(R)-Mandelic acid
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Identification
- Generic Name
- (R)-Mandelic acid
- DrugBank Accession Number
- DB02280
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 152.1473
Monoisotopic: 152.047344122 - Chemical Formula
- C8H8O3
- Synonyms
- (−)-(R)-mandelic acid
- (−)-mandelic acid
- (−)-α-hydroxyphenylacetic acid
- (2R)-2-hydroxy-2-phenylacetic acid
- (R)-2-Hydroxy-2-phenylacetic acid
- (R)-Mandelsäure
- (R)-α-hydroxybenzeneacetic acid
- (R)-α-hydroxyphenylacetic acid
- D-2-phenylglycolic acid
- D-mandelic acid
- D(−)-mandelic acid
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UBenzoylformate decarboxylase Not Available Pseudomonas putida UMandelate racemase Not Available Pseudomonas putida - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Not Available
- Direct Parent
- Benzene and substituted derivatives
- Alternative Parents
- Alpha hydroxy acids and derivatives / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Aromatic alcohols
- Substituents
- Alcohol / Alpha-hydroxy acid / Aromatic alcohol / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxy acid / Monocarboxylic acid or derivatives
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- mandelic acid (CHEBI:17656)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- PPL7YW1M9W
- CAS number
- 611-71-2
- InChI Key
- IWYDHOAUDWTVEP-SSDOTTSWSA-N
- InChI
- InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
- IUPAC Name
- (2R)-2-hydroxy-2-phenylacetic acid
- SMILES
- O[C@@H](C(O)=O)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0062635
- KEGG Compound
- C01983
- PubChem Compound
- 11914
- PubChem Substance
- 46506374
- ChemSpider
- 11420
- BindingDB
- 16421
- ChEBI
- 17656
- ChEMBL
- CHEMBL292411
- ZINC
- ZINC000000164392
- PDBe Ligand
- RMN
- PDB Entries
- 1mcz / 1mdl / 3zgj / 4p56 / 5zzx
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 119 °C PhysProp water solubility 1.1E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 16.8 mg/mL ALOGPS logP 0.66 ALOGPS logP 0.9 Chemaxon logS -0.96 ALOGPS pKa (Strongest Acidic) 3.75 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 38.7 m3·mol-1 Chemaxon Polarizability 14.66 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9629 Blood Brain Barrier + 0.6604 Caco-2 permeable + 0.6084 P-glycoprotein substrate Non-substrate 0.7248 P-glycoprotein inhibitor I Non-inhibitor 0.9835 P-glycoprotein inhibitor II Non-inhibitor 0.9896 Renal organic cation transporter Non-inhibitor 0.9327 CYP450 2C9 substrate Non-substrate 0.8496 CYP450 2D6 substrate Non-substrate 0.949 CYP450 3A4 substrate Non-substrate 0.8024 CYP450 1A2 substrate Non-inhibitor 0.9456 CYP450 2C9 inhibitor Non-inhibitor 0.8957 CYP450 2D6 inhibitor Non-inhibitor 0.973 CYP450 2C19 inhibitor Non-inhibitor 0.9812 CYP450 3A4 inhibitor Non-inhibitor 0.9729 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9714 Ames test Non AMES toxic 0.9532 Carcinogenicity Non-carcinogens 0.7492 Biodegradation Ready biodegradable 0.8431 Rat acute toxicity 1.5508 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9888 hERG inhibition (predictor II) Non-inhibitor 0.9627
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets

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1. DetailsBenzoylformate decarboxylase
- Kind
- Protein
- Organism
- Pseudomonas putida
- Pharmacological action
- Unknown
- General Function
- Thiamine pyrophosphate binding
- Specific Function
- Not Available
- Gene Name
- mdlC
- Uniprot ID
- P20906
- Uniprot Name
- Benzoylformate decarboxylase
- Molecular Weight
- 56354.475 Da
References
2. DetailsMandelate racemase
- Kind
- Protein
- Organism
- Pseudomonas putida
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Not Available
- Gene Name
- mdlA
- Uniprot ID
- P11444
- Uniprot Name
- Mandelate racemase
- Molecular Weight
- 38564.39 Da
References
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14