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Record Information
Version1.0
Created at2020-11-23 19:41:19 UTC
Updated at2021-08-12 19:52:15 UTC
NP-MRD IDNP0002823
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-4-hydroxyphenylglycine
Provided ByBMRBBMRB logo
Description It was first documented in 2002 (PMID: 11932455). Based on a literature review a significant number of articles have been published on Oxfenicine (PMID: 17984079) (PMID: 34380192) (PMID: 34380191) (PMID: 34380190).
Structure
Thumb
Synonyms
ValueSource
(2S)-Amino(4-hydroxyphenyl)ethanoic acidChEBI
(2S)-Amino(4-hydroxyphenyl)ethanoateGenerator
4-Hydroxyphenylglycine, (+-)-isomerMeSH
4-Hydroxyphenylglycine, monosodium saltMeSH
4-Hydroxyphenylglycine, (R)-isomerMeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomerMeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomerMeSH
(R,S)-3HPGMeSH
4-HydroxyphenylglycineMeSH
4-Hydroxyphenylglycine hydrobromide, (+-)-isomerMeSH
4-Hydroxyphenylglycine hydrochloride, (R)-isomerMeSH
D-P-HydroxyphenylglycineMeSH
P-HydroxyphenylglycineMeSH
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
OxfenicineMeSH
Chemical FormulaC8H9NO3
Average Mass167.1620 Da
Monoisotopic Mass167.05824 Da
IUPAC Name(2S)-2-amino-2-(4-hydroxyphenyl)acetic acid
Traditional Nameoxfenicine
CAS Registry NumberNot Available
SMILES
N[C@H](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-/m0/s1
InChI KeyLJCWONGJFPCTTL-ZETCQYMHSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
Polarizability16.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04291
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID33241
KEGG Compound IDC12323
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID31755
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Recktenwald J, Shawky R, Puk O, Pfennig F, Keller U, Wohlleben W, Pelzer S: Nonribosomal biosynthesis of vancomycin-type antibiotics: a heptapeptide backbone and eight peptide synthetase modules. Microbiology (Reading). 2002 Apr;148(Pt 4):1105-1118. doi: 10.1099/00221287-148-4-1105. [PubMed:11932455 ]
  3. Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
  4. Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
  5. Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]