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Showing NP-Card for trans-2-Methoxycinnamaldehyde (NP0046547)

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Record Information
Version2.0
Created at2022-03-17 20:07:42 UTC
Updated at2022-03-17 20:07:42 UTC
NP-MRD IDNP0046547
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-2-Methoxycinnamaldehyde
DescriptionCassiastearoptene, also known as fema 3181, 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. Cassiastearoptene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cassiastearoptene has been detected, but not quantified in, chinese cinnamons. trans-2-Methoxycinnamaldehyde is found in Cinnamomum zeylanicum and Illicium verum. This could make cassiastearoptene a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046547 (trans-2-Methoxycinnamaldehyde)


  Mrv0541 05061307232D          

 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   -0.4125    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
   -1.4289    0.8250    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
   -0.7145    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
   -2.1434    1.2375    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   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
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for NP0046547 (trans-2-Methoxycinnamaldehyde)

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3D SDF for NP0046547 (trans-2-Methoxycinnamaldehyde)

  Mrv0541 05061307232D          

 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   -0.4125    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
   -1.4289    0.8250    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
   -0.7145    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
   -2.1434    1.2375    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   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
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+

> <INCHI_KEY>
KKVZAVRSVHUSPL-GQCTYLIASA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.1852

> <EXACT_MASS>
162.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.30026113482849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2-methoxyphenyl)prop-2-enal

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.8197987419999997

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.496182148588888

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
48.59770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxycinnamaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046547 (trans-2-Methoxycinnamaldehyde)
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PDB for NP0046547 (trans-2-Methoxycinnamaldehyde)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2    9                                                       
CONECT    6    4    9                                                       
CONECT    7    3   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5    6   10                                                  
CONECT   10    7    9   12                                                  
CONECT   11    8                                                            
CONECT   12    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0046547 (trans-2-Methoxycinnamaldehyde)
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SMILES for NP0046547 (trans-2-Methoxycinnamaldehyde)
COC1=CC=CC=C1\C=C\C=O
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INCHI for NP0046547 (trans-2-Methoxycinnamaldehyde)
InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+
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View in JSmol
Synonyms
ValueSource
2-Methoxy cinnamaldehydeHMDB
2-MethoxycinnamaldehydeHMDB
Ortho-methoxycinnamaldehydeHMDB
(2E)-3-(2-Methoxyphenyl)-2-propenalHMDB
(2E)-3-(2-Methoxyphenyl)acrylaldehydeHMDB
2'-MethoxycinnamaldehydeHMDB
2-Methoxycinnamic aldehydeHMDB
3-(2-Methoxyphenyl)-(2E)-2-propenalHMDB
3-(2-Methoxyphenyl)-2-propenalHMDB
3-O-Methoxyphenyl-2-propenalHMDB
beta -(O-Methoxyphenyl)acroleinHMDB
beta-(O-Methoxyphenyl)acroleinHMDB
beta-O-Methoxyphenyl acroleinHMDB
FEMA 3181HMDB
O-Methoxy cinnamaldehydeHMDB
O-Methoxy-cinnamaldehydeHMDB
O-MethoxycinnamaldehydeHMDB
O-Methoxycinnamic aldehydeHMDB
O-Methoxycinnamicaldehyde crystalsHMDB
Ortho methoxy cinnamic aldehydeHMDB
Chemical FormulaC10H10O2
Average Mass162.1852 Da
Monoisotopic Mass162.06808 Da
IUPAC Name(2E)-3-(2-methoxyphenyl)prop-2-enal
Traditional Name2-methoxycinnamaldehyde
CAS Registry Number1504-74-1
SMILES
COC1=CC=CC=C1\C=C\C=O
InChI Identifier
InChI=1S/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+
InChI KeyKKVZAVRSVHUSPL-GQCTYLIASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamomum aromaticumFooDB
Cinnamomum verumPlant
Illicium verumLOTUS 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
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Styrene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated aldehyde
    • 

  • Enal
    • 

  • Ether
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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
logP2.05ALOGPS
logP1.82ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.6 m³·mol⁻¹ChemAxon
Polarizability17.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033830  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004883  
KNApSAcK IDNot Available
Chemspider ID556589  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound641298  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available