Showing metabocard for Threonic acid (MMDBc0000380)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:36:30 UTC
Update Date2024-04-30 19:32:01 UTC
Metabolite IDMMDBc0000380
Metabolite Identification
Common NameThreonic acid
DescriptionThreonic acid, also known as threonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID:21034532 ). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component in aqueous humour and blood (PMID:10420182 ). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID:20615997 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2d59da020>


  Mrv1652303062020122D          

  9  8  0  0  0  0            999 V2000
 9992.1939 9992.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.9079 9992.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.6226 9992.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3375 9992.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9079 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9992.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7628 9992.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1939 9991.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fe2d59da020>

HMDB0000943
     RDKit          3D
Threonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.9325   -1.6479   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -0.4834   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    0.5915   -1.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.2673    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4008   -1.4650    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    0.5546    0.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0575    1.7408   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -0.1252   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -1.3156   -0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.1157   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.3418    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -1.3592    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    0.8121    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    2.5369    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613   -0.3643   -1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.5487   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -1.2142    0.5244 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:0x00007fe2d59da020>


  Mrv1652303062020122D          

  9  8  0  0  0  0            999 V2000
 9992.1939 9992.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.9079 9992.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.6226 9992.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3375 9992.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9079 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9992.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7628 9992.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1939 9991.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000380

> <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+/m0/s1

> <INCHI_KEY>
JPIJQSOTBSSVTP-STHAYSLISA-N

> <FORMULA>
C4H8O5

> <MOLECULAR_WEIGHT>
136.1033

> <EXACT_MASS>
136.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.609117870375558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-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>
3.4007287139451505

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981778620620938

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
26.345999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
threonate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe2d59da020>

HMDB0000943
     RDKit          3D
Threonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.9325   -1.6479   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -0.4834   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    0.5915   -1.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.2673    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4008   -1.4650    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    0.5546    0.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0575    1.7408   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -0.1252   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -1.3156   -0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.1157   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.3418    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -1.3592    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    0.8121    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    2.5369    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613   -0.3643   -1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.5487   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -1.2142    0.5244 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:0x00007fe2d59da020>

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8652.0958652.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.4288653.098   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8654.7628652.329   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8656.0978653.098   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8653.4288654.638   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8650.7608653.098   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8649.4248652.329   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8650.7608654.638   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8652.0958650.789   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for #<Metabolite:0x00007fe2d59da020>

COMPND    HMDB0000943
HETATM    1  O1  UNL     1       1.932  -1.648  -0.906  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.593  -0.483  -0.572  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.035   0.591  -1.322  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.737  -0.267   0.600  1.00  0.00           C  
HETATM    5  O3  UNL     1       0.401  -1.465   1.217  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.494   0.555   0.289  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.058   1.741  -0.331  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.424  -0.125  -0.662  1.00  0.00           C  
HETATM    9  O5  UNL     1      -1.934  -1.316  -0.178  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.877   1.116  -1.103  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.336   0.342   1.335  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.061  -1.359   2.123  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.021   0.812   1.230  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.311   2.537   0.220  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.861  -0.364  -1.588  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.263   0.549  -0.873  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.607  -1.214   0.524  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:0x00007fe2d59da020>

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

INCHI for #<Metabolite:0x00007fe2d59da020>

InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1
Download
Synonyms
ValueSource
L-ThreonateKegg
(2R,3S)-2,3,4-Trihydroxybutanoic acidKegg
L-Threonic acidGenerator
(2R,3S)-2,3,4-TrihydroxybutanoateGenerator
ThreonateGenerator
Threonic acid, (R-(r*,s*))-isomerHMDB
2,3,4-Trihydroxy-(threo)-butanoic acidHMDB
Threonic acid, (r*,r*)-isomerHMDB
2,3,4-Trihydroxybutanoic acidHMDB
2,3,4-Trihydroxybutyric acidHMDB
Threonic acidMeSH, HMDB
Molecular FormulaC4H8O5
Average Mass136.1033
Monoisotopic Mass136.037173366
IUPAC Name(2R,3S)-2,3,4-trihydroxybutanoic acid
Traditional Namethreonate
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+/m0/s1
InChI KeyJPIJQSOTBSSVTP-STHAYSLISA-N