Showing metabocard for Ascorbic acid (MMDBc0000013)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:24:46 UTC
Update Date2024-09-27 18:32:25 UTC
Metabolite IDMMDBc0000013
Metabolite Identification
Common NameAscorbic acid
DescriptionAscorbic acid is found naturally in citrus fruits and many vegetables and is an essential nutrient in human diets. It is necessary to maintain connective tissue and bone. The biologically active form of ascorbic acid is vitamin C. Vitamin C is a water soluble vitamin. Primates (including humans) and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid and must obtain it in their food. Vitamin C functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant (PubChem). Ascorbic acid is an electron donor for enzymes involved in collagen hydroxylation, biosynthesis of carnitine and norepinephrine, tyrosine metabolism, and amidation of peptide hormones. Ascrobic acid (vitamin C) deficiency causes scurvy. The amount of vitamin C necessary to prevent scurvy may not be adequate to maintain optimal health. The ability of vitamin C to donate electrons also makes it a potent water-soluble antioxidant that readily scavenges free radicals such as molecular oxygen, superoxide, hydroxyl radical, and hypochlorous acid. In this setting, several mechanisms could account for a link between vitamin C and heart disease. One is the relation between LDL oxidation and vitamins C and E. Vitamin C in vitro can recycle vitamin E, which can donate electrons to prevent LDL oxidation in vitro. As the lipid-phase vitamin E is oxidized, it can be regenerated by aqueous vitamin C. Other possibilities are that vitamin C could decrease cholesterol by mechanisms not well characterized, or could improve vasodilatation and vascular reactivity, perhaps by decreasing the interactions of nitric oxide with oxidants (PMID: 10799361 ). Moreover, ascorbic acid is found to be associated with hyperoxalemia, which is an inborn error of metabolism. Ascorbic acid is also a microbial metabolite produced by Ketogulonicigenium (PMID: 15785002 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f53b88aa8a0>

  Mrv1652309032023502D          

 13 13  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -1.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -1.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -0.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -0.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -0.0724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3819    0.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2508   -1.0683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
 12  1  1  0  0  0  0
  7  2  1  0  0  0  0
  6  3  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
 12  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 13  1  6  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f53b88aa8a0>

HMDB0000044
     RDKit          3D
Ascorbic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.1646   -2.2190   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5134   -1.3287   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -1.5369    0.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -0.3090    1.0144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4330   -0.0952    0.8450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8415    1.1479    1.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -0.3072   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -1.5322   -1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638    0.6994    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8100    2.0938    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    0.0983   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    0.7125   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -0.2098    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469   -0.8623    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    1.5011    1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199    0.4928   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9727   -0.2477   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -1.4828   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990    2.7050   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189    0.6799   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11  2  1  0
  4 13  1  1
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f53b88aa8a0>

  Mrv1652309032023502D          

 13 13  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -1.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -1.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -0.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -0.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -0.0724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3819    0.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2508   -1.0683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
 12  1  1  0  0  0  0
  7  2  1  0  0  0  0
  6  3  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
 12  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 13  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000013

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

> <INCHI_KEY>
CIWBSHSKHKDKBQ-JLAZNSOCSA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.932525092170716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-1.58

> <JCHEM_LOGP>
-1.9135588756666668

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.181873536050066

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.359916949362066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979728932431362

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
37.0321

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin C

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f53b88aa8a0>

HMDB0000044
     RDKit          3D
Ascorbic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.1646   -2.2190   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5134   -1.3287   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -1.5369    0.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491   -0.3090    1.0144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4330   -0.0952    0.8450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8415    1.1479    1.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713   -0.3072   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761   -1.5322   -1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638    0.6994    0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8100    2.0938    0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    0.0983   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    0.7125   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -0.2098    2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9469   -0.8623    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865    1.5011    1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199    0.4928   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9727   -0.2477   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554   -1.4828   -1.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990    2.7050   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189    0.6799   -0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11  2  1  0
  4 13  1  1
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
M  END
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PDB for #<Metabolite:0x00007f53b88aa8a0>

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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.675  -3.616   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.675  -3.616   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.711  -0.429   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.247  -0.135   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.913  -0.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.580  -0.135   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.580   1.405   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -2.335  -1.994   0.000  0.00  0.00           H+0
CONECT    1    4   12                                                       
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    3    4    7                                                  
CONECT    7    2    6   12                                                  
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12    1    7   10   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f53b88aa8a0>

COMPND    HMDB0000044
HETATM    1  O1  UNL     1       2.165  -2.219  -0.986  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.513  -1.329  -0.357  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.495  -1.537   0.557  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.049  -0.309   1.014  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.433  -0.095   0.845  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.841   1.148   1.315  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.871  -0.307  -0.588  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.476  -1.532  -1.073  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.864   0.699   0.320  1.00  0.00           C  
HETATM   10  O5  UNL     1       0.810   2.094   0.430  1.00  0.00           O  
HETATM   11  C6  UNL     1       1.716   0.098  -0.478  1.00  0.00           C  
HETATM   12  O6  UNL     1       2.676   0.712  -1.320  1.00  0.00           O  
HETATM   13  H1  UNL     1       0.298  -0.210   2.110  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.947  -0.862   1.459  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.187   1.501   1.965  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.420   0.493  -1.215  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.973  -0.248  -0.694  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.155  -1.483  -1.998  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.099   2.705  -0.324  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.619   0.680  -0.986  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5    9   13
CONECT    5    6    7   14
CONECT    6   15
CONECT    7    8   16   17
CONECT    8   18
CONECT    9   10   11   11
CONECT   10   19
CONECT   11   12
CONECT   12   20
END
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SMILES for #<Metabolite:0x00007f53b88aa8a0>

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
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INCHI for #<Metabolite:0x00007f53b88aa8a0>

InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
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Synonyms
Molecular FormulaC6H8O6
Average Mass176.1241
Monoisotopic Mass176.032087988
IUPAC Name(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional Namevitamin C
CAS Registry Number50-81-7
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1
InChI KeyCIWBSHSKHKDKBQ-JLAZNSOCSA-N