Glycolic acid

Identification

Name
Glycolic acid
Accession Number
DB03085  (EXPT01629, DB11307)
Type
Small Molecule
Groups
Approved, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • 2-Hydroxyacetic acid
  • 2-Hydroxyethanoic acid
  • alpha-Hydroxyacetic acid
  • Glycollic acid
  • Hydroxyacetic Acid
  • Hydroxyethanoic Acid
  • α-hydroxyacetic acid
External IDs
NSC-166
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
bdr Re-action deep low base skin refiner exfoliation essenceLiquid3 g/30mLTopicalHanaim International Llc2016-11-14Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AHA 7 Whitehead Power LiquidGlycolic acid (7 mg/100mL) + Nicotinamide (2 mg/100mL)LiquidTopicalCosrx Inc.2015-12-232017-06-29Us
Clear Cell Salicylic Clarifying TonicGlycolic acid (50 mg/mL) + Salicylic acid (30 mg/mL)LiquidTopicalAllure Labs, Inc.2010-01-01Not applicableUs
Categories
UNII
0WT12SX38S
CAS number
79-14-1
Weight
Average: 76.0514
Monoisotopic: 76.016043994
Chemical Formula
C2H4O3
InChI Key
AEMRFAOFKBGASW-UHFFFAOYSA-N
InChI
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
IUPAC Name
2-hydroxyacetic acid
SMILES
OCC(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlucose-6-phosphate 1-dehydrogenaseNot AvailableHuman
UGlycine oxidaseNot AvailableBacillus subtilis (strain 168)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

David Y. Tang, Arthur M. Foster, "(3-Trifluoromethylphenyl)-alpha-hydroxyacetic acid and process for preparation." U.S. Patent US4296244, issued January, 1977.

US4296244
General References
Not Available
External Links
Human Metabolome Database
HMDB00115
KEGG Compound
C03547
PubChem Compound
757
PubChem Substance
46508186
ChemSpider
737
ChEBI
17497
ChEMBL
CHEMBL252557
HET
GOA
PDB Entries
1qki / 1ryi / 2h8p / 2hfe / 2hg5 / 2o99 / 3if9 / 3l24 / 3nyg / 3r3z
show 18 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentAcne Scars1
2Unknown StatusTreatmentSolar Elastosis1
4Not Yet RecruitingTreatmentMelasma1
Not AvailableCompletedTreatmentFlat Warts (Diagnosis) / Human Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical3 g/30mL
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)79.5 °CPhysProp
logP-1.11HANSCH,C ET AL. (1995)
pKa3.83SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility608.0 mg/mLALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS0.9ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.35 m3·mol-1ChemAxon
Polarizability6.2 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.893
Blood Brain Barrier+0.651
Caco-2 permeable-0.7739
P-glycoprotein substrateNon-substrate0.7721
P-glycoprotein inhibitor INon-inhibitor0.976
P-glycoprotein inhibitor IINon-inhibitor0.9877
Renal organic cation transporterNon-inhibitor0.9549
CYP450 2C9 substrateNon-substrate0.8584
CYP450 2D6 substrateNon-substrate0.9123
CYP450 3A4 substrateNon-substrate0.8096
CYP450 1A2 substrateNon-inhibitor0.9308
CYP450 2C9 inhibitorNon-inhibitor0.9635
CYP450 2D6 inhibitorNon-inhibitor0.9736
CYP450 2C19 inhibitorNon-inhibitor0.9756
CYP450 3A4 inhibitorNon-inhibitor0.9693
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.989
Ames testNon AMES toxic0.9556
CarcinogenicityNon-carcinogens0.6589
BiodegradationReady biodegradable0.9398
Rat acute toxicity1.5594 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9917
hERG inhibition (predictor II)Non-inhibitor0.9585
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 - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0900000000-ed8b8e4a9e2556ea02e2
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dj-9600000000-8bafc88c7bf4e90fb5e8
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-003r-2910000000-bd50bf5bab6f5327eaf4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-cadf899be6b15d008330
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-e66ed28d8419895e0fb4
GC-MS Spectrum - EI-BGC-MSsplash10-0002-0900000000-7f84fac3284d17fa3ba6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-ed8b8e4a9e2556ea02e2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dj-9600000000-8bafc88c7bf4e90fb5e8
GC-MS Spectrum - GC-MSGC-MSsplash10-003r-2910000000-bd50bf5bab6f5327eaf4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-d724c85a3b30e3c2e4bc
Mass Spectrum (Electron Ionization)MSsplash10-001i-9000000000-2885890e3bb8c015742f
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-004i-9000000000-e942bdae1d60e5f5d649
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-00di-9000000000-f225de2de3540c3f50a4
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-00di-9000000000-7de217d97b44f53aad82
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-00di-9000000000-88af2b259f82cd1d8938
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-9000000000-c968a24f0640b154325b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0059-9000000000-1dfacf30bf94ce3bf8bb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-d961c3c14ec415e3141e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9000000000-67f73be970ba9f885c4a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-7445713a5fe347bbc8b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-26e13242443efc1aa846
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-6ba976b949118cd0a86a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-88af2b259f82cd1d8938
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9000000000-c968a24f0640b154325b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0059-9000000000-1dfacf30bf94ce3bf8bb
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Alpha hydroxy acids and derivatives
Direct Parent
Alpha hydroxy acids and derivatives
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alpha-hydroxy acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
primary alcohol, 2-hydroxy monocarboxylic acid (CHEBI:17497)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis. The main function of this enzyme is ...
Gene Name
G6PD
Uniprot ID
P11413
Uniprot Name
Glucose-6-phosphate 1-dehydrogenase
Molecular Weight
59256.31 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Glycine oxidase activity
Specific Function
Catalyzes the FAD-dependent oxidative deamination of various amines and D-amino acids to yield the corresponding alpha-keto acids, ammonia/amine, and hydrogen peroxide. Oxidizes sarcosine (N-methyl...
Gene Name
thiO
Uniprot ID
O31616
Uniprot Name
Glycine oxidase
Molecular Weight
40936.53 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:23