(S)-3,5-Dihydroxyphenylglycine
Basic information
- CAS
162870-29-3- Standard SMILES
N[C@H](C(=O)O)c1cc(O)cc(O)c1- InChIKey
HOOWCUZPEFNHDT-ZETCQYMHSA-N- Molecular formula
- C8H9NO4
- Average molar mass
- 183.16 g/mol
- Monoisotopic mass
- 183.05315777
Overview
(S)-3,5-dihydroxyphenylglycine is a glycine derivative that is L-alpha-phenylglycine substituted at positions 3 and 5 on the phenyl ring by hydroxy groups. It is a member of resorcinols and a non-proteinogenic L-alpha-amino acid. It is functionally related to a L-alpha-phenylglycine. It is a tautomer of a (S)-3,5-dihydroxyphenylglycine zwitterion.
Names & identifiers
- Preferred name
- (S)-3,5-Dihydroxyphenylglycine
- IUPAC
- (2S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid
- English name
- (S)-3,5-Dihydroxyphenylglycine
- Molecular formula
- C8H9NO4
- Molecular weight
- 183.16
Names & synonyms
(S)-3,5-Dihydroxyphenylglycine162870-29-3L-3,5-DihydroxyphenylglycineS-DHPGDihydroxyphenylglycine(2S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid3,5-Dihydroxy-L-phenylglycineJ516.528HCF5G2G268ABenzeneacetic acid, alpha-amino-3,5-dihydroxy-, (alphaS)-CHEBI:29474DTXSID20904031
Show more names
(S) 3,5 DHPG,(S)3,5DHPG(S)-3,5-Dihydroxylphenylglycine(S)-3,5-DHPG, group I mGlu agonist(S)-3,5-DHPG (mM/ml), group I mGlu agonist
RefChem:906453DTXCID601331953(S)-3,5-DHPG(S)-3,5-Dihydroxyphenylglycine hydrate(S)-3,5 DHPG(S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acidCHEMBL39221HMS3411L21
Database identifiers
- CAS
162870-29-3- PubChem CID
- 443586
- DTXSID
DTXSID20904031- ChEMBL
CHEMBL39221- ChEBI
CHEBI:29474- UNII
- CF5G2G268A
- Nikkaji
- J516.528H
Properties
Computed structural properties
- XLogP
- -2.4
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 187
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 207 °C · >207°C (dec.)
- Boiling point
- 448.8 · 448.8±33.0 °C(Predicted)
- Density
- 1.55 · 1.550±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- Aqueous Base (Very Slightly, Sonicated), Methanol (Slightly), Water (Slightly, Heated)
- form
- solid
- pka
- 1.77 · 1.77±0.10(Predicted)
- color
- white
- Water Solubility
- 50 mM · Soluble to 50 mM in water
- Stability
- Hygroscopic
- InChI
- 1S/C8H9NO4.H2O/c9-7(8(12)13)4-1-5(10)3-6(11)2-4;/h1-3,7,10-11H,9H2,(H,12,13);1H2/t7-;/m0./s1
- InChIKey
- QZEFIWWBQUKNFA-FJXQXJEOSA-N
- SMILES
- O.N[C@H](C(O)=O)c1cc(O)cc(O)c1
- FDA UNII
- 5 G2G268A · CF5G2G268A
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses(S)-3,5-Dihydroxylphenylglycine is a potent agonist of group I metabotropic glutamate receptors mGluR1 and mGluR5. (S)-3,5-Dihydroxylphenylglycine have been utilized for the treatment of neuronal injury and cognitive enhancement.
Uses(S)-3,5-Dihydroxyphenylglycine hydrate has been used: as mGluR1/5agonist for metabotropic glutamate receptor 1 (mGluR1/5) activation in synaptoneurosomal preparations in ACSF for DHPG stimulation to inject into basolateral amygdala to study its effect on memory expression
Additional notes
DefinitionChEBI: (S)-3,5-dihydroxyphenylglycine is a glycine derivative that is L-alpha-phenylglycine substituted at positions 3 and 5 on the phenyl ring by hydroxy groups. It is a member of resorcinols and a non-proteinogenic L-alpha-amino acid. It is functionally related to a L-alpha-phenylglycine. It is a tautomer of a (S)-3,5-dihydroxyphenylglycine zwitterion.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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