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

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Record Information

Version

2.0

Created at

2022-09-08 01:48:39 UTC

Updated at

2022-09-08 01:48:40 UTC

NP-MRD ID

NP0259815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

d-4-hydroxyphenylglycine

Description

D-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. d-4-hydroxyphenylglycine was first documented in 2009 (PMID: 20140718). D-4-hydroxyphenylglycine is a very strong basic compound (based on its pKa) (PMID: 22307823) (PMID: 22515657).

Structure

MOL 3D MOL SDF PDB SMILES InChI

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

View in JSmol

Synonyms

Value	Source
(R)-alpha-Amino-4-hydroxybenzeneacetic acid	ChEBI
4-HYDROXYPHENYLGLYCINE	ChEBI
D-N-(4-Hydroxyphenyl)glycine	ChEBI
(AlphaR)-alpha-amino-4-hydroxybenzeneacetic acid	Kegg
(R)-a-Amino-4-hydroxybenzeneacetate	Generator
(R)-a-Amino-4-hydroxybenzeneacetic acid	Generator
(R)-alpha-Amino-4-hydroxybenzeneacetate	Generator
(R)-Α-amino-4-hydroxybenzeneacetate	Generator
(R)-Α-amino-4-hydroxybenzeneacetic acid	Generator
(AlphaR)-a-amino-4-hydroxybenzeneacetate	Generator
(AlphaR)-a-amino-4-hydroxybenzeneacetic acid	Generator
(AlphaR)-alpha-amino-4-hydroxybenzeneacetate	Generator
(AlphaR)-α-amino-4-hydroxybenzeneacetate	Generator
(AlphaR)-α-amino-4-hydroxybenzeneacetic acid	Generator
(2R)-amino(4-Hydroxyphenyl)ethanoate	Generator
4-Hydroxyphenylglycine, (R)-isomer	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, monosodium salt	MeSH
(R,S)-3HPG	MeSH
4-Hydroxyphenylglycine hydrochloride, (R)-isomer	MeSH
4-Hydroxyphenylglycine, (+-)-isomer	MeSH
D-P-Hydroxyphenylglycine	MeSH
Oxfenicine	MeSH
P-Hydroxyphenylglycine	MeSH
4-Hydroxyphenylglycine hydrobromide, (+-)-isomer	MeSH
4-Hydroxyphenylglycine perchlorate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, (S)-isomer	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomer	MeSH
4-Hydroxyphenylglycine, monosodium salt, (R)-isomer	MeSH
L-4-Hydroxyphenylglycine	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomer	MeSH

Chemical Formula

C₈H₉NO₃

Average Mass

167.1620 Da

Monoisotopic Mass

167.05824 Da

IUPAC Name

(2R)-2-amino-2-(4-hydroxyphenyl)acetic acid

Traditional Name

D-4-hydroxyphenylglycine

CAS Registry Number

Not 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 Key

LJCWONGJFPCTTL-SSDOTTSWSA-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
Apis cerana	LOTUS Database	35616633
Daphnia pulex	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

4-hydroxyphenylglycine (CHEBI:15695 )

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	-2.4	ALOGPS
logP	-1.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	8.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.34 m³·mol⁻¹	ChemAxon
Polarizability	16.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB04308

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03493

BioCyc ID

D-4-HYDROXYPHENYLGLYCINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89853

PDB ID

Not Available

ChEBI ID

15695

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
LOTUS database [Link]

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

MOL for NP0259815 (d-4-hydroxyphenylglycine)

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

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

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

PDB for NP0259815 (d-4-hydroxyphenylglycine)

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

SMILES for NP0259815 (d-4-hydroxyphenylglycine)

INCHI for NP0259815 (d-4-hydroxyphenylglycine)

Structure for NP0259815 (d-4-hydroxyphenylglycine)

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