MiMeDB: Showing metabocard for 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (MMDBc0032865)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:03:37 UTC

Update Date

2022-08-31 21:44:41 UTC

Metabolite ID

MMDBc0032865

Metabolite Identification

Common Name

3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide

Description

3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (3-oxo-C12-HSL) is a member N-acyl-homoserine family of small diffusible quorum sensing molecules. N-acyl-homoserine lactones (AHLs) are quorum sensing molecules that control gene expression that is dependen

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311182123032D          

 21 21  0  0  0  0            999 V2000
   -5.0024    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2879    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    7.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    8.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2857    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720    9.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713    7.8369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    9.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    9.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7589    9.6220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    9.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  4  0  0  0
 17 15  2  0  0  0  0
 18 13  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032865

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCC(=O)CC(O)=NC1CCOC1=O

> <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)

> <INCHI_KEY>
PHSRRHGYXQCRPU-UHFFFAOYSA-N

> <FORMULA>
C16H27NO4

> <MOLECULAR_WEIGHT>
297.395

> <EXACT_MASS>
297.194008353

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.08432102630553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-oxo-N-(2-oxooxolan-3-yl)dodecanimidic acid

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.771630783

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.923980670873533

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.751730914071805

> <JCHEM_PKA_STRONGEST_BASIC>
1.107304539534923

> <JCHEM_POLAR_SURFACE_AREA>
75.96

> <JCHEM_REFRACTIVITY>
80.10879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
PA autoinducer

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-21         0                                  
HETATM    1  C   UNK     0      -9.338  14.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.004  15.399   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.670  14.629   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.337  15.399   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.003  14.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.669  15.399   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.336  14.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.002  15.399   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.332  14.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.407  14.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.437  15.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.999  14.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.665  15.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.000  15.399   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.333  15.399   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.161  16.931   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.666  14.629   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.665  16.939   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.333  16.939   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.017  17.961   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.667  17.251   0.000  0.00  0.00           O+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   13                                                       
CONECT   10   11   14                                                       
CONECT   11   10   21                                                       
CONECT   12   13   15                                                       
CONECT   13    9   12   18                                                  
CONECT   14   10   16   17                                                  
CONECT   15   12   17   19                                                  
CONECT   16   14   20   21                                                  
CONECT   17   14   15                                                       
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

Synonyms

Value	Source
3-oxo-C12-AHL	ChEBI
3-oxo-C12-HSL	ChEBI
3-oxo-N-(Tetrahydro-2-oxo-3-furanyl)dodecanamide	ChEBI
N-(3-Ketododecanoyl)homoserine lactone	ChEBI
Pseudomonas aeruginosa autoinducer	ChEBI
3-oxo-C8-HSL	MeSH
3O-C12 Autoinducer	MeSH
3O-C12-HSL	MeSH
N-(3-Oxodecanoyl)homoserine lactone	MeSH
N-(3-Oxododecanoyl)-L-homoserine lactone	MeSH
N-(3-Oxododecanoyl)-homoserine lactone	MeSH
N-(3-Oxododecanoyl)homoserine lactone	MeSH
N-3-Oxodecanoyl homoserine lactone	MeSH
N-3-Oxododecanoyl-L-homoserine lactone	MeSH
N3-ODDHL	MeSH

Molecular Formula

C₁₆H₂₇NO₄

Average Mass

297.395

Monoisotopic Mass

297.194008353

IUPAC Name

3-oxo-N-(2-oxooxolan-3-yl)dodecanimidic acid

Traditional Name

PA autoinducer

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(=O)CC(O)=NC1CCOC1=O

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)

InChI Key

PHSRRHGYXQCRPU-UHFFFAOYSA-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
Beta-hydroxy ketone
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl homoserine lactone (CHEBI:29639 )
Fatty acyl homoserine lactones (C11840 )
an acyl-homoserine lactone (CPD-10783 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.77	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	1.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.96 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	80.11 m³·mol⁻¹	ChemAxon
Polarizability	34.08 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 (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113405

KEGG Compound ID

C11840

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127864

PDB ID

Not Available

ChEBI ID

29639

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 3-Oxo-N-(2-oxotetrahydro-3-furanyl)dodecanamide (MMDBc0032865)

MOL for #<Metabolite:0x00005634bf7b4a90>

3D MOL for #<Metabolite:0x00005634bf7b4a90>

3D SDF for #<Metabolite:0x00005634bf7b4a90>

3D-SDF for #<Metabolite:0x00005634bf7b4a90>

PDB for #<Metabolite:0x00005634bf7b4a90>

3D PDB for #<Metabolite:0x00005634bf7b4a90>

SMILES for #<Metabolite:0x00005634bf7b4a90>

INCHI for #<Metabolite:0x00005634bf7b4a90>

Structure for #<Metabolite:0x00005634bf7b4a90>

3D Structure for #<Metabolite:0x00005634bf7b4a90>