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Showing NP-Card for 3-Oxoadipate enol-lactone (NP0054985)

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Record Information
Version2.0
Created at2022-04-28 01:10:16 UTC
Updated at2022-04-28 01:10:16 UTC
NP-MRD IDNP0054985
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Oxoadipate enol-lactone
Description 3-Oxoadipate enol-lactone is found in Pseudomonas putida. 3-Oxoadipate enol-lactone was first documented in 1993 (PMID: 7684040).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054985 (3-Oxoadipate enol-lactone)

 
  Mrv1533006041517152D          
 
 10 10  0  0  0  0            999 V2000
    9.3512   -7.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0536   -8.4194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -8.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -7.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8400   -8.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -9.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8004   -7.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5540   -8.9717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3364   -7.5765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7911   -8.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for NP0054985 (3-Oxoadipate enol-lactone)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.0421    1.7590    1.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1150    0.6614    0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887   -0.3449    1.1088 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771    0.4643   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    0.1882   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751   -0.8757   -0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419   -0.7249   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    0.6112    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    1.2548    1.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    1.1199    0.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9641   -1.2512    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.3202   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3880    1.4349   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4021   -1.7315   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -1.4959    0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9175   -0.7494   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  7 16  1  0
M  END
Download

3D SDF for NP0054985 (3-Oxoadipate enol-lactone)

 
  Mrv1533006041517152D          
 
 10 10  0  0  0  0            999 V2000
    9.3512   -7.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0536   -8.4194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -8.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -7.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8400   -8.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -9.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8004   -7.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5540   -8.9717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3364   -7.5765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7911   -8.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O4/c7-5(8)3-4-1-2-6(9)10-4/h1H,2-3H2,(H,7,8)

> <INCHI_KEY>
ZPEHSARSWGDCEX-UHFFFAOYSA-N

> <FORMULA>
C6H6O4

> <MOLECULAR_WEIGHT>
142.11

> <EXACT_MASS>
142.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.561880245494766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(5-oxo-4,5-dihydrofuran-2-yl)acetic acid

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.4079421826666667

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.04968688660124

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7979716129953345

> <JCHEM_PKA_STRONGEST_BASIC>
-7.215706990605494

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
32.2557

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxoadipate enol-lactone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0054985 (3-Oxoadipate enol-lactone)

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PDB for NP0054985 (3-Oxoadipate enol-lactone)
HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      17.456 -14.599   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      18.767 -15.716   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      17.456 -16.679   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.884 -14.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.235 -16.753   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.884 -17.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.161 -14.694   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      21.568 -16.747   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.161 -14.143   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      20.143 -15.884   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    6                                                  
CONECT    6    3    5                                                       
CONECT    7    4    9   10                                                  
CONECT    8    5                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0054985 (3-Oxoadipate enol-lactone)
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SMILES for NP0054985 (3-Oxoadipate enol-lactone)
OC(=O)CC1=CCC(=O)O1
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INCHI for NP0054985 (3-Oxoadipate enol-lactone)
InChI=1S/C6H6O4/c7-5(8)3-4-1-2-6(9)10-4/h1H,2-3H2,(H,7,8)
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View in JSmol
Synonyms
ValueSource
2-oxo-2,3-Dihydrofuran-5-acetateChEBI
3-Oxoadipate enol-lactoneChEBI
4,5-Dihydro-5-oxofuran-2-acetateChEBI
5-oxo-4,5-Dihydrofuran-2-acetateChEBI
2-oxo-2,3-Dihydrofuran-5-acetic acidGenerator
3-Oxoadipic acid enol-lactoneGenerator
4,5-Dihydro-5-oxofuran-2-acetic acidGenerator
5-oxo-4,5-Dihydrofuran-2-acetic acidGenerator
5-oxo-4,5-Dihydro-2-furylacetateGenerator
Chemical FormulaC6H6O4
Average Mass142.1100 Da
Monoisotopic Mass142.02661 Da
IUPAC Name2-(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
Traditional Name3-oxoadipate enol-lactone
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CCC(=O)O1
InChI Identifier
InChI=1S/C6H6O4/c7-5(8)3-4-1-2-6(9)10-4/h1H,2-3H2,(H,7,8)
InChI KeyZPEHSARSWGDCEX-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
Pseudomonas putidaBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassDicarboxylic acids and derivatives  
Direct ParentDicarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
    • 

  • Enol ester
    • 

  • Dihydrofuran
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.24ALOGPS
logP-0.41ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.26 m³·mol⁻¹ChemAxon
Polarizability12.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007489  
Chemspider IDNot Available
KEGG Compound IDC03586  
BioCyc ID3-OXOADIPATE-ENOL-LACTONE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound104  
PDB IDNot Available
ChEBI ID18267  
Good Scents IDNot Available
References
General References
  1. Schlomann M, Ngai KL, Ornston LN, Knackmuss HJ: Dienelactone hydrolase from Pseudomonas cepacia. J Bacteriol. 1993 May;175(10):2994-3001. doi: 10.1128/jb.175.10.2994-3001.1993. [PubMed:7684040  ] 
  2. Eulberg D, Lakner S, Golovleva LA, Schlomann M: Characterization of a protocatechuate catabolic gene cluster from Rhodococcus opacus 1CP: evidence for a merged enzyme with 4-carboxymuconolactone-decarboxylating and 3-oxoadipate enol-lactone-hydrolyzing activity. J Bacteriol. 1998 Mar;180(5):1072-81. doi: 10.1128/JB.180.5.1072-1081.1998. [PubMed:9495744  ]