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Showing NP-Card for p-Coumaraldehyde (NP0002815)

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Record Information
Version1.0
Created at2020-11-23 19:41:08 UTC
Updated at2021-08-19 23:59:26 UTC
NP-MRD IDNP0002815
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Coumaraldehyde
Provided ByBMRBBMRB logo
DescriptionP-Coumaraldehyde belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. P-Coumaraldehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. p-Coumaraldehyde is found in Alpinia galanga , Aralia bipinnata, Broussonetia papyrifera, Canarium schweinfurthii, Carya cathayensis, Cucurbita maxima, Daphnia pulex, Ginkgo biloba, Sarcophyte sanguinea and Zanthoxylum ailanthoides. It was first documented in 2005 (PMID: 15930771). Based on a literature review very few articles have been published on p-Coumaraldehyde (PMID: 17984079) (PMID: 21627350) (PMID: 32472480) (PMID: 29676125).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002815 (p-Coumaraldehyde)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.5137   -1.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -0.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654    0.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600   -0.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2371    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425    0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937    0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3454   -1.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    1.0510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    1.8097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.1504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    2.1891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854    2.9479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2479   -0.2534    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -2.0793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971   -2.8381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D MOL for NP0002815 (p-Coumaraldehyde)

NP0002815
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    4.6202   -1.5378   -0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608   -0.5500   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951   -0.7419   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6014    0.3079   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    0.1985   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.3890    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463    1.4173   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.2111   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974    0.2233   -0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.9686   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.0093   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2905    0.4399    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9585   -1.7163   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    1.3155    0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    2.3515    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726    2.3645    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715    0.1861    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -1.9419   -0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -1.9391   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0002815 (p-Coumaraldehyde)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.5137   -1.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -0.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654    0.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1600   -0.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2371    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883    1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425    0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937    0.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3454   -1.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708    1.0510    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683    1.8097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.1504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    2.1891    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854    2.9479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2479   -0.2534    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -2.0793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971   -2.8381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
> <DATABASE_ID>
NP0002815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+

> <INCHI_KEY>
CJXMVKYNVIGQBS-OWOJBTEDSA-N

> <FORMULA>
C9H8O2

> <MOLECULAR_WEIGHT>
148.1586

> <EXACT_MASS>
148.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.47110437438849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)prop-2-enal

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.6739046859999995

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.047621026698712

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3310723745240765

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
44.1154

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-coumaraldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002815 (p-Coumaraldehyde)

NP0002815
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    4.6202   -1.5378   -0.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608   -0.5500   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951   -0.7419   -0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6014    0.3079   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    0.1985   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.3890    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463    1.4173   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.2111   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9974    0.2233   -0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8997   -0.9686   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068   -1.0093   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2905    0.4399    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9585   -1.7163   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414    1.3155    0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    2.3515    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726    2.3645    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4715    0.1861    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -1.9419   -0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284   -1.9391   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0002815 (p-Coumaraldehyde)

HEADER    PROTEIN                                 17-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-20         0                                  
HETATM    1  C   UNK     0      -3.354  -1.459   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.687  -0.689   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.021  -1.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.021  -2.999   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.688  -3.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.354  -2.999   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.355  -3.769   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.020  -0.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.686  -1.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.647  -0.689   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.981  -1.459   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002815 (p-Coumaraldehyde)

COMPND    NP0002815
HETATM    1  O1  UNL     1       4.620  -1.538  -0.064  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.861  -0.550  -0.027  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.395  -0.742  -0.053  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.601   0.308  -0.015  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.154   0.198  -0.037  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.587   1.389   0.009  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.946   1.417  -0.006  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.612   0.211  -0.069  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.997   0.223  -0.085  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.900  -0.969  -0.114  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.507  -1.009  -0.100  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.291   0.440   0.023  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.958  -1.716  -0.103  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.041   1.316   0.037  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.050   2.352   0.060  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.473   2.365   0.032  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.472   0.186   0.813  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.407  -1.942  -0.165  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.028  -1.939  -0.136  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   13
CONECT    4    5   14
CONECT    5    6    6   11
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   10
CONECT    9   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for NP0002815 (p-Coumaraldehyde)

OC1=CC=C(\C=C\C=O)C=C1
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INCHI for NP0002815 (p-Coumaraldehyde)

InChI=1S/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+
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View in JSmol
Synonyms
ValueSource
(2E)-3-(4-Hydroxyphenyl)acrylaldehydeChEBI
(e)-4-CoumaraldehydeChEBI
4-Hydroxycinnamyl aldehydeChEBI
p-HydroxycinnamaldehydeChEBI
trans-4-HydroxycinnamaldehydeChEBI
trans-p-HydroxycinnamaldehydeChEBI
HydroxycinnamaldehydeHMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenalHMDB
(e)-3-(4-Hydroxyphenyl)-2-propenalHMDB
(e)-3-(4-Hydroxyphenyl)acrylaldehydeHMDB
(e)-p-HydroxycinnamaldehydeHMDB
3-(4-Hydroxyphenyl)-2-propenalHMDB
4-CoumaraldehydeHMDB
4-HydroxycinnamaldehydeHMDB
CoumaraldehydeHMDB
p-Coumaroyl aldehydeHMDB
trans-p-CoumaraldehydeHMDB
p-CoumaraldehydeChEBI, KEGG
Chemical FormulaC9H8O2
Average Mass148.1586 Da
Monoisotopic Mass148.05243 Da
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enal
Traditional Namep-coumaraldehyde
CAS Registry NumberNot Available
SMILES
OC1=CC=C(\C=C\C=O)C=C1
InChI Identifier
InChI=1S/C9H8O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-7,11H/b2-1+
InChI KeyCJXMVKYNVIGQBS-OWOJBTEDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, DMSO, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alpinia galangaPlant
Arabidopsis thalianaKNApSAcK Database
Aralia bipinnataLOTUS Database
Broussonetia papyriferaLOTUS Database
Canarium schweinfurthiiLOTUS Database
Carica papayaKNApSAcK Database
Carya cathayensisLOTUS Database
Chamaecyparis formosensisKNApSAcK Database
Colchicum autmnaleKNApSAcK Database
Colchicum hierosolymitanumKNApSAcK Database
Colchicum tunicatumKNApSAcK Database
Cucurbita maximaLOTUS Database
Daphnia pulexLOTUS Database
Ginkgo bilobaLOTUS Database
Gloriosa superbaKNApSAcK Database
Ilex paraguariensisKNApSAcK Database
Medicago sativaKNApSAcK Database
Ocimum basilicumKNApSAcK Database
Ocimum sanctumKNApSAcK Database
Pelargonium reniformeKNApSAcK Database
Pinus radiataKNApSAcK Database
Pinus spp.KNApSAcK Database
Populus spp.KNApSAcK Database
Populus trichocarpaKNApSAcK Database
Sarcophyte sanguineaLOTUS Database
Spiraea formosanaKNApSAcK Database
Zanthoxylum ailanthoidesLOTUS Database
Zea maysKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamaldehydes
Sub ClassNot Available
Direct ParentCinnamaldehydes
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility21170 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.06ALOGPS
logP1.67ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.12 m³·mol⁻¹ChemAxon
Polarizability15.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040986
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020845
KNApSAcK IDC00031014
Chemspider ID556592
KEGG Compound IDC05608
BioCyc IDCOUMARALDEHYDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound641301
PDB IDNot Available
ChEBI ID28353
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Morikawa T, Ando S, Matsuda H, Kataoka S, Muraoka O, Yoshikawa M: Inhibitors of nitric oxide production from the rhizomes of Alpinia galanga: structures of new 8-9' linked neolignans and sesquineolignan. Chem Pharm Bull (Tokyo). 2005 Jun;53(6):625-30. doi: 10.1248/cpb.53.625. [PubMed:15930771 ]
  3. Banjerdpongchai R, Punyati P, Nakrob A, Pompimon W, Kongtawelert P: 4'-Hydroxycinnamaldehyde from Alpinia galanga (Linn.) induces human leukemic cell apoptosis via mitochondrial and endoplasmic reticulum stress pathways. Asian Pac J Cancer Prev. 2011;12(3):593-8. [PubMed:21627350 ]
  4. Liu W, Jiang Y, Wang C, Zhao L, Jin Y, Xing Q, Li M, Lv T, Qi H: Lignin synthesized by CmCAD2 and CmCAD3 in oriental melon (Cucumis melo L.) seedlings contributes to drought tolerance. Plant Mol Biol. 2020 Aug;103(6):689-704. doi: 10.1007/s11103-020-01018-7. Epub 2020 May 29. [PubMed:32472480 ]
  5. Wang MY, Zhan ZB, Xiong Y, Li XB: [Studies on liposoluble constituents from Momordicae Semen]. Zhongguo Zhong Yao Za Zhi. 2018 Mar;43(6):1175-1181. doi: 10.19540/j.cnki.cjcmm.2018.0042. [PubMed:29676125 ]