Showing metabocard for L-Gulono-1,4-lactone (MMDBc0033139)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:36:18 UTC
Update Date2024-04-30 20:01:06 UTC
Metabolite IDMMDBc0033139
Metabolite Identification
Common NameL-Gulono-1,4-lactone
DescriptionL-Gulono-1,4-lactone, also known as L-gulonolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. L-Gulono-1,4-lactone exists in all living species, ranging from bacteria to plants to humans. L-Gulono-1,4-lactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-Gulono-1,4-lactone a potential biomarker for the consumption of these foods. L-Gulono-1,4-lactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-Gulono-1,4-lactone.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9234012b88>


  Mrv1652309182018542D          

 13 13  0  0  0  0            999 V2000
10000.718610000.5377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.432810000.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.718610001.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.149210000.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2108 9998.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4175 9998.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880710000.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6360 9999.5943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.331310000.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.663910000.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9188 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.7438 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.998710000.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  2  4  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13  8  1  1  0  0  0
 12  5  1  6  0  0  0
 11  6  1  6  0  0  0
 10  7  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9234012b88>

HMDB0003466
     RDKit          3D
L-Gulonolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.5607   -1.8438   -1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185   -1.1080   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.0436   -1.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351    0.2586   -1.1198 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4705    0.2085   -0.4324 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9925    1.4431   -0.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.6722    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.7883    1.1893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.9247   -0.3432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5530    1.4465    0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063   -0.1406   -0.0982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8041   -0.6719    1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663    0.7678   -2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -0.2822   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712    1.4003   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734   -0.2448    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.6975    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -0.8574    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7403   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    2.1219    1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    0.2905   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5439   -1.2520    1.4352 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  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  6
  5 14  1  6
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  6
 10 20  1  0
 11 21  1  1
 12 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9234012b88>


  Mrv1652309182018542D          

 13 13  0  0  0  0            999 V2000
10000.718610000.5377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.432810000.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.718610001.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.149210000.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2108 9998.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4175 9998.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880710000.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6360 9999.5943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.331310000.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.663910000.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9188 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.7438 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.998710000.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  2  4  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13  8  1  1  0  0  0
 12  5  1  6  0  0  0
 11  6  1  6  0  0  0
 10  7  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033139

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

> <INCHI_KEY>
SXZYCXMUPBBULW-SKNVOMKLSA-N

> <FORMULA>
C6H10O6

> <MOLECULAR_WEIGHT>
178.14

> <EXACT_MASS>
178.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.465415844188865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.745273186

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.172871312116015

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.623539809865173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974938008499871

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
34.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-gulonolactone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9234012b88>

HMDB0003466
     RDKit          3D
L-Gulonolactone
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.5607   -1.8438   -1.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185   -1.1080   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -1.0436   -1.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351    0.2586   -1.1198 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4705    0.2085   -0.4324 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9925    1.4431   -0.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752   -0.6722    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.7883    1.1893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365    0.9247   -0.3432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5530    1.4465    0.8669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063   -0.1406   -0.0982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8041   -0.6719    1.1613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663    0.7678   -2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783   -0.2822   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712    1.4003   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734   -0.2448    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.6975    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8898   -0.8574    2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7403   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2421    2.1219    1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339    0.2905   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5439   -1.2520    1.4352 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  1  0
 11 12  1  0
 11  2  1  0
  4 13  1  6
  5 14  1  6
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  6
 10 20  1  0
 11 21  1  1
 12 22  1  0
M  END
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PDB for #<Metabolite:0x00007f9234012b88>

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0088667.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3418666.900   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.0088669.212   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.6798667.670   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.0608664.196   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.7138664.211   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.7118667.377   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8667.8548665.909   0.000  0.00  0.00           H+0
HETATM    9  O   UNK     0    8665.4188667.822   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8664.1738666.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6488665.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.1888665.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6648666.917   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5   12                                                            
CONECT    6   11                                                            
CONECT    7   10                                                            
CONECT    8   13                                                            
CONECT    9   10   13                                                       
CONECT   10   11    9    7                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12    9    1    8                                             
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f9234012b88>

COMPND    HMDB0003466
HETATM    1  O1  UNL     1      -2.561  -1.844  -1.801  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.718  -1.108  -1.183  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.344  -1.044  -1.382  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.135   0.259  -1.120  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.470   0.208  -0.432  1.00  0.00           C  
HETATM    6  O3  UNL     1       1.992   1.443  -0.149  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.475  -0.672   0.792  1.00  0.00           C  
HETATM    8  O4  UNL     1       2.824  -0.788   1.189  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.937   0.925  -0.343  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.553   1.447   0.867  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.006  -0.141  -0.098  1.00  0.00           C  
HETATM   12  O6  UNL     1      -1.804  -0.672   1.161  1.00  0.00           O  
HETATM   13  H1  UNL     1       0.266   0.768  -2.086  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.178  -0.282  -1.164  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.971   1.400  -0.025  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.873  -0.245   1.621  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.127  -1.697   0.539  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.890  -0.857   2.177  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.460   1.740  -0.920  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.242   2.122   1.131  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.034   0.290  -0.209  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.544  -1.252   1.435  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   19
CONECT   10   20
CONECT   11   12   21
CONECT   12   22
END
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SMILES for #<Metabolite:0x00007f9234012b88>

[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO
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INCHI for #<Metabolite:0x00007f9234012b88>

InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1
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Synonyms
ValueSource
gamma-GulonolactoneChEBI
L-Gulonic acid gamma-lactoneChEBI
L-Gulono-gamma-lactoneChEBI
g-GulonolactoneGenerator
Γ-gulonolactoneGenerator
L-Gulonate g-lactoneGenerator
L-Gulonate gamma-lactoneGenerator
L-Gulonate γ-lactoneGenerator
L-Gulonic acid g-lactoneGenerator
L-Gulonic acid γ-lactoneGenerator
L-Gulono-g-lactoneGenerator
L-Gulono-γ-lactoneGenerator
L-(+)-gulono-1,4-LactoneHMDB
L-Gulono-1,4-lactoneHMDB
Reduced ascorbateHMDB
Reduced ascorbic acidHMDB
Gulonolactone, (L)-isomerMeSH, HMDB
GulonolactoneMeSH, HMDB
Gulonolactone, (D)-isomerMeSH, HMDB
Dihydroascorbic acidHMDB
L-(+)-Gulonic acid gamma-lactoneHMDB
L-(+)-Gulonic acid γ-lactoneHMDB
L-GulonolactoneHMDB
Molecular FormulaC6H10O6
Average Mass178.14
Monoisotopic Mass178.047738052
IUPAC Name(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one
Traditional NameL-gulonolactone
CAS Registry Number1128-23-0
SMILES
[H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO
InChI Identifier
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1
InChI KeySXZYCXMUPBBULW-SKNVOMKLSA-N