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Substrate Report for: Methyl-3-hydroxyhexadecanoate

3-hydroxy Palmitic acid methyl ester (3-hydroxy PAME) is an esterized long-chain fatty acid involved in quorum sensing in R. solanacearum, a bacteria that causes lethal wilting in plants. 3-hydroxy-PAME (175 nM) increases levels of PhcA-regulated virulence factors, greater than 20-, 30-, and 25-fold for EPS I, EGL, and PME, respectively, in the AW1-83 strain of R. solanacearum


General
Type Fatty acid ester, Hexadecanoate, Palmitate
Chemical_Nomenclature methyl 3-hydroxyhexadecanoate
Canonical SMILES CCCCCCCCCCCCCC(CC(=O)OC)O
InChI InChI=1S/C17H34O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-16(18)15-17(19)20-2/h16,18H,3-15H2,1-2H3
InChIKey YBTWUESFQWFDMR-UHFFFAOYSA-N
Other name(s) Methyl 3-hydroxypalmitate ; 3-hydroxyhexadecanoic acid methyl ester ; 3-hydroxypalmitic acid methyl ester ; 3-Hydroxy-palmitic acid methyl ester ; 3-hydroxy PAME ; 3-OH PAME ; 3OH PAME ; 3-hydroxy PA methyl ester
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MW|286.45
Formula|C17H34O3
CAS_number|51883-36-4
PubChem|103553
UniChem|YBTWUESFQWFDMR-UHFFFAOYSA-N
IUPHAR|
Wikipedia|

Target
Families | Methyl-3-hydroxyhexadecanoate ligand of proteins in family: 6_AlphaBeta_hydrolase
Protein | 9zzzz-a0a223he11, 9zzzz-a0a223heg6, 9zzzz-a0a223he13

References:
Search PubMed for references concerning: Methyl-3-hydroxyhexadecanoate
    Title: Soil metagenome-derived 3-hydroxypalmitic acid methyl ester hydrolases suppress extracellular polysaccharide production in Ralstonia solanacearum
    Lee MH, Khan R, Tao W, Choi K, Lee SY, Lee JW, Hwang EC, Lee SW
    Ref: J Biotechnol, 270:30, 2018 : PubMed

            

    Title: Characterization of bacteria degrading 3-hydroxy palmitic acid methyl ester (3OH-PAME), a quorum sensing molecule of Ralstonia solanacearum
    Achari GA, Ramesh R
    Ref: Lett Appl Microbiol, 60:447, 2015 : PubMed

            

    Title: Identification of 3-hydroxypalmitic acid methyl ester as a novel autoregulator controlling virulence in Ralstonia solanacearum
    Flavier AB, Clough SJ, Schell MA, Denny TP
    Ref: Molecular Microbiology, 26:251, 1997 : PubMed