Showing metabocard for Erythronic acid (MMDBc0000357)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:02 UTC
Update Date2024-04-30 19:31:55 UTC
Metabolite IDMMDBc0000357
Metabolite Identification
Common NameErythronic acid
DescriptionErythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF, and synovial fluid (PMID: 14708889 , 8087979 , 8376520 , 10420182 ). Erythronic acid is formed when N-acetyl-D-glucosamine (GlcNAc) is oxidized. GlcNAc is a constituent of hyaluronic acid (HA), a polysaccharide consisting of alternating units of glucuronic acid and GlcNAc, present as an aqueous solution in synovial fluid. In the synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase (PMID: 10614067 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9a2e0d0>

Erythronic acid.mol
  Mrv1652305231918522D          

  9  8  0  0  0  0            999 V2000
   -0.2063    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0311    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -0.7144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0312   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312    0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005645c9a2e0d0>

HMDB0000613
     RDKit          3D
Erythronic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.6206    2.1035   -0.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982    1.1192   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    1.0639   -0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6823    0.0611    0.7743 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6470   -0.9238    1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -0.6379    0.1045 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1297   -1.2876   -1.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    0.2878   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626   -0.4081   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957    0.9467    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    0.5035    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -1.1744    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.4302    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516   -2.2729   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    1.0695   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203    0.7724    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107    0.2075   -0.9506 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  1
  5 12  1  0
  6 13  1  1
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005645c9a2e0d0>

Erythronic acid.mol
  Mrv1652305231918522D          

  9  8  0  0  0  0            999 V2000
   -0.2063    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0311    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -0.7144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0312   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312    0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000357

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@@H](O)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3-/m1/s1

> <INCHI_KEY>
JPIJQSOTBSSVTP-PWNYCUMCSA-N

> <FORMULA>
C4H8O5

> <MOLECULAR_WEIGHT>
136.1033

> <EXACT_MASS>
136.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.68417031731118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2,3,4-trihydroxybutanoic acid

> <ALOGPS_LOGP>
-2.11

> <JCHEM_LOGP>
-2.149074426666667

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.025178139889814

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4007287139451523

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981778620620938

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
26.346

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythronic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00005645c9a2e0d0>

HMDB0000613
     RDKit          3D
Erythronic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.6206    2.1035   -0.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2982    1.1192   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    1.0639   -0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6823    0.0611    0.7743 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6470   -0.9238    1.0747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -0.6379    0.1045 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1297   -1.2876   -1.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    0.2878   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626   -0.4081   -0.5511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3957    0.9467    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018    0.5035    1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389   -1.1744    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.4302    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516   -2.2729   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    1.0695   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203    0.7724    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4107    0.2075   -0.9506 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  1
  5 12  1  0
  6 13  1  1
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

PDB for #<Metabolite:0x00005645c9a2e0d0>

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Erythronic acid.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.385   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.385   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.925   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.385  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.925  -1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.385  -2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.925  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.925   1.334   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.385   2.667   0.000  0.00  0.00           O+0
CONECT    1    2    8    9                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for #<Metabolite:0x00005645c9a2e0d0>

COMPND    HMDB0000613
HETATM    1  O1  UNL     1       0.621   2.104  -0.401  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.298   1.119  -0.020  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.630   1.064  -0.369  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.682   0.061   0.774  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.647  -0.924   1.075  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.462  -0.638   0.105  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.130  -1.288  -1.062  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.643   0.288  -0.120  1.00  0.00           C  
HETATM    9  O5  UNL     1      -2.763  -0.408  -0.551  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.396   0.947   0.282  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.302   0.504   1.712  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.139  -1.174   0.260  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.812  -1.430   0.828  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.152  -2.273  -0.976  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.424   1.069  -0.858  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.920   0.772   0.846  1.00  0.00           H  
HETATM   17  H8  UNL     1      -3.411   0.208  -0.951  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    6   11
CONECT    5   12
CONECT    6    7    8   13
CONECT    7   14
CONECT    8    9   15   16
CONECT    9   17
END
Download

SMILES for #<Metabolite:0x00005645c9a2e0d0>

OC[C@@H](O)[C@@H](O)C(O)=O
Download

INCHI for #<Metabolite:0x00005645c9a2e0d0>

InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3-/m1/s1
Download
Synonyms
ValueSource
Erythro-2,3,4-trihydroxybutyric acidChEBI
Erythro-2,3,4-trihydroxybutyrateGenerator
ErythronateGenerator
(R*,r*)-2,3,4-trihydroxy-butanoateHMDB
(R*,r*)-2,3,4-trihydroxy-butanoic acidHMDB
2,3,4-TrihydroxybutanoateHMDB
2,3,4-Trihydroxybutanoic acidHMDB
D-ErythronateHMDB
Erythronic acidChEBI
Molecular FormulaC4H8O5
Average Mass136.1033
Monoisotopic Mass136.037173366
IUPAC Name(2R,3R)-2,3,4-trihydroxybutanoic acid
Traditional Nameerythronic acid
CAS Registry NumberNot Available
SMILES
OC[C@@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3-/m1/s1
InChI KeyJPIJQSOTBSSVTP-PWNYCUMCSA-N