Showing NP-Card for C4-HSL (NP0084568)

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Record Information
Version2.0
Created at2022-04-29 05:16:10 UTC
Updated at2022-04-29 05:16:10 UTC
NP-MRD IDNP0084568
Secondary Accession NumbersNone
Natural Product Identification
Common NameC4-HSL
DescriptionN-butanoyl-homoserine lactone, also known as C4-HSL or BHL-serine, 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-butanoyl-homoserine lactone is considered to be a fatty amide lipid molecule. C4-HSL is found in a Pantoea sp., Pantoea sp. and Zea mays . N-butanoyl-homoserine lactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084568 (C4-HSL)

  Mrv0541 05041405172D          

 13 13  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
    1.9967    3.5893    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
   -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
    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
   -0.1673    1.4888    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
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  6  9  1  6  0  0  0
  9  7  2  0  0  0  0
  7 10  1  4  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
  6 13  1  1  0  0  0
M  END
Download

3D MOL for NP0084568 (C4-HSL)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    3.5525    0.4758    0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5124   -0.3713   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.5712   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3643   -0.2022   -1.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.9652   -2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -0.2112   -1.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057    0.5151    0.0569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8985    0.7220   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5265   -0.1662    1.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4365   -0.9735    1.4519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -0.2376    1.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -0.2134    2.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817    0.2056    0.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601    0.2523    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3590    1.5550    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256   -1.0375    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9392   -0.9412   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9310    1.2649   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    1.1497    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2671   -1.8555   -2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    1.5272    0.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    0.4087   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    1.7540    0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619    0.4079    1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2642   -0.8469    0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 11  7  1  0
  7 21  1  1
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  5 20  1  0
  3 18  1  0
  3 19  1  0
  2 16  1  0
  2 17  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
M  END
Download

3D SDF for NP0084568 (C4-HSL)

  Mrv0541 05041405172D          

 13 13  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
    1.9967    3.5893    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
   -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
    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
   -0.1673    1.4888    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
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  6  9  1  6  0  0  0
  9  7  2  0  0  0  0
  7 10  1  4  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
  6 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0084568

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1

> <INCHI_KEY>
VFFNZZXXTGXBOG-LURJTMIESA-N

> <FORMULA>
C8H13NO3

> <MOLECULAR_WEIGHT>
171.1937

> <EXACT_MASS>
171.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.56669288967514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
0.8823648243333331

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.454490004875519

> <JCHEM_PKA_STRONGEST_BASIC>
1.3481039728207138

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
42.607600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0084568 (C4-HSL)

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PDB for NP0084568 (C4-HSL)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4    8    9   13                                             
CONECT    7    3    9   10                                                  
CONECT    8    6   11   12                                                  
CONECT    9    6    7                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    5    8                                                       
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0084568 (C4-HSL)
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SMILES for NP0084568 (C4-HSL)
[H][C@@]1(CCOC1=O)N=C(O)CCC
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INCHI for NP0084568 (C4-HSL)
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
N-Butyryl-L-homoserine lactoneMeSH
N-Butyrylhomoserine lactoneMeSH
C4-HSLMeSH
N-Butanoyl-L-homoserine lactoneMeSH
C(4)-HSLMeSH
BHL-SerineMeSH
BHL CPDMeSH
PAI-2 CPDMeSH
Chemical FormulaC8H13NO3
Average Mass171.1937 Da
Monoisotopic Mass171.08954 Da
IUPAC NameN-[(3S)-2-oxooxolan-3-yl]butanimidic acid
Traditional NameN-[(3S)-2-oxooxolan-3-yl]butanimidic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CCOC1=O)N=C(O)CCC
InChI Identifier
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1
InChI KeyVFFNZZXXTGXBOG-LURJTMIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
a Pantoea sp.-
Pantoea sp.-
Zea mays L.Plant
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentN-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • Fatty acyl homoserine lactones (C11837  )
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
logP0.76ALOGPS
logP0.88ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.45ChemAxon
pKa (Strongest Basic)1.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.61 m³·mol⁻¹ChemAxon
Polarizability17.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11837  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10130163  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available