Metabolite	Component	Source	Comments
Streptomyces antibioticus (ncbitaxon:1890)	-	PubMed (374323)	Strain: NRRL 8167

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. 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.
Applications:	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. 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. antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
X-14547A	ChEBI
(−)-X-14547A	ChEBI
antibiotic X 14547A	KNApSAcK

Manual Xrefs	Databases
C00016347	KNApSAcK

Citations