NP-MRD: Showing NP-Card for N-Acetyl-D-Phenyl alanine (NP0002754)

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Record Information

Version

1.0

Created at

2020-11-23 19:39:34 UTC

Updated at

2021-08-12 19:52:03 UTC

NP-MRD ID

NP0002754

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-D-Phenyl alanine

Provided By

BMRB

Description

N-acetyl-D-phenylalanine 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. N-acetyl-D-phenylalanine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N-Acetyl-D-Phenyl alanine is found in Daphnia pulex. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on N-acetyl-D-phenylalanine (PMID: 34029974) (PMID: 29509381) (PMID: 22721690) (PMID: 20424794).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    3.9684    1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    0.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -0.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    0.2880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470   -1.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0415   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042   -0.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2069    1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0211    2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6326    1.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794   -2.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711   -2.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6980   -3.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3569    1.3116    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5799    2.4468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360    3.2676    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1473    1.5769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7354   -1.6680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3526    0.9145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -1.8418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4131   -2.3701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1900   -1.2350    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5954    1.7375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2238    3.5748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469    2.4396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304   -5.0632    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 12  7  1  0
  1 16  1  1
  1 17  1  0
  1 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  1
  6 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
M  END
> <DATABASE_ID>
NP0002754

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=N[C@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m1/s1

> <INCHI_KEY>
CBQJSKKFNMDLON-SNVBAGLBSA-N

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.229

> <EXACT_MASS>
207.089543283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.184740077396512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-phenylpropanoic acid

> <JCHEM_LOGP>
1.7160657829999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.19188319786172

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.069788900413923

> <JCHEM_PKA_STRONGEST_BASIC>
1.4187829961808711

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
55.08180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-acetyl-D-phenylalanine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       1.334   8.470   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7    9   10                                                       
CONECT    8    1   12   13                                                  
CONECT    9    5    6    7                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10   14   15                                                  
CONECT   12    8   10                                                       
CONECT   13    8                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    NP0002754
HETATM    1  C1  UNL     1      -2.482  -2.098  -1.256  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.363  -0.743  -0.688  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.402  -0.174   0.006  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.279  -0.088  -0.844  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.026   1.237  -0.346  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.400   1.604  -0.775  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.362   0.619  -0.187  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.702  -0.529  -0.872  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.581  -1.473  -0.384  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.141  -1.242   0.855  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.825  -0.110   1.564  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.941   0.817   1.047  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.126   1.275   1.132  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.402   0.221   1.747  1.00  0.00           O  
HETATM   15  O3  UNL     1      -0.914   2.474   1.809  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.490  -2.293  -1.704  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.246  -2.903  -0.510  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.724  -2.227  -2.064  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.030  -0.685   0.607  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.698   2.007  -0.764  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.463   1.641  -1.879  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.668   2.598  -0.382  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.242  -0.677  -1.843  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.818  -2.356  -0.954  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.825  -1.979   1.232  1.00  0.00           H  
HETATM   26  H11 UNL     1       3.263   0.073   2.535  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.715   1.688   1.622  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.764   3.324   1.296  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    4
CONECT    3   19
CONECT    4    5
CONECT    5    6   13   20
CONECT    6    7   21   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   14   15
CONECT   15   28
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃NO₃

Average Mass

207.2290 Da

Monoisotopic Mass

207.08954 Da

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-phenylpropanoic acid

Traditional Name

N-acetyl-D-phenylalanine

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m1/s1

InChI Key

CBQJSKKFNMDLON-SNVBAGLBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphnia pulex	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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acetyl-D-amino acid (CHEBI:28203 )
N-acyl-D-phenylalanine (CHEBI:28203 )
N-acetylphenylalanine (CHEBI:28203 )

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	1.72	ChemAxon
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	1.42	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.08 m³·mol⁻¹	ChemAxon
Polarizability	21.18 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

91422

KEGG Compound ID

C05620

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28203

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Li N, Mao W, Gao Y, Wang D, Song Z, Chen Z: Liquid chromatography-mass spectrometry based metabolic characterization of pleural effusion in patients with acquired EGFR-TKI resistance. J Pharm Biomed Anal. 2021 Aug 5;202:114147. doi: 10.1016/j.jpba.2021.114147. Epub 2021 May 18. [PubMed:34029974 ]
Hambardzumyan AA, Mkhitaryan AV, Paloyan AM, Dadayan SA, Saghyan AS: [Catalytic properties of aminoacylase of strain Rhodococcus armeniensis AM6.1]. Prikl Biokhim Mikrobiol. 2016 May-Jun;52(3):272-8. [PubMed:29509381 ]
Liu J, Asano Y, Ikoma K, Yamashita S, Hirose Y, Shimoyama T, Takahashi S, Nakayama T, Nishino T: Purification, characterization, and primary structure of a novel N-acyl-D-amino acid amidohydrolase from Microbacterium natoriense TNJL143-2. J Biosci Bioeng. 2012 Oct;114(4):391-7. doi: 10.1016/j.jbiosc.2012.05.015. Epub 2012 Jun 20. [PubMed:22721690 ]
Ito A, Ishizaka S, Kitamura N: A ratiometric TICT-type dual fluorescent sensor for an amino acid. Phys Chem Chem Phys. 2010 Jul 7;12(25):6641-9. doi: 10.1039/b924176k. Epub 2010 Apr 21. [PubMed:20424794 ]

Showing NP-Card for N-Acetyl-D-Phenyl alanine (NP0002754)

MOL for NP0002754 (N-Acetyl-D-Phenyl alanine)

3D MOL for NP0002754 (N-Acetyl-D-Phenyl alanine)

3D SDF for NP0002754 (N-Acetyl-D-Phenyl alanine)

3D-SDF for NP0002754 (N-Acetyl-D-Phenyl alanine)

PDB for NP0002754 (N-Acetyl-D-Phenyl alanine)

3D PDB for NP0002754 (N-Acetyl-D-Phenyl alanine)

SMILES for NP0002754 (N-Acetyl-D-Phenyl alanine)

INCHI for NP0002754 (N-Acetyl-D-Phenyl alanine)

Structure for NP0002754 (N-Acetyl-D-Phenyl alanine)

3D Structure for NP0002754 (N-Acetyl-D-Phenyl alanine)