NP-MRD: Showing NP-Card for 2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid (NP0324957)

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Record Information

Version

2.0

Created at

2022-09-12 05:20:54 UTC

Updated at

2022-09-12 05:20:55 UTC

NP-MRD ID

NP0324957

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid

Description

2-(Benzoylamino)-3-phenylpropanoic acid belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid is found in Penicillium brevicompactum. 2-(Benzoylamino)-3-phenylpropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    1.9789   -1.1070   -2.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6910   -0.5519   -1.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053   -0.0480   -0.8755 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545   -0.1300   -1.8809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7582   -1.0164   -1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348   -0.4540   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9781   -0.7447    1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5890   -0.2344    2.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6841    0.5885    2.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1526    0.8885    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327    0.3715   -0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132    1.2068   -2.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    2.2840   -1.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173    1.3562   -3.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051   -0.4427   -0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.9658   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9447   -0.8680    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -0.2696    1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.2415    2.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942    0.1526    1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    0.4111    0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007   -0.6474   -2.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -1.2539   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666   -2.0043   -1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -1.3890    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -0.4655    3.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1687    0.9932    3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110    1.5326    0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957    0.6030   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9256    1.3601   -4.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -1.4426   -1.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -1.2685    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5005   -0.1964    2.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535    0.7241    3.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    0.5797    1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 12  1  0
 12 13  2  0
 12  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 20 15  1  0
 14 30  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
  3 21  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv1533004231518492D          

 20 21  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 O   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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324957

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO3/c18-15(13-9-5-2-6-10-13)17-14(16(19)20)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,18)(H,19,20)

> <INCHI_KEY>
NPKISZUVEBESJI-UHFFFAOYSA-N

> <FORMULA>
C16H15NO3

> <MOLECULAR_WEIGHT>
269.3

> <EXACT_MASS>
269.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.985775167865377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-2-(phenylformamido)propanoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.7506360943333332

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.169688209350973

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.829533351947858

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3434900480284337

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
75.23060000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-(phenylformamido)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -3.080   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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-(Benzoylamino)-3-phenylpropionic acid	ChEBI
2-(Benzoylamino)-3-phenylpropionate	Generator
2-(Benzoylamino)-3-phenylpropanoate	Generator

Chemical Formula

C₁₆H₁₅NO₃

Average Mass

269.3000 Da

Monoisotopic Mass

269.10519 Da

IUPAC Name

3-phenyl-2-(phenylformamido)propanoic acid

Traditional Name

3-phenyl-2-(phenylformamido)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15NO3/c18-15(13-9-5-2-6-10-13)17-14(16(19)20)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,17,18)(H,19,20)

InChI Key

NPKISZUVEBESJI-UHFFFAOYSA-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
Penicillium brevicompactum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	2.24	ALOGPS
logP	2.75	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.23 m³·mol⁻¹	ChemAxon
Polarizability	27.99 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

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

273362

PDB ID

Not Available

ChEBI ID

90419

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid (NP0324957)

MOL for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

3D MOL for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

3D SDF for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

3D-SDF for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

PDB for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

3D PDB for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

SMILES for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

INCHI for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

Structure for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)

3D Structure for NP0324957 (2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanoic acid)