Hmdb loader

Showing metabocard for trans-Cinnamic acid (HMDB0000930)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:18 UTC
HMDB IDHMDB0000930
Secondary Accession Numbers
  • HMDB00930
Metabolite 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000930 (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 HMDB0000930 (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 HMDB0000930 (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>
HMDB0000930

> <DATABASE_NAME>
hmdb

> <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 HMDB0000930 (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 HMDB0000930 (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
Download

3D PDB for HMDB0000930 (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
Download

SMILES for HMDB0000930 (trans-Cinnamic acid)

OC(=O)\C=C\C1=CC=CC=C1
Download

INCHI for HMDB0000930 (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+
Download
View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
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
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular 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,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available135.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000542
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.869 +/- 1.14 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID549
FooDB IDFDB012052
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1350711
References
Synthesis ReferenceZhu, Min; Shentu, Chao; Zhou, Zhong Shi. Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts. Chinese Chemical Letters (2007), 18(3), 272-274.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
trans-Cinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-phenylprop-2-enoyl]oxy}oxane-2-carboxylic aciddetails