Identification

Generic Name
(S)-Mandelic acid
DrugBank Accession Number
DB03357
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 152.1473
Monoisotopic: 152.047344122
Chemical Formula
C8H8O3
Synonyms
  • (S)-2-Hydroxy-2-phenylacetic acid
  • (S)-Mandelsäure
  • (S)-α-hydroxybenzeneacetic acid
  • L-mandelic acid

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMandelate racemaseNot AvailablePseudomonas 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
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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:32800)
Affected organisms
Not Available

Chemical Identifiers

UNII
L0UMW58G3T
CAS number
17199-29-0
InChI Key
IWYDHOAUDWTVEP-ZETCQYMHSA-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-/m0/s1
IUPAC Name
(2S)-2-hydroxy-2-phenylacetic acid
SMILES
O[C@H](C(O)=O)C1=CC=CC=C1

References

General References
Not Available
Human Metabolome Database
HMDB0000703
KEGG Compound
C01984
PubChem Compound
439616
PubChem Substance
46507928
ChemSpider
388690
BindingDB
16420
ChEBI
32800
ChEMBL
CHEMBL58910
ZINC
ZINC000000000036
PDBe Ligand
SMN
PDB Entries
1mdl / 3tte / 4p56 / 5zzr / 6a0v

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)119 °CPhysProp
water solubility1.81E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.62HANSCH,C ET AL. (1995)
pKa3.41 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP0.66ALOGPS
logP0.9ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m3·mol-1ChemAxon
Polarizability14.66 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004j-0900000000-b53183d87b331db9b7db
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-0zfr-0900000000-31443907299c1634fe9f
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0pdi-4900000000-d32dc8f06b5e94c7b3b9
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0zfr-1900000000-f1e179f7f6654c244250
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-0900000000-15fb1f5429449730eb57
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a4i-1900000000-66724d8d0612c1da0f0a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4l-9500000000-6d480b6841c2a90ea872
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4l-9100000000-817dbc1408c9336f23cc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9000000000-f924dd96a6635e2ad5b2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0900000000-15fb1f5429449730eb57
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-1900000000-66724d8d0612c1da0f0a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9500000000-96b7d7c57c085b66c0aa
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9100000000-817dbc1408c9336f23cc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-f924dd96a6635e2ad5b2
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

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Details
1. Mandelate 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52