NP-MRD: Showing NP-Card for 4-hydroxyphenylglycine (NP0190724)

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Record Information

Version

2.0

Created at

2022-09-04 07:27:00 UTC

Updated at

2022-09-04 07:27:00 UTC

NP-MRD ID

NP0190724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxyphenylglycine

Description

4-Hydroxyphenylglycine, also known as PHPG or oxfenicine, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 4-Hydroxyphenylglycine is a very strong basic compound (based on its pKa). 4-hydroxyphenylglycine is found in Streptomyces fungicidicus. A glycine molecule carrying a 4-hydroxyphenyl substituent.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
Amino(4-hydroxyphenyl)ethanoic acid	ChEBI
p-Hydroxyphenylglycine	ChEBI
Para-hydroxyphenylglycine	ChEBI
PHPG	ChEBI
Amino(4-hydroxyphenyl)ethanoate	Generator
Oxfenicine	MeSH
4-Hydroxyphenylglycine hydrochloride, (R)-isomer	MeSH
4-Hydroxyphenylglycine perchlorate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine hydrobromide, (+-)-isomer	MeSH
(R,S)-3HPG	MeSH
4-Hydroxyphenylglycine, monosodium salt	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomer	MeSH
D-p-Hydroxyphenylglycine	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, monosodium salt, (R)-isomer	MeSH
4-Hydroxyphenylglycine, (S)-isomer	MeSH
L-4-Hydroxyphenylglycine	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomer	MeSH
4-Hydroxyphenylglycine, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, (R)-isomer	MeSH
2-Amino-2-(4-hydroxyphenyl)acetate	Generator
4-Hydroxyphenylglycine	MeSH

Chemical Formula

C₈H₉NO₃

Average Mass

167.1640 Da

Monoisotopic Mass

167.05824 Da

IUPAC Name

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

Traditional Name

4-hydroxyphenylglycine

CAS Registry Number

Not Available

SMILES

NC(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)

InChI Key

LJCWONGJFPCTTL-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
Streptomyces fungicidicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxide
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxy-amino acid (CHEBI:50418 )
a small molecule (P-HYDROXY-D-PHENYLGLYCINE )

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)	8.57	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	16.18 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

DB02601

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

4-Hydroxyphenylglycine

METLIN ID

Not Available

PubChem Compound

92143

PDB ID

Not Available

ChEBI ID

50418

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxyphenylglycine (NP0190724)

MOL for NP0190724 (4-hydroxyphenylglycine)

3D MOL for NP0190724 (4-hydroxyphenylglycine)

3D SDF for NP0190724 (4-hydroxyphenylglycine)

3D-SDF for NP0190724 (4-hydroxyphenylglycine)

PDB for NP0190724 (4-hydroxyphenylglycine)

3D PDB for NP0190724 (4-hydroxyphenylglycine)

SMILES for NP0190724 (4-hydroxyphenylglycine)

INCHI for NP0190724 (4-hydroxyphenylglycine)

Structure for NP0190724 (4-hydroxyphenylglycine)

3D Structure for NP0190724 (4-hydroxyphenylglycine)