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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:33:37 UTC

Update Date

2022-09-22 18:34:49 UTC

HMDB ID

HMDB0341343

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-3-Hydroxyoctanoyl-L-homoserine lactone

Description

853799-77-6 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. 853799-77-6 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191516092D          

 17 17  0  0  0  0            999 V2000
    2.7964   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9398   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -5.1455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -5.1455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.9080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -4.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1198   -5.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997   -5.6930    0.0000 O   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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341343

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)

> <INCHI_KEY>
XCZVBYOXRSFQBH-UHFFFAOYSA-N

> <FORMULA>
C12H21NO4

> <MOLECULAR_WEIGHT>
243.303

> <EXACT_MASS>
243.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.476618902797004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-N-(2-oxooxolan-3-yl)octanamide

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.6102242903333328

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.231191761898927

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.516465201377311

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8909851133164408

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
62.00540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-N-(2-oxooxolan-3-yl)octanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.220  -7.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.554  -8.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.887  -7.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.221  -8.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.555  -7.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.888  -8.065   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.888  -9.605   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.222  -7.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.556  -8.065   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.556  -9.605   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      15.889  -7.295   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      17.223  -8.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.630  -7.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.660  -8.583   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      18.890  -9.917   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.384  -9.597   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.239 -10.627   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-N-(2-oxooxolan-3-yl)octanimidate	Generator

Chemical Formula

C₁₂H₂₁NO₄

Average Molecular Weight

243.303

Monoisotopic Molecular Weight

243.14705816

IUPAC Name

3-hydroxy-N-(2-oxooxolan-3-yl)octanamide

Traditional Name

3-hydroxy-N-(2-oxooxolan-3-yl)octanamide

CAS Registry Number

Not Available

SMILES

CCCCCC(O)CC(=O)NC1CCOC1=O

InChI Identifier

InChI=1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)

InChI Key

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.61	ALOGPS
logP	0.61	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	62.01 m³·mol⁻¹	ChemAxon
Polarizability	26.48 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

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

11586792

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for N-3-Hydroxyoctanoyl-L-homoserine lactone (HMDB0341343)

MOL for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

3D MOL for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

3D SDF for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

3D-SDF for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

PDB for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

3D PDB for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

SMILES for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

INCHI for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

Structure for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

3D Structure for HMDB0341343 (N-3-Hydroxyoctanoyl-L-homoserine lactone)

Predicted Kovats Retention Indices