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Showing NP-Card for (2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid (NP0202205)

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Record Information
Version2.0
Created at2022-09-04 21:23:00 UTC
Updated at2022-09-04 21:23:00 UTC
NP-MRD IDNP0202205
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid
DescriptionGibepyrone D belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. (2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid was first documented in 2011 (PMID: 21497643). Based on a literature review a small amount of articles have been published on Gibepyrone D (PMID: 29173624) (PMID: 27990770).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)


  Mrv1652309042223232D          

 14 14  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
Download

3D MOL for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -1.9138   -0.7669   -1.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127    0.2062   -0.9372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6146    1.4591   -0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.8786   -1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087    1.1445   -2.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083    3.2452   -1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -0.1267   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.4071   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5044   -1.7208    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -0.6873    1.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2183   -1.0036    2.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343    0.5831    1.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688    1.5227    2.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    0.8236    0.6391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -1.7671   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -0.4252   -2.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847   -0.8409   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041    2.2194   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754    3.9390   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -2.2436   -0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9044   -2.7206    0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0477   -2.0043    2.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3869   -0.2192    3.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -1.0881    1.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 11 22  1  0
 11 23  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)


  Mrv1652309042223232D          

 14 14  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/C(O)=O)C1=CC=C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-6-3-4-8(14-10(6)13)7(2)5-9(11)12/h3-5H,1-2H3,(H,11,12)/b7-5+

> <INCHI_KEY>
MQNNRPUVAMHCCO-FNORWQNLSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.1078096709077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3-methyl-2-oxo-2H-pyran-6-yl)but-2-enoic acid

> <JCHEM_LOGP>
1.387587221

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.374364528260044

> <JCHEM_PKA_STRONGEST_BASIC>
-6.988187306820555

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
52.28340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)

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PDB for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)
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SMILES for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)
C\C(=C/C(O)=O)C1=CC=C(C)C(=O)O1
Download
INCHI for NP0202205 ((2e)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid)
InChI=1S/C10H10O4/c1-6-3-4-8(14-10(6)13)7(2)5-9(11)12/h3-5H,1-2H3,(H,11,12)/b7-5+
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H10O4
Average Mass194.1860 Da
Monoisotopic Mass194.05791 Da
IUPAC Name(2E)-3-(3-methyl-2-oxo-2H-pyran-6-yl)but-2-enoic acid
Traditional Name(2E)-3-(5-methyl-6-oxopyran-2-yl)but-2-enoic acid
CAS Registry NumberNot Available
SMILES
C\C(=C/C(O)=O)C1=CC=C(C)C(=O)O1
InChI Identifier
InChI=1S/C10H10O4/c1-6-3-4-8(14-10(6)13)7(2)5-9(11)12/h3-5H,1-2H3,(H,11,12)/b7-5+
InChI KeyMQNNRPUVAMHCCO-FNORWQNLSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP1.39ChemAxon
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.28 m³·mol⁻¹ChemAxon
Polarizability19.11 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 ID16737943  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20056005  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang QX, Li SF, Zhao F, Dai HQ, Bao L, Ding R, Gao H, Zhang LX, Wen HA, Liu HW: Chemical constituents from endophytic fungus Fusarium oxysporum. Fitoterapia. 2011 Jul;82(5):777-81. doi: 10.1016/j.fitote.2011.04.002. Epub 2011  Apr 9. [PubMed:21497643  ] 
  2. Beccari G, Colasante V, Tini F, Senatore MT, Prodi A, Sulyok M, Covarelli L: Causal agents of Fusarium head blight of durum wheat (Triticum durum Desf.) in central Italy and their in vitro biosynthesis of secondary metabolites. Food Microbiol. 2018 Apr;70:17-27. doi: 10.1016/j.fm.2017.08.016. Epub 2017 Aug 30. [PubMed:29173624  ] 
  3. Bogner CW, Kamdem RS, Sichtermann G, Matthaus C, Holscher D, Popp J, Proksch P, Grundler FM, Schouten A: Bioactive secondary metabolites with multiple activities from a fungal endophyte. Microb Biotechnol. 2017 Jan;10(1):175-188. doi: 10.1111/1751-7915.12467. Epub  2016 Dec 19. [PubMed:27990770  ] 
  4. LOTUS database [Link]