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Showing NP-Card for Cinnamylideneacetic acid (NP0140127)

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Record Information
Version2.0
Created at2022-06-29 20:47:15 UTC
Updated at2022-06-29 20:47:15 UTC
NP-MRD IDNP0140127
Secondary Accession NumbersNone
Natural Product Identification
Common NameCinnamylideneacetic acid
Description5-Phenylpenta-2,4-dienoic acid, also known as beta-styrylacrylic acid, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Cinnamylideneacetic acid was first documented in 2015 (PMID: 26347954). Based on a literature review a small amount of articles have been published on 5-Phenylpenta-2,4-dienoic acid (PMID: 32018089) (PMID: 32905916).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140127 (Cinnamylideneacetic acid)


  Mrv1652306292222472D          

 13 13  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.8250    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    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  4  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0140127 (Cinnamylideneacetic acid)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    5.1749   -2.4810   -0.6873 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260   -1.4857   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -0.2685   -0.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129   -1.6609   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.9360   -0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9192   -0.1224   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3532   -0.6308   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    0.1639    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565   -0.3829   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9443    0.3321   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    1.5763    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7068    2.1511    0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5335    1.4454    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392   -0.0797   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6184   -2.7461   -0.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812    0.1626   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8907    0.9356    0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745   -1.6917   -0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -1.3916   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9006   -0.1134   -0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8161    2.1633    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007    3.1409    1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6322    1.9195    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0140127 (Cinnamylideneacetic acid)


  Mrv1652306292222472D          

 13 13  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.8250    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    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  4  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140127

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H,(H,12,13)/b8-4+,9-5+

> <INCHI_KEY>
FEIQOMCWGDNMHM-KBXRYBNXSA-N

> <FORMULA>
C11H10O2

> <MOLECULAR_WEIGHT>
174.199

> <EXACT_MASS>
174.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.86224636774853

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-phenylpenta-2,4-dienoic acid

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.663301933333333

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.831565396057411

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
53.37850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-5-phenylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0140127 (Cinnamylideneacetic acid)

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PDB for NP0140127 (Cinnamylideneacetic acid)
HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0140127 (Cinnamylideneacetic acid)
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SMILES for NP0140127 (Cinnamylideneacetic acid)
OC(=O)\C=C\C=C\C1=CC=CC=C1
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INCHI for NP0140127 (Cinnamylideneacetic acid)
InChI=1S/C11H10O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H,(H,12,13)/b8-4+,9-5+
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View in JSmol
Synonyms
ValueSource
5-Phenylpenta-2,4-dienoateGenerator
beta-Styrylacrylic acid, (e,Z)-isomerMeSH
beta-Styrylacrylic acid, monosodium salt, (e,e)-isomerMeSH
beta-Styrylacrylic acidMeSH
beta-Styrylacrylic acid, (Z,e)-isomerMeSH
beta-Styrylacrylic acid, (e,e)-isomerMeSH
beta-Styrylacrylic acid, monosodium salt, (e,Z)-isomerMeSH
Chemical FormulaC11H10O2
Average Mass174.1990 Da
Monoisotopic Mass174.06808 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H10O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H,(H,12,13)/b8-4+,9-5+
InChI KeyFEIQOMCWGDNMHM-KBXRYBNXSA-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 styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassStyrenes  
Direct ParentStyrenes  
Alternative Parents
Substituents
  • Medium-chain fatty acid
    • 

  • Styrene
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1266389  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549512  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Shindo M, Makigawa S, Matsumoto K, Iwata T, Wasano N, Kano A, Morita MT, Fujii Y: Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism. Phytochemistry. 2020 Apr;172:112287. doi: 10.1016/j.phytochem.2020.112287. Epub 2020 Feb 1. [PubMed:32018089  ] 
  2. Shindo M, Makigawa S, Kodama K, Sugiyama H, Matsumoto K, Iwata T, Wasano N, Kano A, Morita MT, Fujii Y: Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity. Phytochemistry. 2020 Nov;179:112508. doi: 10.1016/j.phytochem.2020.112508. Epub  2020 Sep 6. [PubMed:32905916  ] 
  3. Catchpole O, Mitchell K, Bloor S, Davis P, Suddes A: Antiproliferative activity of New Zealand propolis and phenolic compounds vs human colorectal adenocarcinoma cells. Fitoterapia. 2015 Oct;106:167-74. doi: 10.1016/j.fitote.2015.09.004. Epub 2015  Sep 6. [PubMed:26347954  ]