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Showing NP-Card for d-4-hydroxyphenylglycine (NP0259815)

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Record Information
Version1.0
Created at2022-09-08 01:48:39 UTC
Updated at2022-09-08 01:48:40 UTC
NP-MRD IDNP0259815
Secondary Accession NumbersNone
Natural Product Identification
Common Named-4-hydroxyphenylglycine
DescriptionD-4-hydroxyphenylglycine belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. d-4-hydroxyphenylglycine is found in Apis cerana and Daphnia pulex. It was first documented in 1995 (PMID: 7716788). D-4-hydroxyphenylglycine is a very strong basic compound (based on its pKa) (PMID: 20140718) (PMID: 22307823) (PMID: 22515657).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0259815 (d-4-hydroxyphenylglycine)


  Mrv0541 05041402422D          

 13 13  0  0  1  0            999 V2000
    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   -0.4125    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
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   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
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  6  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  2  0  0  0  0
  7 13  1  6  0  0  0
M  END
Download

3D MOL for NP0259815 (d-4-hydroxyphenylglycine)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.0630   -1.5852   -0.7882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753   -0.2061   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5039    0.5008    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3814   -0.1733    0.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    1.8325    0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322   -0.0506   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3700   -0.8324    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7174   -0.6834    0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    0.2490    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550    0.4103    0.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9013    1.0314   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    0.8837   -0.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013   -2.1948   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4585   -1.9793    0.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    0.3321   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852    2.2037    1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2254   -1.5707    1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -1.2990    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173   -0.1308    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.7707   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699    1.4913   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  2 15  1  6
  1 13  1  0
  1 14  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0259815 (d-4-hydroxyphenylglycine)


  Mrv0541 05041402422D          

 13 13  0  0  1  0            999 V2000
    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   -0.4125    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
    0.7145   -1.2375    0.0000 C   0  0  2  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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   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
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  6  0  0  0
 10  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  2  0  0  0  0
  7 13  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0259815

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m1/s1

> <INCHI_KEY>
LJCWONGJFPCTTL-SSDOTTSWSA-N

> <FORMULA>
C8H9NO3

> <MOLECULAR_WEIGHT>
167.162

> <EXACT_MASS>
167.058243159

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.103775281757585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-1.7768551612088122

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.588308589045008

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7398199298342538

> <JCHEM_PKA_STRONGEST_BASIC>
8.745202161521709

> <JCHEM_POLAR_SURFACE_AREA>
83.55000000000001

> <JCHEM_REFRACTIVITY>
42.3422

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-4-hydroxyphenylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0259815 (d-4-hydroxyphenylglycine)

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PDB for NP0259815 (d-4-hydroxyphenylglycine)
HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    5                                                       
CONECT    2    4    5                                                       
CONECT    3    1    6                                                       
CONECT    4    2    6                                                       
CONECT    5    1    2    7                                                  
CONECT    6    3    4   10                                                  
CONECT    7    5    8    9   13                                             
CONECT    8    7   11   12                                                  
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0259815 (d-4-hydroxyphenylglycine)
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SMILES for NP0259815 (d-4-hydroxyphenylglycine)
[H][C@](N)(C(O)=O)C1=CC=C(O)C=C1
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INCHI for NP0259815 (d-4-hydroxyphenylglycine)
InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m1/s1
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View in JSmol
Synonyms
ValueSource
(R)-alpha-Amino-4-hydroxybenzeneacetic acidChEBI
4-HYDROXYPHENYLGLYCINEChEBI
D-N-(4-Hydroxyphenyl)glycineChEBI
(AlphaR)-alpha-amino-4-hydroxybenzeneacetic acidKegg
(R)-a-Amino-4-hydroxybenzeneacetateGenerator
(R)-a-Amino-4-hydroxybenzeneacetic acidGenerator
(R)-alpha-Amino-4-hydroxybenzeneacetateGenerator
(R)-Α-amino-4-hydroxybenzeneacetateGenerator
(R)-Α-amino-4-hydroxybenzeneacetic acidGenerator
(AlphaR)-a-amino-4-hydroxybenzeneacetateGenerator
(AlphaR)-a-amino-4-hydroxybenzeneacetic acidGenerator
(AlphaR)-alpha-amino-4-hydroxybenzeneacetateGenerator
(AlphaR)-α-amino-4-hydroxybenzeneacetateGenerator
(AlphaR)-α-amino-4-hydroxybenzeneacetic acidGenerator
(2R)-amino(4-Hydroxyphenyl)ethanoateGenerator
4-Hydroxyphenylglycine, (R)-isomerMeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomerMeSH
4-Hydroxyphenylglycine, monosodium saltMeSH
(R,S)-3HPGMeSH
4-Hydroxyphenylglycine hydrochloride, (R)-isomerMeSH
4-Hydroxyphenylglycine, (+-)-isomerMeSH
D-P-HydroxyphenylglycineMeSH
OxfenicineMeSH
P-HydroxyphenylglycineMeSH
4-Hydroxyphenylglycine hydrobromide, (+-)-isomerMeSH
4-Hydroxyphenylglycine perchlorate, (+-)-isomerMeSH
4-Hydroxyphenylglycine, (S)-isomerMeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomerMeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomerMeSH
4-Hydroxyphenylglycine, monosodium salt, (R)-isomerMeSH
L-4-HydroxyphenylglycineMeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomerMeSH
Chemical FormulaC8H9NO3
Average Mass167.1620 Da
Monoisotopic Mass167.05824 Da
IUPAC Name(2R)-2-amino-2-(4-hydroxyphenyl)acetic acid
Traditional NameD-4-hydroxyphenylglycine
CAS Registry NumberNot Available
SMILES
[H][C@](N)(C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m1/s1
InChI KeyLJCWONGJFPCTTL-SSDOTTSWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Daphnia pulexLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Aralkylamine
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • 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-2.4ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)8.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.34 m³·mol⁻¹ChemAxon
Polarizability16.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04308  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03493  
BioCyc IDD-4-HYDROXYPHENYLGLYCINE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89853  
PDB IDNot Available
ChEBI ID15695  
Good Scents IDNot Available
References
General References
  1. Yu H, Yang S, Jiang W, Yang Y: Efficient biocatalytic production of D-4-hydroxyphenylglycine by whole cells of recombinant Ralstonia pickettii. Folia Microbiol (Praha). 2009 Nov;54(6):509-15. doi: 10.1007/s12223-009-0073-y. Epub 2010 Feb 7. [PubMed:20140718  ] 
  2. Kastner S, Muller S, Natesan L, Konig GM, Guthke R, Nett M: 4-Hydroxyphenylglycine biosynthesis in Herpetosiphon aurantiacus: a case of gene duplication and catalytic divergence. Arch Microbiol. 2012 Jun;194(6):557-66. doi: 10.1007/s00203-012-0789-y. Epub 2012 Feb 4. [PubMed:22307823  ] 
  3. Jariyachawalid K, Laowanapiban P, Meevootisom V, Wiyakrutta S: Effective enhancement of Pseudomonas stutzeri D-phenylglycine aminotransferase functional expression in Pichia pastoris by co-expressing Escherichia coli GroEL-GroES. Microb Cell Fact. 2012 Apr 19;11:47. doi: 10.1186/1475-2859-11-47. [PubMed:22515657  ] 
  4. Mayorga C, Obispo T, Jimeno L, Blanca M, Moscoso del Prado J, Carreira J, Garcia JJ, Juarez C: Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies. Toxicology. 1995 Mar 31;97(1-3):225-34. doi: 10.1016/0300-483x(94)02983-2. [PubMed:7716788  ] 
  5. LOTUS database [Link]