Showing metabocard for Glycolic acid (MMDBc0000030)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:27:49 UTC
Update Date2022-08-30 23:10:54 UTC
Metabolite IDMMDBc0000030
Metabolite Identification
Common NameGlycolic acid
DescriptionGlycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colourless, odourless, and hygroscopic crystalline solid is highly soluble in water. Due to its excellent capability to penetrate skin, glycolic acid is often used in skin care products, most often as a chemical peel. It may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. This allows the outer skin to dissolve, revealing the underlying skin. It is thought that this is due to the reduction of calcium ion concentrations in the epidermis and the removal of calcium ions from cell adhesions, leading to desquamation. Glycolic acid is a known inhibitor of tyrosinase. This can suppress melanin formation and lead to a lightening of skin colour. Acute doses of glycolic acid on skin or eyes leads to local effects that are typical of a strong acid (e.g. dermal and eye irritation). Glycolate is a nephrotoxin if consumed orally. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. Glycolic acid's renal toxicity is due to its metabolism to oxalic acid. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Renal tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic acid. Glycolic acid does exhibit some inhalation toxicity and can cause respiratory, thymus, and liver damage if present in very high levels over long periods of time. Elevated glycolic acid without elevated oxalic acid is most likely a result of GI yeast overgrowth (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). (http://drweyrich.weyrich.com/labs/oat.html). Glycolic acid has also been found to be a metabolite in Acetobacter, Acidithiobacillus, Alcaligenes, Corynebacterium, Cryptococcus, Escherichia, Gluconobacter, Kluyveromyces, Leptospirillum, Pichia, Rhodococcus, Rhodotorula and Saccharomyces (PMID: 11758919 ; PMID: 26360870 ; PMID: 14390024 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055d24b1e1c70>


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
10000.894810001.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.609610000.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.325910001.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.179410000.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.894810001.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055d24b1e1c70>

HMDB0000115
     RDKit          3D
Glycolic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
    0.5818    1.6591    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    0.5883    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    0.0447   -0.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.1396    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.2911   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105    0.2603   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    0.5210   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694   -0.3392    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.3035   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  3  6  1  0
  4  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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3D SDF for #<Metabolite:0x000055d24b1e1c70>


  Mrv1652309032023522D          

  5  4  0  0  0  0            999 V2000
10000.894810001.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.609610000.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.325910001.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.179410000.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.894810001.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000030

> <DATABASE_NAME>
MIME

> <SMILES>
OCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)

> <INCHI_KEY>
AEMRFAOFKBGASW-UHFFFAOYSA-N

> <FORMULA>
C2H4O3

> <MOLECULAR_WEIGHT>
76.0514

> <EXACT_MASS>
76.016043994

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
6.195837007972227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyacetic acid

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-1.0405937603333335

> <ALOGPS_LOGS>
0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.780077957574235

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.526322592592504

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6133096708862027

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
14.345899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.08e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycolic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000055d24b1e1c70>

HMDB0000115
     RDKit          3D
Glycolic acid
  9  8  0  0  0  0  0  0  0  0999 V2000
    0.5818    1.6591    0.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3893    0.5883    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180    0.0447   -0.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -0.1396    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214   -1.2911   -0.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105    0.2603   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    0.5210   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9694   -0.3392    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.3035   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  3  6  1  0
  4  7  1  0
  4  8  1  0
  5  9  1  0
M  END
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PDB for #<Metabolite:0x000055d24b1e1c70>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.3378668.618   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.6718667.849   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8671.0088668.618   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.0028667.849   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8668.3378670.161   0.000  0.00  0.00           O+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for #<Metabolite:0x000055d24b1e1c70>

COMPND    HMDB0000115
HETATM    1  O1  UNL     1       0.582   1.659   0.783  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.389   0.588   0.167  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.318   0.045  -0.695  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.882  -0.140   0.358  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.921  -1.291  -0.393  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.311   0.260  -0.683  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.697   0.521  -0.002  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.969  -0.339   1.455  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.130  -1.304  -0.989  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    6
CONECT    4    5    7    8
CONECT    5    9
END
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SMILES for #<Metabolite:0x000055d24b1e1c70>

OCC(O)=O
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INCHI for #<Metabolite:0x000055d24b1e1c70>

InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
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Synonyms
ValueSource
2-Hydroxyacetic acidChEBI
2-Hydroxyethanoic acidChEBI
alpha-Hydroxyacetic acidChEBI
Glycollic acidChEBI
HOCH2COOHChEBI
Hydroxyacetic acidChEBI
Hydroxyethanoic acidChEBI
2-HydroxyacetateGenerator
2-HydroxyethanoateGenerator
a-HydroxyacetateGenerator
a-Hydroxyacetic acidGenerator
alpha-HydroxyacetateGenerator
Α-hydroxyacetateGenerator
Α-hydroxyacetic acidGenerator
GlycollateGenerator
HydroxyacetateGenerator
HydroxyethanoateGenerator
GlycolateGenerator
GlycocideHMDB
GlyPureHMDB
GlyPure 70HMDB
Sodium glycolateHMDB
Glycolic acid, 2-(14)C-labeledHMDB
Glycolic acid, 1-(14)C-labeledHMDB
Glycolic acid, potassium saltHMDB
Glycolic acid, monopotassium saltHMDB
Glycolic acid, calcium saltHMDB
Glycolic acid, monoammonium saltHMDB
Glycolic acid, monolithium saltHMDB
Glycolic acid, monosodium saltHMDB
Potassium glycolateHMDB
Molecular FormulaC2H4O3
Average Mass76.0514
Monoisotopic Mass76.016043994
IUPAC Name2-hydroxyacetic acid
Traditional Nameglycolic acid
CAS Registry Number79-14-1
SMILES
OCC(O)=O
InChI Identifier
InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
InChI KeyAEMRFAOFKBGASW-UHFFFAOYSA-N