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Showing NP-Card for Homoserine lactone (NP0084101)

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Record Information
Version2.0
Created at2022-04-29 04:56:25 UTC
Updated at2022-04-29 04:56:25 UTC
NP-MRD IDNP0084101
Secondary Accession NumbersNone
Natural Product Identification
Common NameHomoserine lactone
DescriptionL-3-Aminodihydro-2(3H)-furanone, also known as Hsl or 2-aminobutan-4-olide, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. L-3-Aminodihydro-2(3H)-furanone is a very strong basic compound (based on its pKa). Outside of the human body, L-3-Aminodihydro-2(3H)-furanone has been detected, but not quantified in, common pea and pulses. This could make L-3-aminodihydro-2(3H)-furanone a potential biomarker for the consumption of these foods. Homoserine lactone is found in Paraburkholderia phymatum and Trypanosoma brucei. Homoserine lactone was first documented in 1994 (PMID: 7545940). A butan-4-olide having an amino substituent at the 2-position.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084101 (Homoserine lactone)


  Mrv0541 02241217442D          

  7  7  0  0  0  0            999 V2000
   -0.6780    1.0648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694    0.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503   -0.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2985   -0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    0.4117    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
  2  6  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  2  0  0  0  0
M  END
Download

3D MOL for NP0084101 (Homoserine lactone)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -1.6531   -0.4775   -0.2280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    0.2596    0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5648   -0.5907    0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -0.2676   -0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011    0.7910   -1.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588    1.3819   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4517    2.6000   -0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455   -0.0935   -1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048   -1.3993    0.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    0.6085    1.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0715   -0.2179    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201   -1.6469    0.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740   -1.1276   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    0.1800   -0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  1
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
M  END
Download

3D SDF for NP0084101 (Homoserine lactone)


  Mrv0541 02241217442D          

  7  7  0  0  0  0            999 V2000
   -0.6780    1.0648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694    0.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503   -0.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2985   -0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    0.4117    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
  2  6  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  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO2/c5-3-1-2-7-4(3)6/h3H,1-2,5H2

> <INCHI_KEY>
QJPWUUJVYOJNMH-UHFFFAOYSA-N

> <FORMULA>
C4H7NO2

> <MOLECULAR_WEIGHT>
101.1039

> <EXACT_MASS>
101.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.465128241694444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminooxolan-2-one

> <ALOGPS_LOGP>
-1.39

> <JCHEM_LOGP>
-0.9011904176666667

> <ALOGPS_LOGS>
0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.329657478497863

> <JCHEM_POLAR_SURFACE_AREA>
52.32

> <JCHEM_REFRACTIVITY>
23.4142

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HSLs

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0084101 (Homoserine lactone)

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PDB for NP0084101 (Homoserine lactone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.266   1.988   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.876   0.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.853  -0.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.021  -1.988   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.467  -1.599   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.557  -0.064   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.853   0.769   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0084101 (Homoserine lactone)
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SMILES for NP0084101 (Homoserine lactone)
NC1CCOC1=O
Download
INCHI for NP0084101 (Homoserine lactone)
InChI=1S/C4H7NO2/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
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View in JSmol
Synonyms
ValueSource
2-Aminobutan-4-olideChEBI
alpha-Amino-gamma-butyrolactoneChEBI
HslChEBI
HSLSChEBI
a-Amino-g-butyrolactoneGenerator
Α-amino-γ-butyrolactoneGenerator
Homoserine lactone hydrochloride, (S)-isomerMeSH
Homoserine lactone, (S)-isomerMeSH
Homoserine lactone hydrobromideMeSH
Homoserine lactoneMeSH
Chemical FormulaC4H7NO2
Average Mass101.1039 Da
Monoisotopic Mass101.04768 Da
IUPAC Name3-aminooxolan-2-one
Traditional NameHSLs
CAS Registry NumberNot Available
SMILES
NC1CCOC1=O
InChI Identifier
InChI=1S/C4H7NO2/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
InChI KeyQJPWUUJVYOJNMH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Paraburkholderia phymatum-
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acid esters  
Alternative Parents
Substituents
  • Alpha-amino acid ester
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic nitrogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-0.9ChemAxon
logS0.84ALOGPS
pKa (Strongest Basic)7.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.41 m³·mol⁻¹ChemAxon
Polarizability9.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029387  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000468  
KNApSAcK IDNot Available
Chemspider ID66194  
KEGG Compound IDC02926  
BioCyc IDHOMOSERINE-LACTONE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73509  
PDB IDNot Available
ChEBI ID17289  
Good Scents IDNot Available
References
General References
  1. Huisman GW, Kolter R: Sensing starvation: a homoserine lactone--dependent signaling pathway in Escherichia coli. Science. 1994 Jul 22;265(5171):537-9. doi: 10.1126/science.7545940. [PubMed:7545940  ]