NP-MRD: Showing NP-Card for Cinnamyl anthranilate (NP0337693)

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Record Information

Version

2.0

Created at

2024-09-11 11:58:18 UTC

Updated at

2024-09-11 11:58:18 UTC

NP-MRD ID

NP0337693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinnamyl anthranilate

Description

Cinnamyl anthranilate, also known as cinnamyl 2-aminobenzoate or fema 2295, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Cinnamyl anthranilate is a moderately basic compound (based on its pKa). Cinnamyl anthranilate is a balsam, fruity, and grape tasting compound. Outside of the human body,.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312342D          

 19 20  0  0  0  0            999 V2000
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6-

> <INCHI_KEY>
GABQNAFEZZDSCM-TWGQIWQCSA-N

> <FORMULA>
C16H15NO2

> <MOLECULAR_WEIGHT>
253.2958

> <EXACT_MASS>
253.110278729

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.083932977869598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.132185616666667

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.390839665845853

> <JCHEM_PKA_STRONGEST_BASIC>
2.146031644801402

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
77.7149

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.668  16.170   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    8                                                       
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    9   12                                                       
CONECT    7    2   13                                                       
CONECT    8    3   13                                                       
CONECT    9    6   13                                                       
CONECT   10    4   14                                                       
CONECT   11    5   15                                                       
CONECT   12    6   19                                                       
CONECT   13    7    8    9                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   17                                                  
CONECT   16   14   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Cinnamyl anthranilic acid	Generator
2-Aminobenzoic acid 3-phenyl-2-propenyl ester	HMDB
2-Propen-1-ol, 3-phenyl-, 1-(2-aminobenzoate)	HMDB
2-Propen-1-ol, 3-phenyl-, 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-ol 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-yl 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-yl anthranilate	HMDB
3-Phenyl-2-propenyl anthranilate	HMDB
3-Phenyl-2-propenylanthranilate	HMDB
Anthranilic acid, cinnamyl ester	HMDB
Benzoic acid, 2-amino-, 3-phenyl-2-propenyl ester	HMDB
Cinnamyl 2-aminobenzoate	HMDB
Cinnamyl alcohol, anthranilate	HMDB
Cinnamyl anthranylate	HMDB
Cinnamyl O-aminobenzoate	HMDB
Cinnamylester kyseliny anthranilove	HMDB
FEMA 2295	HMDB
(2Z)-3-Phenylprop-2-en-1-yl 2-aminobenzoic acid	Generator
3-Phenyl-2-propenyl-2-aminobenzoate	MeSH
Cinnamyl anthranilate	MeSH

Chemical Formula

C₁₆H₁₅NO₂

Average Mass

253.2958 Da

Monoisotopic Mass

253.11028 Da

IUPAC Name

(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

Traditional Name

(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

CAS Registry Number

Not Available

SMILES

NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6-

InChI Key

GABQNAFEZZDSCM-TWGQIWQCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Styrene
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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	3.54	ALOGPS
logP	4.13	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	19.39	ChemAxon
pKa (Strongest Basic)	2.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.71 m³·mol⁻¹	ChemAxon
Polarizability	28.08 Å³	ChemAxon
Number of Rings	2	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

HMDB0041319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021238

KNApSAcK ID

Not Available

Chemspider ID

30777557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54603882

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cinnamyl anthranilate (NP0337693)

MOL for NP0337693 (Cinnamyl anthranilate)

3D MOL for NP0337693 (Cinnamyl anthranilate)

3D SDF for NP0337693 (Cinnamyl anthranilate)

3D-SDF for NP0337693 (Cinnamyl anthranilate)

PDB for NP0337693 (Cinnamyl anthranilate)

3D PDB for NP0337693 (Cinnamyl anthranilate)

SMILES for NP0337693 (Cinnamyl anthranilate)

INCHI for NP0337693 (Cinnamyl anthranilate)

Structure for NP0337693 (Cinnamyl anthranilate)

3D Structure for NP0337693 (Cinnamyl anthranilate)