MiMeDB: Showing metabocard for N-isovaleryl-L-homoserine lactone (MMDBc0056151)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:18:10 UTC

Update Date

2025-10-07 16:09:35 UTC

Metabolite ID

MMDBc0056151

Metabolite Identification

Common Name

N-isovaleryl-L-homoserine lactone

Description

N-isovaleryl-L-homoserine lactone is a member of the class of homoserine lactones, which are signaling molecules involved in quorum sensing in various bacteria. There is limited literature available on this specific metabolite, indicating that further research may be necessary to fully understand its biological significance and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222182D          

 14 14  0  0  1  0            999 V2000
    1.9967    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
  7 10  1  6  0  0  0
 10  8  2  0  0  0  0
  8 11  1  4  0  0  0
 12  9  2  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
  7 14  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0056151

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO3/c1-6(2)5-8(11)10-7-3-4-13-9(7)12/h6-7H,3-5H2,1-2H3,(H,10,11)/t7-/m0/s1

> <INCHI_KEY>
DUHWGLQNCKHNBY-ZETCQYMHSA-N

> <FORMULA>
C9H15NO3

> <MOLECULAR_WEIGHT>
185.223

> <EXACT_MASS>
185.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.259453029100207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.1693839206666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.8321124812513006

> <JCHEM_PKA_STRONGEST_BASIC>
1.4324074909423083

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
47.15620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       3.727   8.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.727   6.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.060   3.620   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.432   2.779   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    4    7                                                       
CONECT    4    3   13                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    9   10   14                                             
CONECT    8    5   10   11                                                  
CONECT    9    7   12   13                                                  
CONECT   10    7    8                                                       
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    4    9                                                       
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
N-Isopentanoyl-L-homoserine lactone	ChEBI

Molecular Formula

C₉H₁₅NO₃

Average Mass

185.223

Monoisotopic Mass

185.105193347

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H15NO3/c1-6(2)5-8(11)10-7-3-4-13-9(7)12/h6-7H,3-5H2,1-2H3,(H,10,11)/t7-/m0/s1

InChI Key

DUHWGLQNCKHNBY-ZETCQYMHSA-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
Tetrahydrofuran
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl-L-homoserine lactone (CHEBI:74958 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.17	ChemAxon
pKa (Strongest Acidic)	5.83	ChemAxon
pKa (Strongest Basic)	1.43	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	3	ChemAxon
Refractivity	47.16 m³·mol⁻¹	ChemAxon
Polarizability	19.26 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_1_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
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	131.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	44.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	344.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	411.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	362.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	283.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1420.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	63.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	454.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	291.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	178.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	168.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	114.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	74.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	344.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	77.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	277.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1067.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	765.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-isovaleryl-L-homoserine lactone_TMS_1	CC(C)CC(=N[C@H]1CCOC1=O)O[Si](C)(C)C	standard non polar	2025-10-24	2021.07
Gas Chromatography	N-isovaleryl-L-homoserine lactone_TMS_1	CC(C)CC(=N[C@H]1CCOC1=O)O[Si](C)(C)C	standard polar	2025-10-24	1995.73

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	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

29368455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71627311

PDB ID

Not Available

ChEBI ID

74958

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-isovaleryl-L-homoserine lactone (MMDBc0056151)

MOL for #<Metabolite:0x00007f9af03d7dd0>

3D MOL for #<Metabolite:0x00007f9af03d7dd0>

3D SDF for #<Metabolite:0x00007f9af03d7dd0>

3D-SDF for #<Metabolite:0x00007f9af03d7dd0>

PDB for #<Metabolite:0x00007f9af03d7dd0>

3D PDB for #<Metabolite:0x00007f9af03d7dd0>

SMILES for #<Metabolite:0x00007f9af03d7dd0>

INCHI for #<Metabolite:0x00007f9af03d7dd0>

Structure for #<Metabolite:0x00007f9af03d7dd0>

3D Structure for #<Metabolite:0x00007f9af03d7dd0>