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Record Information
Version2.0
Created at2020-12-09 02:11:11 UTC
Updated at2021-07-15 16:50:06 UTC
NP-MRD IDNP0004766
Secondary Accession NumbersNone
Natural Product Identification
Common NameAutoinducer I
Provided ByNPAtlasNPAtlas Logo
DescriptionN-(3-oxohexanoyl)-L-homoserine lactone is also known as (S)-3-(3-ketohexanamido)-2-oxotetrahydrofuran or (S)-3-(3-ketohexanamido)butyrolactone. Autoinducer I is found in Azospirillum lipoferum, Erwinia and Pectobacterium carotovorum. Autoinducer I was first documented in 1992 (PMID: 1335238). Based on a literature review a small amount of articles have been published on N-(3-oxohexanoyl)-L-homoserine lactone (PMID: 34413838) (PMID: 33321169) (PMID: 32717872) (PMID: 32457732).
Structure
Data?1624574203
Synonyms
Chemical FormulaC10H15NO4
Average Mass213.2330 Da
Monoisotopic Mass213.10011 Da
IUPAC Name3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide
Traditional Name3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide
CAS Registry NumberNot Available
SMILES
CCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChI Identifier
InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1
InChI KeyYRYOXRMDHALAFL-QMMMGPOBSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Azospirillum lipoferumLOTUS Database
ErwiniaNPAtlas
Erwinia carotovoraLOTUS Database
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.09ALOGPS
logP0.28ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.98 m³·mol⁻¹ChemAxon
Polarizability21.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA003620
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID599950
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID63789
Good Scents IDNot Available
References
General References
  1. Bainton NJ, Stead P, Chhabra SR, Bycroft BW, Salmond GP, Stewart GS, Williams P: N-(3-oxohexanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem J. 1992 Dec 15;288 ( Pt 3):997-1004. doi: 10.1042/bj2880997. [PubMed:1335238 ]
  2. Zhang W, Fan X, Li J, Ye T, Mishra S, Zhang L, Chen S: Exploration of the Quorum-Quenching Mechanism in Pseudomonas nitroreducens W-7 and Its Potential to Attenuate the Virulence of Dickeya zeae EC1. Front Microbiol. 2021 Aug 3;12:694161. doi: 10.3389/fmicb.2021.694161. eCollection 2021. [PubMed:34413838 ]
  3. Molnar M, Fenyvesi E, Berkl Z, Nemeth I, Fekete-Kertesz I, Marton R, Vaszita E, Varga E, Ujj D, Szente L: Cyclodextrin-mediated quorum quenching in the Aliivibrio fischeri bioluminescence model system - Modulation of bacterial communication. Int J Pharm. 2021 Feb 1;594:120150. doi: 10.1016/j.ijpharm.2020.120150. Epub 2020 Dec 13. [PubMed:33321169 ]
  4. Zhang W, Luo Q, Zhang Y, Fan X, Ye T, Mishra S, Bhatt P, Zhang L, Chen S: Quorum Quenching in a Novel Acinetobacter sp. XN-10 Bacterial Strain against Pectobacterium carotovorum subsp. carotovorum. Microorganisms. 2020 Jul 23;8(8). pii: microorganisms8081100. doi: 10.3390/microorganisms8081100. [PubMed:32717872 ]
  5. Fan X, Ye T, Li Q, Bhatt P, Zhang L, Chen S: Potential of a Quorum Quenching Bacteria Isolate Ochrobactrum intermedium D-2 Against Soft Rot Pathogen Pectobacterium carotovorum subsp. carotovorum. Front Microbiol. 2020 May 8;11:898. doi: 10.3389/fmicb.2020.00898. eCollection 2020. [PubMed:32457732 ]