D-4-Hydroxyphenylglycine

Details

• Internal ID: cefbc19b-1c14-43aa-bc38-c58c04547877
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > D-alpha-amino acids
• IUPAC Name: (2R)-2-amino-2-(4-hydroxyphenyl)acetic acid
• SMILES (Canonical): C1=CC(=CC=C1C(C(=O)O)N)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H](C(=O)O)N)O
• InChI: 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
• Popularity: 143 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16 g/mol
• Exact Mass: 167.058243149 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• D-4-Hydroxyphenylglycine
• D(-)-4-Hydroxyphenylglycine
• 4-Hydroxy-D-phenylglycine
• H-D-PHG(4-OH)-OH
• D-(-)-4-Hydroxyphenylglycine
• (R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETIC ACID
• D-N-(4-Hydroxyphenyl)glycine
• (2R)-2-amino-2-(4-hydroxyphenyl)acetic acid
• D-P-HYDROXYPHENYLGLYCINE
• (R)-alpha-Amino-4-hydroxybenzeneacetic acid
• 4-Hydroxyphenylglycine, D-(-)-
• p-hydroxy-D-phenylglycine
• PCM9OIX717
• (2R)-amino(4-hydroxyphenyl)acetic acid
• P-hydroxy-(R)-phenylglycine
• (R)-2-(4-HYDROXYPHENYL)GLYCINE
• D-(-)-p-Hydroxyphenylglycine
• CHEBI:15695
• (R)-(4-HYDROXYPHENYL)GLYCINE
• D-(-)-amino(4-hydroxyphenyl)acetic acid
• (2R)-amino(4-hydroxyphenyl)ethanoic acid
• D-2-amino-2-(p-hydroxyphenyl)acetic acid
• D-(-)-2-(P-HYDROXYPHENYL)GLYCINE
• (R)-Ethyl 2-amino-2-(4-hydroxyphenyl)acetate
• MFCD00004262
• UNII-PCM9OIX717
• Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.R)-
• Benzeneacetic acid, a-amino-4-hydroxy-, (aR)-
• EINECS 245-247-7
• Cefprozil impurity A
• (alphaR)-alpha-Amino-4-hydroxybenzeneacetic acid
• 4-HYDROXY-D-(-)-2-PHENYLGLYCINE
• d-4-hydroxyphenylglicyne
• Cefprozil EP Impurity A
• Epitope ID:117718
• EC 245-247-7
• SCHEMBL124861
• D-?-(4-hydroxyphenyl)glycine
• Benzeneacetic acid, alpha-amino-4-hydroxy-, (alphaR)-
• D-alpha-(4-hydroxyphenyl)glycine
• LJCWONGJFPCTTL-SSDOTTSWSA-N
• DTXSID401014840
• (R)-(4-Hydroxyphenyl)glycine; (R)-2-(4-Hydroxyphenyl)glycine; 4-Hydroxy-D-phenylglycine; D-(-)-2-(4-Hydroxyphenyl)glycine; D-(-)-2-(p-Hydroxyphenyl)glycine
• 4-Hydroxy-D-phenylglycine, >=98%
• D-(-)-2-(4-Hydroxyphenyl)glycine
• AKOS006281607
• AKOS015924172
• AC-1085
• DB04308
• (R)--Amino-4-hydroxybenzeneacetic acid
• D-.ALPHA.-P-HYDROXYPHENYLGLYCINE
• NCGC00164509-02
• AS-12542
• HY-34588
• CEFPROZIL IMPURITY A [EP IMPURITY]
• CEFADROXIL IMPURITY A [EP IMPURITY]
• AMOXICILLIN IMPURITY I [EP IMPURITY]
• CS-0020117
• GLYCINE, 2-(P-HYDROXYPHENYL)-, D-
• H0758
• C03493
• D71081
• EN300-105272
• D-(-)-.ALPHA.-(4-HYDROXYPHENYL)GLYCINE
• A816374
• D-.ALPHA.-AMINO-4-HYDROXYPHENYLACETIC ACID
• AMOXICILLIN TRIHYDRATE IMPURITY I [EP IMPURITY]
• CEFADROXIL MONOHYDRATE IMPURITY A [EP IMPURITY]
• CEFPROZIL MONOHYDRATE IMPURITY A [EP IMPURITY]
• Q27095129
• D-(-)-.ALPHA.-AMINO-4-HYDROXYPHENYLACETIC ACID
• Z1198149764
• (R)-(-)-2-AMINO-2-(4-HYDROXYPHENYL)ACETIC ACID
• (.ALPHA.R)-.ALPHA.-AMINO-4-HYDROXYBENZENEACETIC ACID
• Cefprozil impurity A, European Pharmacopoeia (EP) Reference Standard
• (2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetate;(R)-2-Amino-2-(4-hydroxyphenyl)acetic Acid
• D-alpha-(4-Hydroxy-phenyl)glycine, European Pharmacopoeia (EP) Reference Standard
• Amoxicillin EP Impurity I; (2R)-2-Amino-2-(4-hydroxyphenyl)acetic acid; (R)-(4-Hydroxyphenyl)glycine; (R)-Ethyl 2-Amino-2-(4-hydroxyphenyl)acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.6958	69.58%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6110	61.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9427	94.27%
OATP1B3 inhibitior	+	0.9628	96.28%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9427	94.27%
P-glycoprotein inhibitior	-	0.9886	98.86%
P-glycoprotein substrate	-	0.9547	95.47%
CYP3A4 substrate	-	0.7995	79.95%
CYP2C9 substrate	-	0.8101	81.01%
CYP2D6 substrate	-	0.7601	76.01%
CYP3A4 inhibition	-	0.8779	87.79%
CYP2C9 inhibition	-	0.9803	98.03%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9865	98.65%
CYP1A2 inhibition	-	0.9129	91.29%
CYP2C8 inhibition	-	0.9388	93.88%
CYP inhibitory promiscuity	-	0.9817	98.17%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.5694	56.94%
Carcinogenicity (trinary)	Non-required	0.6472	64.72%
Eye corrosion	-	0.9962	99.62%
Eye irritation	+	0.9825	98.25%
Skin irritation	-	0.6951	69.51%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9078	90.78%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.5507	55.07%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7071	70.71%
Acute Oral Toxicity (c)	III	0.4728	47.28%
Estrogen receptor binding	-	0.9096	90.96%
Androgen receptor binding	+	0.6218	62.18%
Thyroid receptor binding	-	0.6682	66.82%
Glucocorticoid receptor binding	-	0.8851	88.51%
Aromatase binding	-	0.8665	86.65%
PPAR gamma	+	0.5555	55.55%
Honey bee toxicity	-	0.9399	93.99%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	-	0.5106	51.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	94.37%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.13%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.29%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.23%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.85%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.27%	94.08%
CHEMBL2581	P07339	Cathepsin D	83.26%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.33%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.13%	99.15%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 89853
• LOTUS: LTS0172620
• wikiData: Q27095129