NP-MRD: Showing NP-Card for Autoinducer I (NP0004766)

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Record Information

Version

2.0

Created at

2020-12-09 02:11:11 UTC

Updated at

2021-07-15 16:50:06 UTC

NP-MRD ID

NP0004766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Autoinducer I

Provided By

NPAtlas

Description

N-(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

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118093D          

 30 30  0  0  0  0            999 V2000
    5.1285    1.0749    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -0.0305    0.4422 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8999    0.1740   -0.4237 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0036   -1.0001   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -1.9057    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.0849   -0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4197   -0.5939   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.1911    1.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -0.5950   -0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.1310    0.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6157    0.9589   -0.5395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9384    0.9029    0.1929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0583   -0.4170    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -1.1609    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -2.4007    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.6211    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.6538    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    1.7465   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0234    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.0868    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    1.1278   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    0.2878   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -2.1370   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.5116   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.9303   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.2129    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.6995   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    1.9519   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7861    1.2020   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.5860    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 10  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
M  END

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    5.1285    1.0749    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -0.0305    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    0.1740   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036   -1.0001   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -1.9057    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.0849   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -0.5939   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.1911    1.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -0.5950   -0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.1310    0.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6157    0.9589   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9384    0.9029    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -0.4170    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -1.1609    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -2.4007    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.6211    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.6538    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    1.7465   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0234    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.0868    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    1.1278   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    0.2878   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -2.1370   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.5116   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.9303   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.2129    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.6995   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    1.9519   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7861    1.2020   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.5860    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
M  END

  Mrv1652306242118093D          

 30 30  0  0  0  0            999 V2000
    5.1285    1.0749    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -0.0305    0.4422 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8999    0.1740   -0.4237 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0036   -1.0001   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -1.9057    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.0849   -0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4197   -0.5939   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.1911    1.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -0.5950   -0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.1310    0.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6157    0.9589   -0.5395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9384    0.9029    0.1929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0583   -0.4170    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -1.1609    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -2.4007    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.6211    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.6538    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    1.7465   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0234    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.0868    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    1.1278   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    0.2878   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -2.1370   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.5116   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.9303   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.2129    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.6995   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    1.9519   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7861    1.2020   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.5860    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 10  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])C(=O)OC([H])([H])C1([H])[H]

> <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_KEY>
YRYOXRMDHALAFL-QMMMGPOBSA-N

> <FORMULA>
C10H15NO4

> <MOLECULAR_WEIGHT>
213.233

> <EXACT_MASS>
213.100107967

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.980454044592864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
0.2846146659999998

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.191218920195336

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.295823459045753

> <JCHEM_PKA_STRONGEST_BASIC>
-3.910325194816417

> <JCHEM_POLAR_SURFACE_AREA>
72.47

> <JCHEM_REFRACTIVITY>
51.98110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    5.1285    1.0749    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -0.0305    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    0.1740   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036   -1.0001   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -1.9057    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.0849   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -0.5939   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.1911    1.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -0.5950   -0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.1310    0.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6157    0.9589   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9384    0.9029    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -0.4170    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -1.1609    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -2.4007    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.6211    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.6538    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    1.7465   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0234    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.0868    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    1.1278   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    0.2878   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -2.1370   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.5116   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.9303   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.2129    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.6995   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    1.9519   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7861    1.2020   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.5860    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.128   1.075   0.316  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.124  -0.031   0.442  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.900   0.174  -0.424  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.004  -1.000  -0.188  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.288  -1.906   0.579  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.704  -1.085  -0.913  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.420  -0.594  -0.064  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.199  -0.191   1.106  0.00  0.00           O+0
HETATM    9  N   UNK     0      -1.717  -0.595  -0.605  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.846  -0.131   0.160  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.616   0.959  -0.540  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.938   0.903   0.193  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.058  -0.417   0.657  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.911  -1.161   0.327  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.798  -2.401   0.202  0.00  0.00           O+0
HETATM   16  H   UNK     0       6.136   0.621   0.185  0.00  0.00           H+0
HETATM   17  H   UNK     0       5.188   1.654   1.260  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.967   1.746  -0.552  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.560  -1.023   0.209  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.780  -0.087   1.487  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.400   1.128  -0.117  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.168   0.288  -1.494  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.474  -2.137  -1.172  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.724  -0.512  -1.861  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.900  -0.930  -1.575  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.543   0.213   1.146  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.826   0.700  -1.608  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.127   1.952  -0.479  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.786   1.202  -0.457  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.861   1.586   1.066  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3   19   20                                             
CONECT    3    2    4   21   22                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   23   24                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11   14   26                                             
CONECT   11   10   12   27   28                                             
CONECT   12   11   13   29   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   10                                                  
CONECT   15   14                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    6                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   12                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

RDKit          3D

30 30  0  0  0  0  0  0  0  0999 V2000
    5.1285    1.0749    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -0.0305    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    0.1740   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0036   -1.0001   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -1.9057    0.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.0849   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -0.5939   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -0.1911    1.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -0.5950   -0.6051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.1310    0.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6157    0.9589   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9384    0.9029    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0583   -0.4170    0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -1.1609    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7976   -2.4007    0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1358    0.6211    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.6538    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670    1.7465   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5604   -1.0234    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800   -0.0868    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    1.1278   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685    0.2878   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -2.1370   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239   -0.5116   -1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002   -0.9303   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.2129    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    0.6995   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1271    1.9519   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7861    1.2020   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    1.5860    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  9 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(S)-3-(3-Ketohexanamido)-2-oxotetrahydrofuran	ChEBI
(S)-3-(3-Ketohexanamido)butyrolactone	ChEBI
(S)-3-(3-Oxohexanamido)-2-oxotetrahydrofuran	ChEBI
(S)-3-(3-Oxohexanamido)butyrolactone	ChEBI
N-(3-Ketocaproyl)-L-homoserine lactone	ChEBI
N-(3-Ketohexanoyl)-L-homoserine lactone	ChEBI
N-(beta-Ketocaproyl)-L-homoserine lactone	ChEBI
N-(b-Ketocaproyl)-L-homoserine lactone	Generator
N-(Β-ketocaproyl)-L-homoserine lactone	Generator
3-oxo-C6-AHL	MeSH
Luciferase autoinducer	MeSH
AI-1 lactone	MeSH
N-(3-Oxohexanoyl)-3-aminodihydro-2(3H)-furanone	MeSH
N-(beta-Ketocaproyl)homoserine lactone	MeSH
Autoinducer 1	MeSH
N-(3-Oxohexanoyl)homoserine lactone	MeSH
N-3-Oxohexanoyl-L-homoserine lactone	MeSH
OHHL-N	MeSH
VAI-1	MeSH

Chemical Formula

C₁₀H₁₅NO₄

Average Mass

213.2330 Da

Monoisotopic Mass

213.10011 Da

IUPAC Name

3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide

Traditional Name

3-oxo-N-[(3S)-2-oxooxolan-3-yl]hexanamide

CAS Registry Number

Not 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 Key

YRYOXRMDHALAFL-QMMMGPOBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Azospirillum lipoferum	LOTUS Database	35616633
Erwinia	NPAtlas	1335238
Erwinia carotovora	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.09	ALOGPS
logP	0.28	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	10.3	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.98 m³·mol⁻¹	ChemAxon
Polarizability	21.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003620

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

599950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

63789

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for Autoinducer I (NP0004766)

MOL for NP0004766 (Autoinducer I)

3D MOL for NP0004766 (Autoinducer I)

3D SDF for NP0004766 (Autoinducer I)

3D-SDF for NP0004766 (Autoinducer I)

PDB for NP0004766 (Autoinducer I)

3D PDB for NP0004766 (Autoinducer I)

SMILES for NP0004766 (Autoinducer I)

INCHI for NP0004766 (Autoinducer I)

Structure for NP0004766 (Autoinducer I)

3D Structure for NP0004766 (Autoinducer I)