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Showing NP-Card for 6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one (NP0141540)

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Record Information
Version2.0
Created at2022-09-01 19:53:07 UTC
Updated at2022-09-01 19:53:07 UTC
NP-MRD IDNP0141540
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one
DescriptionGibepyrone A 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. 6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one was first documented in 2016 (PMID: 27856636). Based on a literature review a small amount of articles have been published on gibepyrone A (PMID: 31344458) (PMID: 30200525).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)


  Mrv1652309012221532D          

 12 12  0  0  0  0            999 V2000
    1.4289    3.3000    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
Download

3D MOL for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.6979   -0.9515   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -0.9375   -0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5071    0.1028   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2068    1.3951    0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567    0.0945   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867   -1.0297   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0496   -1.0197   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633    0.1701    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    0.1969    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8848    1.2895    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    2.3807    0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5990    1.2183    0.2713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9956   -1.6056   -1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1151    0.0508   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1345   -1.4033    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437   -1.8914   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    1.2528    0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922    2.0240    0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3278    1.8820   -0.8985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2122   -1.9566   -0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392   -1.9351   -0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -0.6505    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.1480   -0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4066    1.1753    0.7724 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12  5  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
M  END
Download

3D SDF for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)


  Mrv1652309012221532D          

 12 12  0  0  0  0            999 V2000
    1.4289    3.3000    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141540

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-4-7(2)9-6-5-8(3)10(11)12-9/h4-6H,1-3H3/b7-4+

> <INCHI_KEY>
FEEGMVBAILJAQO-QPJJXVBHSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.204

> <EXACT_MASS>
164.083729626

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.27687213358395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2E)-but-2-en-2-yl]-3-methyl-2H-pyran-2-one

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.348083839666667

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.988051357977242

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
50.641300000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2E)-but-2-en-2-yl]-3-methylpyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)

Download
PDB for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)
HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)
Download
SMILES for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)
C\C=C(/C)C1=CC=C(C)C(=O)O1
Download
INCHI for NP0141540 (6-[(2e)-but-2-en-2-yl]-3-methylpyran-2-one)
InChI=1S/C10H12O2/c1-4-7(2)9-6-5-8(3)10(11)12-9/h4-6H,1-3H3/b7-4+
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View in JSmol
Synonyms
ValueSource
6-[(2E)-2-Buten-2-yl]-3-methyl-2H-pyran-2-oneChEBI
Chemical FormulaC10H12O2
Average Mass164.2040 Da
Monoisotopic Mass164.08373 Da
IUPAC Name6-[(2E)-but-2-en-2-yl]-3-methyl-2H-pyran-2-one
Traditional Name6-[(2E)-but-2-en-2-yl]-3-methylpyran-2-one
CAS Registry NumberNot Available
SMILES
C\C=C(/C)C1=CC=C(C)C(=O)O1
InChI Identifier
InChI=1S/C10H12O2/c1-4-7(2)9-6-5-8(3)10(11)12-9/h4-6H,1-3H3/b7-4+
InChI KeyFEEGMVBAILJAQO-QPJJXVBHSA-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
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP3.24ALOGPS
logP2.35ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.64 m³·mol⁻¹ChemAxon
Polarizability18.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8279005  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10103478  
PDB IDNot Available
ChEBI ID156363  
Good Scents IDNot Available
References
General References
  1. Adpressa DA, Connolly LR, Konkel ZM, Neuhaus GF, Chang XL, Pierce BR, Smith KM, Freitag M, Loesgen S: A metabolomics-guided approach to discover Fusarium graminearum metabolites after removal of a repressive histone modification. Fungal Genet Biol. 2019 Nov;132:103256. doi: 10.1016/j.fgb.2019.103256. Epub 2019 Jul 22. [PubMed:31344458  ] 
  2. Westphal KR, Muurmann AT, Paulsen IE, Norgaard KTH, Overgaard ML, Dall SM, Aalborg T, Wimmer R, Sorensen JL, Sondergaard TE: Who Needs Neighbors? PKS8 Is a Stand-Alone Gene in Fusarium graminearum Responsible for Production of Gibepyrones and Prolipyrone B. Molecules. 2018 Sep 2;23(9). pii: molecules23092232. doi: 10.3390/molecules23092232. [PubMed:30200525  ] 
  3. Janevska S, Arndt B, Niehaus EM, Burkhardt I, Rosler SM, Brock NL, Humpf HU, Dickschat JS, Tudzynski B: Gibepyrone Biosynthesis in the Rice Pathogen Fusarium fujikuroi Is Facilitated by a Small Polyketide Synthase Gene Cluster. J Biol Chem. 2016 Dec 30;291(53):27403-27420. doi: 10.1074/jbc.M116.753053. Epub  2016 Nov 17. [PubMed:27856636  ] 
  4. LOTUS database [Link]