CHEBI:2431 - acremoauxin A

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ChEBI Name acremoauxin A
ChEBI ID CHEBI:2431
Definition An indolyl carboxylate ester obtained by formal condensation of one of the primary hydroxy groups of D-arabinitol with the carboxy group of (2R)-2-(indol-3-yl)propanoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C16H21NO6
Net Charge 0
Average Mass 323.34100
Monoisotopic Mass 323.13689
InChI InChI=1S/C16H21NO6/c1-9(11-6-17-12-5-3-2-4-10(11)12)16(22)23-8-14(20)15(21)13(19)7-18/h2-6,9,13-15,17-21H,7-8H2,1H3/t9-,13-,14-,15-/m1/s1
InChIKey YBXVDDODTFXOHM-SEWBAHNZSA-N
SMILES C[C@@H](C(=O)OC[C@@H](O)[C@H](O)[C@H](O)CO)c1c[nH]c2ccccc12
Metabolite of Species Details
Paecilomyces sp. (NCBI:txid40383) Isolated from cultures of strain CAFT156 See: PubMed
Roles Classification
Biological Role(s): plant growth regulator
A chemical, natural or artificial, that can affect the rate of growth of a plant.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acremoauxin A (CHEBI:2431) has functional parent D-arabinitol (CHEBI:18333)
acremoauxin A (CHEBI:2431) has role fungal metabolite (CHEBI:76946)
acremoauxin A (CHEBI:2431) has role plant growth regulator (CHEBI:26155)
acremoauxin A (CHEBI:2431) has role plant metabolite (CHEBI:76924)
acremoauxin A (CHEBI:2431) is a indolyl carboxylate ester (CHEBI:46939)
acremoauxin A (CHEBI:2431) is a pentitol derivative (CHEBI:63434)
IUPAC Name
(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl (2R)-2-(1H-indol-3-yl)propanoate
Synonyms Sources
2-(3-Indolyl)propanoylmannitol KEGG COMPOUND
Acremoauxin A KEGG COMPOUND
Manual Xrefs Databases
C00001524 KNApSAcK
C08468 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
125537-93-1 CAS Registry Number KEGG COMPOUND
22790054 Reaxys Registry Number Reaxys
Citations
Talontsi FM, Nwemeguela Kenla TJ, Dittrich B, Douanla-Meli C, Laatsch H (2012)
Paeciloside A, a new antimicrobial and cytotoxic polyketide from Paecilomyces sp. strain CAFT156.
Planta medica 78, 1020-1023 [PubMed:22692953]
[show Abstract]
Richter JM, Whitefield BW, Maimone TJ, Lin DW, Castroviejo MP, Baran PS (2007)
Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: total synthesis of acremoauxin A and oxazinin 3.
Journal of the American Chemical Society 129, 12857-12869 [PubMed:17900115]
[show Abstract]
Last Modified
29 January 2015