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Showing NP-Card for (2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid (NP0218514)

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Record Information
Version2.0
Created at2022-09-05 19:12:21 UTC
Updated at2022-09-05 19:12:21 UTC
NP-MRD IDNP0218514
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid
Description(2E)-3-[(5E)-2-oxo-5-propylidene-2,5-dihydrofuran-3-yl]prop-2-enoic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid is found in Bombardioidea anartia. Based on a literature review very few articles have been published on (2E)-3-[(5E)-2-oxo-5-propylidene-2,5-dihydrofuran-3-yl]prop-2-enoic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)


  Mrv1652309052221122D          

 14 14  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
Download

3D MOL for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    4.0408   -0.2146   -0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0112   -1.0143   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.1075    0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2901    0.2329    1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071   -0.1979    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603    0.3431    0.5394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281    0.0973   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3711    0.6289    0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230    0.3330   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6840    0.8591   -0.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589   -0.4967   -1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    1.1569    1.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    1.8222    2.3358 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7185    1.0856    1.9799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    0.6097   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5984   -0.8684   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128    0.3017   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5789   -1.8423    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027   -1.3804   -0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    0.2991    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878   -0.8652   -0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2747   -0.5626   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3790    1.2814    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6316   -1.5007   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4 14  1  0
 14 12  1  0
 12 13  2  0
 12  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  6  5  2  0
  5  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  7 22  1  0
  8 23  1  0
 11 24  1  0
  5 21  1  0
M  END
Download

3D SDF for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)


  Mrv1652309052221122D          

 14 14  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2790   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C1\OC(=O)C(\C=C\C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-2-3-8-6-7(10(13)14-8)4-5-9(11)12/h3-6H,2H2,1H3,(H,11,12)/b5-4+,8-3+

> <INCHI_KEY>
LNEPPGKBSBTFDF-JPXXCTSLSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.672347789188986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(5E)-2-oxo-5-propylidene-2,5-dihydrofuran-3-yl]prop-2-enoic acid

> <JCHEM_LOGP>
1.5502946143333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.392612642332494

> <JCHEM_PKA_STRONGEST_BASIC>
-7.076275612289362

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
52.60240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(5E)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)

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PDB for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.014  -4.188   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.545  -4.027   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.387  -5.595   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)
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SMILES for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)
CC\C=C1\OC(=O)C(\C=C\C(O)=O)=C1
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INCHI for NP0218514 ((2e)-3-[(5e)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid)
InChI=1S/C10H10O4/c1-2-3-8-6-7(10(13)14-8)4-5-9(11)12/h3-6H,2H2,1H3,(H,11,12)/b5-4+,8-3+
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View in JSmol
Synonyms
ValueSource
(2E)-3-[(5E)-2-oxo-5-Propylidene-2,5-dihydrofuran-3-yl]prop-2-enoateGenerator
Chemical FormulaC10H10O4
Average Mass194.1860 Da
Monoisotopic Mass194.05791 Da
IUPAC Name(2E)-3-[(5E)-2-oxo-5-propylidene-2,5-dihydrofuran-3-yl]prop-2-enoic acid
Traditional Name(2E)-3-[(5E)-2-oxo-5-propylidenefuran-3-yl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C1\OC(=O)C(\C=C\C(O)=O)=C1
InChI Identifier
InChI=1S/C10H10O4/c1-2-3-8-6-7(10(13)14-8)4-5-9(11)12/h3-6H,2H2,1H3,(H,11,12)/b5-4+,8-3+
InChI KeyLNEPPGKBSBTFDF-JPXXCTSLSA-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
Bombardioidea anartiaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Enol ester
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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
logP1.55ChemAxon
pKa (Strongest Acidic)4.39ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.6 m³·mol⁻¹ChemAxon
Polarizability19.67 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 IDC00045692  
Chemspider ID9920217  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11745513  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]