Showing NP-Card for trans-Cinnamic acid (NP0001281)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:16:49 UTC
NP-MRD IDNP0001281
Natural Product DOIhttps://doi.org/10.57994/0815
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-Cinnamic acid
DescriptionTrans-Cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. Trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. Outside of the human body, trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons, olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. Trans-Cinnamic acid has also been detected, but not quantified in several different foods, such as common oregano, pepper (spice), fennels, pomegranates, and european cranberries. This could make trans-cinnamic acid a potential biomarker for the consumption of these foods. Cinnamic acid has been shown to be a microbial metabolite; it can be found in Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas (PMID: 16349793 ). Trans-Cinnamic acid is a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001281 (trans-Cinnamic acid)

  Mrv1652309272007382D          

 11 11  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    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
  6  1  1  0  0  0  0
  1  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
M  END
Download

3D MOL for NP0001281 (trans-Cinnamic acid)

HMDB0000930
     RDKit          3D
trans-Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.3195   -1.0333    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -0.2120   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.9754   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091   -0.5317    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.3242   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506    0.1041    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.0648    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -1.2113    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2449    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247    0.9256   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0695   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    1.8639   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.4660    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2833   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.8739    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -2.1519    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.4403    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    1.6979   -0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    1.9862   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  6  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0001281 (trans-Cinnamic acid)

  Mrv1652309272007382D          

 11 11  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    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
  6  1  1  0  0  0  0
  1  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
M  END
> <DATABASE_ID>
NP0001281

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

> <INCHI_KEY>
WBYWAXJHAXSJNI-VOTSOKGWSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.1586

> <EXACT_MASS>
148.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.428464888087186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-phenylprop-2-enoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.13608626

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.509231934706283

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
43.0599

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnamic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001281 (trans-Cinnamic acid)

HMDB0000930
     RDKit          3D
trans-Cinnamic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.3195   -1.0333    0.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -0.2120   -0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206    0.9754   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0091   -0.5317    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.3242   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506    0.1041    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977   -1.0648    0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1615   -1.2113    0.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2449    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247    0.9256   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0695   -0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    1.8639   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -1.4660    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.2833   -0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.8739    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -2.1519    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -0.4403    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    1.6979   -0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8626    1.9862   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  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  6  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0001281 (trans-Cinnamic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.625   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.958   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.292   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.292  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.958  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.625  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.291   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.043   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.376   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.376   3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.710   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0001281 (trans-Cinnamic acid)

COMPND    HMDB0000930
HETATM    1  O1  UNL     1       4.319  -1.033   0.202  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.429  -0.212  -0.111  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.821   0.975  -0.694  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.009  -0.532   0.149  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.068   0.324  -0.175  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.351   0.104   0.039  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.798  -1.065   0.617  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.161  -1.211   0.793  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.062  -0.245   0.414  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.625   0.926  -0.165  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.270   1.070  -0.339  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.409   1.864  -0.540  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.749  -1.466   0.605  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.370   1.283  -0.645  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.116  -1.874   0.941  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.494  -2.152   1.256  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.122  -0.440   0.588  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.314   1.698  -0.471  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.863   1.986  -0.797  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for NP0001281 (trans-Cinnamic acid)

OC(=O)\C=C\C1=CC=CC=C1
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INCHI for NP0001281 (trans-Cinnamic acid)

InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
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Synonyms
Chemical FormulaC9H8O2
Average Mass148.1586 Da
Monoisotopic Mass148.05243 Da
IUPAC Name(2E)-3-phenylprop-2-enoic acid
Traditional Namecinnamic acid
CAS Registry Number140-10-3
SMILES
OC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Pleurocybella porrigensKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • 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 Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling Point298.00 to 300.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.55 mg/mLNot Available
LogP2.13Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000930
DrugBank IDNot Available
Phenol Explorer Compound ID549
FoodDB IDFDB031209
KNApSAcK IDC00000170
Chemspider ID392447
KEGG Compound IDC10438
BioCyc IDCPD-674
BiGG IDNot Available
Wikipedia LinkCinnamic_acid
METLIN ID5880
PubChem Compound444539
PDB IDNot Available
ChEBI ID35697
Good Scents IDrw1350711
References
General References
  1. Blanquet S, Meunier JP, Minekus M, Marol-Bonnin S, Alric M: Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment. Appl Environ Microbiol. 2003 May;69(5):2884-92. [PubMed:12732562 ]
  2. Sarkissian CN, Shao Z, Blain F, Peevers R, Su H, Heft R, Chang TM, Scriver CR: A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2339-44. [PubMed:10051643 ]
  3. Wahl HG, Hong Q, Stube D, Maier ME, Haring HU, Liebich HM: Simultaneous analysis of the di(2-ethylhexyl)phthalate metabolites 2-ethylhexanoic acid, 2-ethyl-3-hydroxyhexanoic acid and 2-ethyl-3-oxohexanoic acid in urine by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):213-9. [PubMed:11486831 ]
  4. Larue C, Munnich A, Charpentier C, Saudubray JM, Frezal J, Remy MH, Rivat C: An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase. Dev Pharmacol Ther. 1986;9(2):73-81. [PubMed:3956347 ]
  5. Olivera ER, Carnicero D, Jodra R, Minambres B, Garcia B, Abraham GA, Gallardo A, Roman JS, Garcia JL, Naharro G, Luengo JM: Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications. Environ Microbiol. 2001 Oct;3(10):612-8. [PubMed:11722541 ]
  6. Lee HS, Beon MS, Kim MK: Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J Agric Food Chem. 2001 Oct;49(10):4656-61. [PubMed:11600003 ]
  7. Douros JD, Frankenfeld JW: Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms. Appl Microbiol. 1968 Feb;16(2):320-5. doi: 10.1128/am.16.2.320-325.1968. [PubMed:16349793 ]