NP-MRD: Showing NP-Card for propyl cinnamate (NP0201832)

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Record Information

Version

2.0

Created at

2022-09-04 20:56:22 UTC

Updated at

2022-09-04 20:56:23 UTC

NP-MRD ID

NP0201832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

propyl cinnamate

Description

Propyl (2E)-3-phenylprop-2-enoate, also known as 3-phenylpropenoic acid propyl ester, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. propyl cinnamate is found in Artemisia salsoloides. Propyl (2E)-3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004251604002D          

 16 16  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201832

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h3-9H,2,10H2,1H3/b9-8+

> <INCHI_KEY>
OLLPXZHNCXACMM-CMDGGOBGSA-N

> <FORMULA>
C12H14O2

> <MOLECULAR_WEIGHT>
190.242

> <EXACT_MASS>
190.099379691

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.789354936878443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
propyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
3.3946439989999995

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.808933917470716

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.101600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propyl cinnamate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.338   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.672   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0      14.670   0.770   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      13.337   4.620   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   10                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   11   15                                                  
CONECT    9    8   12   16                                                  
CONECT   10    2   14                                                       
CONECT   11    6    7    8                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   10   12                                                       
CONECT   15    8                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
3-Phenylpropenoic acid propyl ester	Kegg
3-Phenylpropenoate propyl ester	Generator
Propyl (2E)-3-phenylprop-2-enoic acid	Generator
Propyl (e)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₄O₂

Average Mass

190.2420 Da

Monoisotopic Mass

190.09938 Da

IUPAC Name

propyl (2E)-3-phenylprop-2-enoate

Traditional Name

propyl cinnamate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)OCCC

InChI Identifier

InChI=1S/C12H14O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h3-9H,2,10H2,1H3/b9-8+

InChI Key

OLLPXZHNCXACMM-CMDGGOBGSA-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
Artemisia salsoloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkyl cinnamate (CHEBI:8501 )

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	3.43	ALOGPS
logP	3.39	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.1 m³·mol⁻¹	ChemAxon
Polarizability	21.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C06360

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5270647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for propyl cinnamate (NP0201832)

MOL for NP0201832 (propyl cinnamate)

3D MOL for NP0201832 (propyl cinnamate)

3D SDF for NP0201832 (propyl cinnamate)

3D-SDF for NP0201832 (propyl cinnamate)

PDB for NP0201832 (propyl cinnamate)

3D PDB for NP0201832 (propyl cinnamate)

SMILES for NP0201832 (propyl cinnamate)

INCHI for NP0201832 (propyl cinnamate)

Structure for NP0201832 (propyl cinnamate)

3D Structure for NP0201832 (propyl cinnamate)