MiMeDB: Showing metabocard for (S)-N-tetradecanoyl-HSL (MMDBc0006457)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:39:25 UTC

Update Date

2022-08-31 06:25:25 UTC

Metabolite ID

MMDBc0006457

Metabolite Identification

Common Name

(S)-N-tetradecanoyl-HSL

Description

N-tetradecanoyl-L-Homoserine Lactone 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. Thus, N-tetradecanoyl-L-homoserine lactone is considered to be a fatty amide. Based on a literature review a small amount of articles have been published on N-tetradecanoyl-L-Homoserine Lactone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101392D          

 23 23  0  0  1  0            999 V2000
   -5.5836    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7257    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2756    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901    9.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8871    9.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392    9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    9.5548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7045    9.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2197   10.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    9.1423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   10.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066   10.9274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0267   10.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4416   10.0042    0.0000 H   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
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 18 16  1  0  0  0  0
 16 19  1  6  0  0  0
 19 17  2  0  0  0  0
 17 20  1  4  0  0  0
 21 18  2  0  0  0  0
 22 15  1  0  0  0  0
 22 18  1  0  0  0  0
 16 23  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006457

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CCOC1=O)N=C(O)CCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1

> <INCHI_KEY>
ZQAYHOXXVBVXPZ-INIZCTEOSA-N

> <FORMULA>
C18H33NO3

> <MOLECULAR_WEIGHT>
311.466

> <EXACT_MASS>
311.246043927

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.37378887053738

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(3S)-2-oxooxolan-3-yl]tetradecanimidic acid

> <ALOGPS_LOGP>
5.90

> <JCHEM_LOGP>
5.328051474333334

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.956019385637912

> <JCHEM_PKA_STRONGEST_BASIC>
1.5494394655223853

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
88.61759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.16e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3S)-2-oxooxolan-3-yl]tetradecanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -10.423  17.066   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.089  17.836   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.755  17.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.422  17.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.088  17.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.754  17.836   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.421  17.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.087  17.836   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.247  17.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.580  17.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.914  17.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.248  17.836   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.581  17.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.989  17.209   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.020  18.354   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.582  17.836   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.915  17.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.743  19.367   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.249  17.066   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       6.915  19.376   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.599  20.398   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.250  19.687   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       8.291  18.674   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                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   17                                                       
CONECT   14   15   16                                                       
CONECT   15   14   22                                                       
CONECT   16   14   18   19   23                                             
CONECT   17   13   19   20                                                  
CONECT   18   16   21   22                                                  
CONECT   19   16   17                                                       
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   15   18                                                       
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₃₃NO₃

Average Mass

311.466

Monoisotopic Mass

311.246043927

IUPAC Name

N-[(3S)-2-oxooxolan-3-yl]tetradecanimidic acid

Traditional Name

N-[(3S)-2-oxooxolan-3-yl]tetradecanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CCOC1=O)N=C(O)CCCCCCCCCCCCC

InChI Identifier

InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1

InChI Key

ZQAYHOXXVBVXPZ-INIZCTEOSA-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
N-acyl-amine
Fatty acyl
Oxolane
Secondary carboxylic acid amide
Lactone
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00082 g/L	ALOGPS
logP	5.9	ALOGPS
logP	5.33	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.96	ChemAxon
pKa (Strongest Basic)	1.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	88.62 m³·mol⁻¹	ChemAxon
Polarizability	38.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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	2	Human ; Human feces	Metabolic reconstruction

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

21467810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

58122267

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for (S)-N-tetradecanoyl-HSL (MMDBc0006457)

MOL for #<Metabolite:0x00007fece800d688>

3D MOL for #<Metabolite:0x00007fece800d688>

3D SDF for #<Metabolite:0x00007fece800d688>

3D-SDF for #<Metabolite:0x00007fece800d688>

PDB for #<Metabolite:0x00007fece800d688>

3D PDB for #<Metabolite:0x00007fece800d688>

SMILES for #<Metabolite:0x00007fece800d688>

INCHI for #<Metabolite:0x00007fece800d688>

Structure for #<Metabolite:0x00007fece800d688>

3D Structure for #<Metabolite:0x00007fece800d688>