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Showing NP-Card for 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid (NP0253149)

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Record Information
Version2.0
Created at2022-09-07 16:55:59 UTC
Updated at2022-09-07 16:55:59 UTC
NP-MRD IDNP0253149
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
DescriptionPenicillic acid, also known as penicillate or acid, penicillic, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Penicillic acid has been shown to inhibit alcohol and lactate dehydrogenases by forming covalent adducts with either cysteine or lysine residues at the enzyme active sites. Penicillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Penicillic acid is a potentially toxic compound. Penicillic acid is a mycotoxin produced by several species of Aspergillus and Penicillium. Penicillic acid is rapidly absorbed and extensively metabolized in the liver. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. Penicillic acid is a human health hazard because it can be found on contaminated crops such as corn. It has antibiotic activity and is cytotoxic, hepatotoxic, and carcinogenic. They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. Detoxification occurs via interactions with glutathione S-transferases and metabolites are excreted mainly in the urine. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). 3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid is found in Aspergillus melleus, Aspergillus sclerotiorum, Penicillium aurantiogriseum and Pseudopenicillium megasporum. Penicillic acid is also mutagenic and can cause DNA single-strand breaks, chromosome aberrations, and inhibition of DNA synthesis.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)


  Mrv0541 02241212462D          

 12 11  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    1.5668   -1.7462    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5522   -0.4786    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460    0.0538    1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395    0.4949    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    1.7307    0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447    0.5882   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203   -0.0704   -1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -1.4055   -1.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841   -1.6222   -2.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0361   -2.5314   -1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9329    2.0535   -0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    2.3422    0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974   -2.3349    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -2.3347   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0300    0.9860    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    0.2020    2.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045   -0.6211    1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    0.6238   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750   -3.1473   -0.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    1.6778    0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923    2.1243    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454    3.4151    0.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 12 20  1  0
 12 21  1  0
 12 22  1  0
  7 18  1  0
 10 19  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  1 13  1  0
  1 14  1  0
M  END
Download

3D SDF for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)


  Mrv0541 02241212462D          

 12 11  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=CC(O)=O)C(=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)

> <INCHI_KEY>
VOUGEZYPVGAPBB-UHFFFAOYSA-N

> <FORMULA>
C8H10O4

> <MOLECULAR_WEIGHT>
170.1626

> <EXACT_MASS>
170.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.212254630389133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.0347243956666672

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2046992558090825

> <JCHEM_PKA_STRONGEST_BASIC>
-4.951998160526113

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
43.8815

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penicillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)

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PDB for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)
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  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.540   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      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)
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SMILES for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)
COC(=CC(O)=O)C(=O)C(C)=C
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INCHI for NP0253149 (3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid)
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)
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View in JSmol
Synonyms
ValueSource
PenicillateGenerator
Acid, penicillicMeSH
Chemical FormulaC8H10O4
Average Mass170.1626 Da
Monoisotopic Mass170.05791 Da
IUPAC Name3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid
Traditional Namepenicillic acid
CAS Registry NumberNot Available
SMILES
COC(=CC(O)=O)C(=O)C(C)=C
InChI Identifier
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)
InChI KeyVOUGEZYPVGAPBB-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
Aspergillus melleusLOTUS Database
Aspergillus sclerotiorumLOTUS Database
Penicillium aurantiogriseumLOTUS Database
Pseudopenicillium megasporumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassMedium-chain keto acids and derivatives  
Direct ParentMedium-chain keto acids and derivatives  
Alternative Parents
Substituents
  • Medium-chain keto acid
    • 

  • Branched fatty acid
    • 

  • Fatty acyl
    • 

  • Alpha-branched alpha,beta-unsaturated-ketone
    • 

  • Unsaturated fatty acid
    • 

  • Acryloyl-group
    • 

  • Enone
    • 

  • Vinylogous ester
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP1.15ALOGPS
logP1.03ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.88 m³·mol⁻¹ChemAxon
Polarizability16.21 ųChemAxon
Number of Rings0ChemAxon
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPenicillic acid  
METLIN IDNot Available
PubChem Compound7025  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]