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Showing NP-Card for 5-oxohexanoic acid (NP0153569)

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Record Information
Version2.0
Created at2022-09-02 10:15:08 UTC
Updated at2022-09-02 10:15:08 UTC
NP-MRD IDNP0153569
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-oxohexanoic acid
Description4-Acetylbutyrate, also known as 5-oxohexanoate or 5-ketocaproic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 4-Acetylbutyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-oxohexanoic acid is found in Acaciella angustissima. 5-oxohexanoic acid was first documented in 1986 (PMID: 3715925). A medium-chain fatty acid comprising hexanoic acid carrying a 5-oxo group (PMID: 2505723).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0153569 (5-oxohexanoic acid)


  Mrv1652305052017402D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
M  END
Download

3D MOL for NP0153569 (5-oxohexanoic acid)

     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -3.1095    0.0734    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6408    0.2109   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693    1.1470   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.8304    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -0.6184    0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982    0.6295    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    0.8608    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1615    1.8880    0.9351 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4552    0.0172   -0.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5147    1.0813    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -0.5410   -0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2520   -0.5214    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -0.8863    1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0581   -1.8575   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -1.5014    0.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   -0.5982   -1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9913    0.5422    1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6772    1.5051    0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0976   -0.6008    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0153569 (5-oxohexanoic acid)


  Mrv1652305052017402D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3,(H,8,9)

> <INCHI_KEY>
MGTZCLMLSSAXLD-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.22466494068615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-oxohexanoic acid

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
0.37571122033333354

> <ALOGPS_LOGS>
-0.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.576393557288576

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4754830117379925

> <JCHEM_PKA_STRONGEST_BASIC>
-7.271189224356705

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
31.6891

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0153569 (5-oxohexanoic acid)

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PDB for NP0153569 (5-oxohexanoic acid)
HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    4    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0153569 (5-oxohexanoic acid)
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SMILES for NP0153569 (5-oxohexanoic acid)
CC(=O)CCCC(O)=O
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INCHI for NP0153569 (5-oxohexanoic acid)
InChI=1S/C6H10O3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3,(H,8,9)
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Synonyms
ValueSource
4-Acetyl-butanoic acidChEBI
4-Acetyl-butyric acidChEBI
4-Acetylbutyric acidChEBI
5-Keto-N-caproic acidChEBI
5-Ketocaproic acidChEBI
5-Ketohexanoic acidChEBI
5-Oxocaproic acidChEBI
5-OxohexanoateChEBI
delta-Ketocaproic acidChEBI
delta-Oxocaproic acidChEBI
gamma-Acetylbutyric acidChEBI
4-Acetyl-butanoateGenerator
4-Acetyl-butyrateGenerator
5-Keto-N-caproateGenerator
5-KetocaproateGenerator
5-KetohexanoateGenerator
5-OxocaproateGenerator
5-Oxohexanoic acidGenerator
delta-KetocaproateGenerator
Δ-ketocaproateGenerator
Δ-ketocaproic acidGenerator
delta-OxocaproateGenerator
Δ-oxocaproateGenerator
Δ-oxocaproic acidGenerator
g-AcetylbutyrateGenerator
g-Acetylbutyric acidGenerator
gamma-AcetylbutyrateGenerator
Γ-acetylbutyrateGenerator
Γ-acetylbutyric acidGenerator
4-AcetylbutyrateGenerator
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
IUPAC Name5-oxohexanoic acid
Traditional Name5-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
CC(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-5(7)3-2-4-6(8)9/h2-4H2,1H3,(H,8,9)
InChI KeyMGTZCLMLSSAXLD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acaciella angustissimaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentMedium-chain fatty acids  
Alternative Parents
Substituents
  • Medium-chain fatty acid
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP0.05ALOGPS
logP0.38ChemAxon
logS-0.41ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.69 m³·mol⁻¹ChemAxon
Polarizability13.22 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061881  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02129  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18407  
PDB IDNot Available
ChEBI ID15888  
Good Scents IDNot Available
References
General References
  1. Dangel W, Tschech A, Fuchs G: Enzyme reactions involved in anaerobic cyclohexanol metabolism by a denitrifying Pseudomonas species. Arch Microbiol. 1989;152(3):271-9. doi: 10.1007/BF00409663. [PubMed:2505723  ] 
  2. Olson CT, Yu KO, Hobson DW, Serve MP: The metabolism of n-octane in Fischer 344 rats. Toxicol Lett. 1986 May;31(2):147-50. doi: 10.1016/0378-4274(86)90008-1. [PubMed:3715925  ] 
  3. LOTUS database [Link]