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Showing NP-Card for 3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid (NP0243494)

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Record Information
Version2.0
Created at2022-09-07 04:03:25 UTC
Updated at2022-09-07 04:03:26 UTC
NP-MRD IDNP0243494
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid
Description3-[4-Oxo-5-(propan-2-ylidene)-2-propyl-4,5-dihydrofuran-3-yl]prop-2-enoic acid belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. 3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid is found in Lactobacillus helveticus. Based on a literature review very few articles have been published on 3-[4-oxo-5-(propan-2-ylidene)-2-propyl-4,5-dihydrofuran-3-yl]prop-2-enoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)


  Mrv1652309072206032D          

 17 17  0  0  0  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    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
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0306    0.0352    0.0000 O   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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 17  1  0  0  0  0
M  END
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3D MOL for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)

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3D SDF for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)

  Mrv1652309072206032D          

 17 17  0  0  0  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    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
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0306    0.0352    0.0000 O   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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=C(C=CC(O)=O)C(=O)C(O1)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O4/c1-4-5-10-9(6-7-11(14)15)12(16)13(17-10)8(2)3/h6-7H,4-5H2,1-3H3,(H,14,15)

> <INCHI_KEY>
NPEVDKHQEYSYTP-UHFFFAOYSA-N

> <FORMULA>
C13H16O4

> <MOLECULAR_WEIGHT>
236.267

> <EXACT_MASS>
236.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.76553510608864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[4-oxo-5-(propan-2-ylidene)-2-propyl-4,5-dihydrofuran-3-yl]prop-2-enoic acid

> <JCHEM_LOGP>
2.2425972606666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6291581820002285

> <JCHEM_PKA_STRONGEST_BASIC>
-5.388840947174074

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
67.14260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)
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PDB for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   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       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.379   1.096   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.700   2.602   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.524   0.066   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   17  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   17                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13    4                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

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3D PDB for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)
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SMILES for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)
CCCC1=C(C=CC(O)=O)C(=O)C(O1)=C(C)C
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INCHI for NP0243494 (3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid)
InChI=1S/C13H16O4/c1-4-5-10-9(6-7-11(14)15)12(16)13(17-10)8(2)3/h6-7H,4-5H2,1-3H3,(H,14,15)
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View in JSmol
Synonyms
ValueSource
3-[4-oxo-5-(Propan-2-ylidene)-2-propyl-4,5-dihydrofuran-3-yl]prop-2-enoateGenerator
Chemical FormulaC13H16O4
Average Mass236.2670 Da
Monoisotopic Mass236.10486 Da
IUPAC Name3-[4-oxo-5-(propan-2-ylidene)-2-propyl-4,5-dihydrofuran-3-yl]prop-2-enoic acid
Traditional Name3-[4-oxo-5-(propan-2-ylidene)-2-propylfuran-3-yl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
CCCC1=C(C=CC(O)=O)C(=O)C(O1)=C(C)C
InChI Identifier
InChI=1S/C13H16O4/c1-4-5-10-9(6-7-11(14)15)12(16)13(17-10)8(2)3/h6-7H,4-5H2,1-3H3,(H,14,15)
InChI KeyNPEVDKHQEYSYTP-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lactobacillus helveticusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentFuranones  
Alternative Parents
Substituents
  • 3-furanone
    • 

  • Vinylogous ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.24ChemAxon
pKa (Strongest Acidic)4.63ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.14 m³·mol⁻¹ChemAxon
Polarizability25.77 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162964774  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]