NAV

(R)-Mandelic acid

Identification

Generic Name
(R)-Mandelic acid
DrugBank Accession Number
DB02280
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBenzoylformate decarboxylaseNot AvailablePseudomonas putida
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: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
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

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 solubility1.1E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
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
PropertyValueProbability
Human Intestinal Absorption+0.9629
Blood Brain Barrier+0.6604
Caco-2 permeable+0.6084
P-glycoprotein substrateNon-substrate0.7248
P-glycoprotein inhibitor INon-inhibitor0.9835
P-glycoprotein inhibitor IINon-inhibitor0.9896
Renal organic cation transporterNon-inhibitor0.9327
CYP450 2C9 substrateNon-substrate0.8496
CYP450 2D6 substrateNon-substrate0.949
CYP450 3A4 substrateNon-substrate0.8024
CYP450 1A2 substrateNon-inhibitor0.9456
CYP450 2C9 inhibitorNon-inhibitor0.8957
CYP450 2D6 inhibitorNon-inhibitor0.973
CYP450 2C19 inhibitorNon-inhibitor0.9812
CYP450 3A4 inhibitorNon-inhibitor0.9729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9714
Ames testNon AMES toxic0.9532
CarcinogenicityNon-carcinogens0.7492
BiodegradationReady biodegradable0.8431
Rat acute toxicity1.5508 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9888
hERG inhibition (predictor II)Non-inhibitor0.9627
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-004i-0900000000-da7c8450b1708d6b5b44
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004i-0900000000-bf406a068b57bcc07ca2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9600000000-0d67f110027658a584a4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0zfr-5900000000-45499f2c996208e0143f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9100000000-b577195913c64f43bc8f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-3030385b2c46c76f7d40
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-d57db09a0e7c73a976bc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-5a80a2a733ffb7d2962f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0900000000-26a5fcf7f098faa99c2d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3900000000-b5c253888613a4454a46
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-8dc8d32f2c1796485465
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-177b73f2507c01d2e77f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9300000000-0c5b79c43cffd766465c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-9000000000-7c96226fbe7b5cc4b6fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bvi-9600000000-cd0df63024d84cb04040
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.6199102
predicted
DarkChem Lite v0.1.0
[M-H]-132.5337102
predicted
DarkChem Lite v0.1.0
[M-H]-132.6191102
predicted
DarkChem Lite v0.1.0
[M-H]-130.39088
predicted
DeepCCS 1.0 (2019)
[M+H]+135.3494102
predicted
DarkChem Lite v0.1.0
[M+H]+133.7542102
predicted
DarkChem Lite v0.1.0
[M+H]+132.1651102
predicted
DarkChem Lite v0.1.0
[M+H]+132.78644
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.4869102
predicted
DarkChem Lite v0.1.0
[M+Na]+132.4325102
predicted
DarkChem Lite v0.1.0
[M+Na]+132.4823102
predicted
DarkChem Lite v0.1.0
[M+Na]+139.82231
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Benzoylformate 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
  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]
Details2. 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 July 02, 2020 13:14