NP-MRD: Showing NP-Card for (z)-4-methoxycinnamic acid (NP0190336)

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Record Information

Version

2.0

Created at

2022-09-04 06:58:56 UTC

Updated at

2022-09-04 06:58:56 UTC

NP-MRD ID

NP0190336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z)-4-methoxycinnamic acid

Description

5676-64-2 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. (z)-4-methoxycinnamic acid is found in Xylocarpus granatum. 5676-64-2 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09041212462D          

 15 15  0  0  0  0            999 V2000
   -0.0000    2.4750    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
    0.0000   -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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145    1.2375    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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
   -0.0000   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  2  2  0  0  0  0
  8  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  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  9  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190336

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4-

> <INCHI_KEY>
AFDXODALSZRGIH-DAXSKMNVSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.141946610106473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.978414994333333

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.609550182495488

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8239438706994795

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.523100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(4-methoxyphenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    5    8                                                       
CONECT    3    6    8                                                       
CONECT    4    7    8   14                                                  
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10   15                                                  
CONECT    8    2    3    4                                                  
CONECT    9    5    6   13                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1    9                                                       
CONECT   14    4                                                            
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxycinnamate, calcium salt	MeSH
4-Methoxycinnamate, aluminum salt	MeSH
4-Methoxycinnamate	MeSH
e-p-Methoxycinnamic acid	MeSH
4-Methoxycinnamate, zinc salt	MeSH
4-Methoxycinnamate, (Z)-isomer	MeSH
4-Methoxycinnamate, potassium salt	MeSH
4-Methoxycinnamic acid	MeSH
4-Methoxycinnamate, sodium salt	MeSH
4-Methoxycinnamate, zirconium salt	MeSH
4-Methoxycinnamate, magnesium salt	MeSH
4-Methoxycinnamate, (e)-isomer	MeSH
(Z)-3-(4-Methoxyphenyl)acrylate	Generator
(2Z)-3-(4-Methoxyphenyl)prop-2-enoate	Generator

Chemical Formula

C₁₀H₁₀O₃

Average Mass

178.1846 Da

Monoisotopic Mass

178.06299 Da

IUPAC Name

(2Z)-3-(4-methoxyphenyl)prop-2-enoic acid

Traditional Name

(2Z)-3-(4-methoxyphenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=CC=C(OC)C=C1)C(O)=O

InChI Identifier

InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4-

InChI Key

AFDXODALSZRGIH-DAXSKMNVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylocarpus granatum	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acids

Direct Parent

Cinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.37	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.52 m³·mol⁻¹	ChemAxon
Polarizability	18.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1550936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (z)-4-methoxycinnamic acid (NP0190336)

MOL for NP0190336 ((z)-4-methoxycinnamic acid)

3D MOL for NP0190336 ((z)-4-methoxycinnamic acid)

3D SDF for NP0190336 ((z)-4-methoxycinnamic acid)

3D-SDF for NP0190336 ((z)-4-methoxycinnamic acid)

PDB for NP0190336 ((z)-4-methoxycinnamic acid)

3D PDB for NP0190336 ((z)-4-methoxycinnamic acid)

SMILES for NP0190336 ((z)-4-methoxycinnamic acid)

INCHI for NP0190336 ((z)-4-methoxycinnamic acid)

Structure for NP0190336 ((z)-4-methoxycinnamic acid)

3D Structure for NP0190336 ((z)-4-methoxycinnamic acid)