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Showing NP-Card for 2-methoxy-3-phenylprop-2-enal (NP0302353)

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Record Information
Version2.0
Created at2022-09-10 15:50:58 UTC
Updated at2022-09-10 15:50:58 UTC
NP-MRD IDNP0302353
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-methoxy-3-phenylprop-2-enal
DescriptionMethoxycinnamaldehyde 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. 2-methoxy-3-phenylprop-2-enal was first documented in 2021 (PMID: 34425473). Based on a literature review a small amount of articles have been published on methoxycinnamaldehyde (PMID: 35875567) (PMID: 35725014) (PMID: 35321499) (PMID: 34096157).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0302353 (2-methoxy-3-phenylprop-2-enal)


  Mrv1652309102217502D          

 12 12  0  0  0  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    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   -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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  2  0  0  0  0
  6  7  1  4  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
  7 12  1  0  0  0  0
M  END
Download

3D MOL for NP0302353 (2-methoxy-3-phenylprop-2-enal)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    3.9248   -0.8330   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -0.6230   -1.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.3460   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -0.2499    1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4822   -0.4277    1.7712 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -0.1724   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    0.1185   -0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946   -0.6225    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -0.2795    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    0.7811    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646    1.5027   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000    1.1896   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1791    0.0730    0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -0.9540   -1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8078   -1.7014    0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553   -0.0229    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704   -0.2586   -2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283   -1.4805    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2363   -0.8778    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4846    1.0390    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3556    2.3655   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1394    1.7800   -1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0302353 (2-methoxy-3-phenylprop-2-enal)


  Mrv1652309102217502D          

 12 12  0  0  0  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    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   -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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  2  0  0  0  0
  6  7  1  4  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
  7 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C=O)=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-12-10(8-11)7-9-5-3-2-4-6-9/h2-8H,1H3

> <INCHI_KEY>
KPNHONAEPLEAJL-UHFFFAOYSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.188

> <EXACT_MASS>
162.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.37960408533116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-3-phenylprop-2-enal

> <JCHEM_LOGP>
1.5716397156666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8746743782947775

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
48.85310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-3-phenylprop-2-enal

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0302353 (2-methoxy-3-phenylprop-2-enal)

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PDB for NP0302353 (2-methoxy-3-phenylprop-2-enal)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0302353 (2-methoxy-3-phenylprop-2-enal)
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SMILES for NP0302353 (2-methoxy-3-phenylprop-2-enal)
COC(C=O)=CC1=CC=CC=C1
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INCHI for NP0302353 (2-methoxy-3-phenylprop-2-enal)
InChI=1S/C10H10O2/c1-12-10(8-11)7-9-5-3-2-4-6-9/h2-8H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H10O2
Average Mass162.1880 Da
Monoisotopic Mass162.06808 Da
IUPAC Name2-methoxy-3-phenylprop-2-enal
Traditional Name2-methoxy-3-phenylprop-2-enal
CAS Registry NumberNot Available
SMILES
COC(C=O)=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O2/c1-12-10(8-11)7-9-5-3-2-4-6-9/h2-8H,1H3
InChI KeyKPNHONAEPLEAJL-UHFFFAOYSA-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 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
    • 

  • 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 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
logP1.57ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.85 m³·mol⁻¹ChemAxon
Polarizability17.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002728  
Chemspider ID3651800  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4452795  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Qian C, Jin L, Zhu L, Zhou Y, Chen J, Yang D, Xu X, Ding P, Li R, Zhao Z: Metabolomics-Driven Exploration of the Antibacterial Activity and Mechanism of 2-Methoxycinnamaldehyde. Front Microbiol. 2022 Jul 7;13:864246. doi: 10.3389/fmicb.2022.864246.  eCollection 2022. [PubMed:35875567  ] 
  2. Kim BS, Shin M, Kim KW, Ha KT, Bae SJ: NRF2 activation by 2-methoxycinnamaldehyde attenuates inflammatory responses in macrophages via enhancing autophagy flux. BMB Rep. 2022 Aug;55(8):407-412. doi: 10.5483/BMBRep.2022.55.8.065. [PubMed:35725014  ] 
  3. Xu D, Ai Q, Chen X, Wang Z, Wei H, Zhou L, Mei Z, Ge J: Metabonomics Study on Naotaifang Extract Alleviating Neuronal Apoptosis after Cerebral Ischemia-Reperfusion Injury. Evid Based Complement Alternat Med. 2022 Mar 14;2022:2112433. doi:  10.1155/2022/2112433. eCollection 2022. [PubMed:35321499  ] 
  4. Kim HJ, Kim H, Choi Y, Lee JH, Kim D, Lee SK, Park KS: Cinnamomum verum-derived O-methoxycinnamaldehyde prevents lipopolysaccharide-induced depressive-like behavior in mice via NFAT mRNA stability in T lymphocytes. Phytomedicine. 2021 Oct;91:153703. doi: 10.1016/j.phymed.2021.153703. Epub 2021  Aug 8. [PubMed:34425473  ] 
  5. Oka Y: Aromatic compounds that attract Meloidogyne species second-stage juveniles in soil. Pest Manag Sci. 2021 Oct;77(10):4288-4297. doi: 10.1002/ps.6506. Epub 2021 Jun  19. [PubMed:34096157  ] 
  6. LOTUS database [Link]