MiMeDB: Showing metabocard for N-(3-oxododecanoyl)-L-homoserine lactone (MMDBc0032883)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:06 UTC

Update Date

2022-08-31 21:45:03 UTC

Metabolite ID

MMDBc0032883

Metabolite Identification

Common Name

N-(3-oxododecanoyl)-L-homoserine lactone

Description

An N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent.

Structure

MOL SDF PDB SMILES InChI

OHN
  Mrv0541 02241214012D          

 22 22  0  0  0  0            999 V2000
   -6.5581   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8437   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1292   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4147   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7002   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9858   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1279   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1279   -3.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -2.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -3.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0155   -2.5880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -3.0005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4837   -2.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357   -3.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162   -3.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -4.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232   -3.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7606   -2.4173    0.0000 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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 22  1  6  0  0  0
 17 18  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032883

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1

> <INCHI_KEY>
PHSRRHGYXQCRPU-AWEZNQCLSA-N

> <FORMULA>
C16H27NO4

> <MOLECULAR_WEIGHT>
297.3899

> <EXACT_MASS>
297.194008357

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.12098628302368

> <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]dodecanamide

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.952026656

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.298764163736983

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.310716116729928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.910333054413034

> <JCHEM_POLAR_SURFACE_AREA>
72.47

> <JCHEM_REFRACTIVITY>
79.58709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-C12-HSL

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: OHN                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -12.242  -4.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.908  -5.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.575  -4.831   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.241  -5.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.907  -4.831   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.573  -5.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.240  -4.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.906  -5.601   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.572  -4.831   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.239  -5.601   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.239  -7.141   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.095  -4.831   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.429  -5.601   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.429  -7.141   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       3.762  -4.831   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.096  -5.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.503  -4.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.533  -6.119   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.257  -7.133   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.112  -8.163   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.763  -7.453   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       5.153  -4.512   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19   22                                             
CONECT   17   16   18                                                       
CONECT   18   17   21                                                       
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   18   19                                                       
CONECT   22   16                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

Synonyms

Value	Source
3-oxo-C12-AHL	ChEBI
3-oxo-C12-HSL	ChEBI
N-(3-Ketododecanoyl)-L-homoserine lactone	ChEBI
3-oxo-C8-HSL	MeSH
N-(3-Oxododecanoyl)-L-homoserine lactone	MeSH
N-(3-Oxododecanoyl)homoserine lactone	MeSH
N-3-Oxododecanoyl-L-homoserine lactone	MeSH
3O-C12-HSL	MeSH
N-(3-Oxododecanoyl)-homoserine lactone	MeSH
N3-ODDHL	MeSH

Molecular Formula

C₁₆H₂₇NO₄

Average Mass

297.3899

Monoisotopic Mass

297.194008357

IUPAC Name

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

Traditional Name

3-oxo-C12-HSL

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CCOC1=O)NC(=O)CC(=O)CCCCCCCCC

InChI Identifier

InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1

InChI Key

PHSRRHGYXQCRPU-AWEZNQCLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Acyl-homoserine lactone
Acyl-l-homoserine lactone
Fatty amide
Gamma butyrolactone
Fatty acyl
1,3-dicarbonyl compound
N-acyl-amine
Tetrahydrofuran
Carboxamide group
Carboxylic acid ester
Ketone
Secondary carboxylic acid amide
Lactone
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl-L-homoserine lactone (CHEBI:44534 )
N-(3-oxododecanoyl)homoserine lactone (CHEBI:44534 )
Fatty acyl homoserine lactones (LMFA08030001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.95	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.31	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	11	ChemAxon
Refractivity	79.59 m³·mol⁻¹	ChemAxon
Polarizability	34.12 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5910000000-1e3b0259204d0eae8a08	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-1970000000-5f7584e38fa90e054b6d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-4900000000-e0eb86f4821529f43364	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfu-9400000000-6716e51a02bc30a481eb	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0390000000-058623277c343f8c6b0d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f92-3960000000-3a528e92ed2576714bdd	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02mm-9300000000-6810d4aad2020f6dcf6b	2017-07-26	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB08324

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3246941

PDB ID

Not Available

ChEBI ID

44534

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Huang W, Brewer LK, Jones JW, Nguyen AT, Marcu A, Wishart DS, Oglesby-Sherrouse AG, Kane MA, Wilks A: PAMDB: a comprehensive Pseudomonas aeruginosa metabolome database. Nucleic Acids Res. 2018 Jan 4;46(D1):D575-D580. doi: 10.1093/nar/gkx1061. [PubMed:29106626 ]

Showing metabocard for N-(3-oxododecanoyl)-L-homoserine lactone (MMDBc0032883)

MOL for #<Metabolite:0x00007f46d84dc9b8>

3D MOL for #<Metabolite:0x00007f46d84dc9b8>

3D SDF for #<Metabolite:0x00007f46d84dc9b8>

3D-SDF for #<Metabolite:0x00007f46d84dc9b8>

PDB for #<Metabolite:0x00007f46d84dc9b8>

3D PDB for #<Metabolite:0x00007f46d84dc9b8>

SMILES for #<Metabolite:0x00007f46d84dc9b8>

INCHI for #<Metabolite:0x00007f46d84dc9b8>

Structure for #<Metabolite:0x00007f46d84dc9b8>

3D Structure for #<Metabolite:0x00007f46d84dc9b8>