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Showing NP-Card for Phenylalanine (NP0044227)

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Record Information
Version1.0
Created at2022-01-23 19:49:31 UTC
Updated at2022-01-23 19:56:53 UTC
NP-MRD IDNP0044227
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylalanine
Description Phenylalanine is found in Allium cepa, Arabidopsis thaliana, Atractylodes japonica, Caenorhabditis elegans, Castanea sativa, Centipeda minima, Chlamydomonas reinhardtii, Claviceps purpurea, Colchicum trigynum, Daphnia magna, Glycine max, Hypholoma fasciculare, Kaempferia parviflora, Lates calcarifer, Lemna aequinoctialis, Glinus oppositifolius, Mycoplasma bovis, Panax ginseng, Paris fargesii, Platycodon grandiflorus, Pseudophryne corroboree, Pseudostellaria heterophylla, Saussurea medusa, Sinocrassula indica, Stellaria media, Synechococcus elongatus, Taraxacum formosanum and Zyzzya fuliginosa. It was first documented in 2007 (PMID: 17439666).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044227 (Phenylalanine)


  Mrv1652310071711412D          

 12 12  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    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
    0.7145    2.0625    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
Download

3D MOL for NP0044227 (Phenylalanine)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -1.5851   -1.1464    1.3367 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563   -0.7331    0.0140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7614   -1.0312   -0.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5235   -0.3849   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4778   -0.9868    0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6821   -0.3674    0.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620    0.8901   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231    1.5056   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145    0.8728   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2712    0.6881    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    1.2372   -1.0739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    1.4543    1.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -2.0790    1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796   -0.4255    1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -1.3123   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1445   -0.6894   -1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6471   -2.1299   -1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271   -1.9836    0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061   -0.8716    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    1.3807    0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386    2.4950   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915    1.3745   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9397    2.2427    1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 12  1  0
 10 11  2  0
  9  4  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0044227 (Phenylalanine)


  Mrv1652310071711412D          

 12 12  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    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
    0.7145    2.0625    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044227

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

> <INCHI_KEY>
COLNVLDHVKWLRT-UHFFFAOYSA-N

> <FORMULA>
C9H11NO2

> <MOLECULAR_WEIGHT>
165.1891

> <EXACT_MASS>
165.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.19809866016248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-phenylpropanoic acid

> <ALOGPS_LOGP>
-1.35

> <JCHEM_LOGP>
-1.184438468740489

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.469229772182635

> <JCHEM_PKA_STRONGEST_BASIC>
9.446936344396194

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
45.1163

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylalanin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0044227 (Phenylalanine)

Download
PDB for NP0044227 (Phenylalanine)
HEADER    PROTEIN                                 07-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-OCT-17         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    7    8                                                       
CONECT    7    4    5    6                                                  
CONECT    8    6    9   10                                                  
CONECT    9    8   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0044227 (Phenylalanine)
Download
SMILES for NP0044227 (Phenylalanine)
NC(CC1=CC=CC=C1)C(O)=O
Download
INCHI for NP0044227 (Phenylalanine)
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
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View in JSmol
Synonyms
ValueSource
alpha-Amino-beta-phenylpropionic acidChEBI
DL-PhenylalanineChEBI
FChEBI
FenilalaninaChEBI
PHEChEBI
PhenylalaninChEBI
a-Amino-b-phenylpropionateGenerator
a-Amino-b-phenylpropionic acidGenerator
alpha-Amino-beta-phenylpropionateGenerator
Α-amino-β-phenylpropionateGenerator
Α-amino-β-phenylpropionic acidGenerator
L-Isomer phenylalanineMeSH
EndorphenylMeSH
L-PhenylalanineMeSH
PhenylalanineMeSH
Phenylalanine, L isomerMeSH
Phenylalanine, L-isomerMeSH
Chemical FormulaC9H11NO2
Average Mass165.1891 Da
Monoisotopic Mass165.07898 Da
IUPAC Name2-amino-3-phenylpropanoic acid
Traditional Namephenylalanin
CAS Registry NumberNot Available
SMILES
NC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
InChI KeyCOLNVLDHVKWLRT-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaLOTUS Database
Arabidopsis thalianaLOTUS Database
Atractylodes japonicaLOTUS Database
Caenorhabditis elegansLOTUS Database
Castanea sativaLOTUS Database
Centipeda minimaLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Claviceps purpureaLOTUS Database
Colchicum trigynumLOTUS Database
Daphnia magnaLOTUS Database
Glycine maxLOTUS Database
Hypholoma fasciculareLOTUS Database
Kaempferia parvifloraLOTUS Database
Lates calcariferLOTUS Database
Lemna aequinoctialisLOTUS Database
Mollugo oppositifoliaLOTUS Database
Mycoplasmopsis bovisLOTUS Database
Panax ginsengLOTUS Database
Paris fargesiiLOTUS Database
Platycodon grandiflorusLOTUS Database
Pseudophryne corroboreeLOTUS Database
Pseudostellaria heterophyllaLOTUS Database
Saussurea medusaLOTUS Database
Sinocrassula indicaLOTUS Database
Stellaria mediaLOTUS Database
Synechococcus elongatusLOTUS Database
Taraxacum formosanumLOTUS Database
Zyzzya fuliginosaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentPhenylalanine and derivatives  
Alternative Parents
Substituents
  • Phenylalanine or derivatives
    • 

  • 3-phenylpropanoic-acid
    • 

  • Alpha-amino acid
    • 

  • Amphetamine or derivatives
    • 

  • Aralkylamine
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Primary amine
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013245  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02057  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylalanine  
METLIN IDNot Available
PubChem Compound994  
PDB IDNot Available
ChEBI ID28044  
Good Scents IDNot Available
References
General References
  1. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666  ] 
  2. Castro C, Sar F, Shaw WR, Mishima M, Miska EA, Griffin JL: A metabolomic strategy defines the regulation of lipid content and global metabolism by Delta9 desaturases in Caenorhabditis elegans. BMC Genomics. 2012 Jan 20;13:36. doi: 10.1186/1471-2164-13-36. [PubMed:22264337  ] 
  3. Socher E, Conrad M, Heger L, Paulsen F, Sticht H, Zunke F, Arnold P: Computational decomposition reveals reshaping of the SARS-CoV-2-ACE2 interface among viral variants expressing the N501Y mutation. J Cell Biochem. 2021 Dec;122(12):1863-1872. doi: 10.1002/jcb.30142. Epub 2021 Sep 13. [PubMed:34516024  ]