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Showing metabocard for cis-p-Coumaric acid (HMDB0030677)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:38:22 UTC
Update Date2023-02-21 17:19:39 UTC
HMDB IDHMDB0030677
Secondary Accession Numbers
  • HMDB30677
Metabolite Identification
Common Namecis-p-Coumaric acid
Descriptioncis-p-Coumaric acid, also known as cis-4-hydroxycinnamic acid, is a hydroxy derivative of cinnamic acid. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic indigo, and pharmaceuticals. There are three isomers of coumaric acid: o-coumaric acid, m-coumaric acid, and p-coumaric acid. These isomers differ by the position of the hydroxy substitution. p-Coumaric acid is the most abundant isomer in nature (Wikipedia). cis-p-Coumaric acid is found in coriander.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030677 (cis-p-Coumaric acid)

  Mrv1652306141920472D          

 12 12  0  0  0  0            999 V2000
 9999.970210000.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.795210000.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5083 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.223510000.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.5083 9999.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.255510000.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.541110000.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.826510000.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8265 9999.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5410 9998.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2555 9999.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1120 9998.7631    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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030677 (cis-p-Coumaric acid)

HMDB0030677
     RDKit          3D
cis-p-Coumaric acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    1.7652    1.0637    1.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303    0.5991    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491    0.9334    1.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978   -0.2189   -0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3905   -0.6733   -0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -0.5401   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -0.4513    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -0.1824    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748    0.0013    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0034    0.2691    0.4723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -0.0886   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -0.3499   -1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490    1.3424    0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4590   -0.4714   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965   -1.2871   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676   -0.6670    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230   -0.1221    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3766    1.2058    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826    0.0540   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -0.4168   -2.4458 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
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for HMDB0030677 (cis-p-Coumaric acid)

  Mrv1652306141920472D          

 12 12  0  0  0  0            999 V2000
 9999.970210000.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.795210000.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5083 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.223510000.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.5083 9999.1766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.255510000.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.541110000.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.826510000.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8265 9999.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5410 9998.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2555 9999.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1120 9998.7631    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  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1  6  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030677

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-

> <INCHI_KEY>
NGSWKAQJJWESNS-UTCJRWHESA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.28354396015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.832520938333333

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.514997250797075

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5022437581354073

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954717586543567

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
45.040800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-p-coumaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0030677 (cis-p-Coumaric acid)

HMDB0030677
     RDKit          3D
cis-p-Coumaric acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    1.7652    1.0637    1.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6303    0.5991    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9491    0.9334    1.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978   -0.2189   -0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3905   -0.6733   -0.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327   -0.5401   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -0.4513    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -0.1824    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6748    0.0013    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0034    0.2691    0.4723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -0.0886   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -0.3499   -1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490    1.3424    0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4590   -0.4714   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965   -1.2871   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676   -0.6670    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0230   -0.1221    2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3766    1.2058    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826    0.0540   -1.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6334   -0.4168   -2.4458 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
  9 11  1  0
 11 12  2  0
 12  6  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0030677 (cis-p-Coumaric acid)

HEADER    PROTEIN                                 14-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JUN-19         0                                  
HETATM    1  C   UNK     0    8666.6118667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.1518667.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.4828666.666   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8670.8178667.436   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.4828665.130   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.2778666.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.9438667.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6098666.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6098665.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.9438664.358   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.2778665.128   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8661.2768664.358   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   11    1                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0030677 (cis-p-Coumaric acid)

COMPND    HMDB0030677
HETATM    1  O1  UNL     1       1.765   1.064   1.536  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.630   0.599   0.799  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.949   0.933   1.173  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.498  -0.219  -0.365  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.391  -0.673  -0.842  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.033  -0.540  -0.392  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.406  -0.451   0.896  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.742  -0.182   1.162  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.675   0.001   0.172  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.003   0.269   0.472  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.252  -0.089  -1.144  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.945  -0.350  -1.406  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.549   1.342   0.469  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.459  -0.471  -0.891  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.497  -1.287  -1.771  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.268  -0.667   1.736  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.023  -0.122   2.216  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.377   1.206   0.591  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.983   0.054  -1.965  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.633  -0.417  -2.446  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   12
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   11
CONECT   10   18
CONECT   11   12   12   19
CONECT   12   20
END
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SMILES for HMDB0030677 (cis-p-Coumaric acid)

OC(=O)\C=C/C1=CC=C(O)C=C1
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INCHI for HMDB0030677 (cis-p-Coumaric acid)

InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Namecis-p-coumaric acid
CAS Registry Number4501-31-9
SMILES
OC(=O)\C=C/C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
InChI KeyNGSWKAQJJWESNS-UTCJRWHESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134 - 134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.79Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.142 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.0160-2.940 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002592
KNApSAcK IDC00038791
Chemspider ID1266072
KEGG Compound IDC06738
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549106
PDB IDNot Available
ChEBI ID17450
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .