Showing metabocard for Erythritol (MMDBc0000225)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:40:26 UTC
Update Date2024-04-30 19:31:34 UTC
Metabolite IDMMDBc0000225
Metabolite Identification
Common NameErythritol
DescriptionErythritol occurs widely in nature and has been found to occur naturally in several foods including wine, sake, beer, watermelon, pear, grape, and soy sauce. Evidence indicates that erythritol also exists endogenously in the tissues and body fluids of humans and animals. Erythritol is absorbed from the proximal intestine by passive diffusion in a manner similar to that of many low molecular weight organic molecules which do not have associated active transport systems. The rate of absorption is related to their molecular size; erythritol, a 4-carbon molecule, passes through the intestinal membranes at a faster rate than larger molecules such as mannitol or glucose. In diabetics, erythritol has also been shown to be rapidly absorbed and excreted unchanged in the urine. Following absorption, ingested erythritol is rapidly distributed throughout the body and has been reported to occur in hepatocytes, pancreatic cells, and vascular smooth muscle cells. Erythritol also has been reported to cross the human placenta and to pass slowly from the plasma into the brain and cerebrospinal fluid (PMID: 9862657 , Food and Chemical Toxicology (1998), 36(12), 1139-1174.). Erythritol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecb0602760>


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
   -1.7855    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710    1.1830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0710    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3565    2.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723    1.5955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  5  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  1  0  0  0
  7  8  1  0  0  0  0
  3  4  1  6  0  0  0
  2  1  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fecb0602760>

HMDB0002994
     RDKit          3D
Erythritol
 18 17  0  0  0  0  0  0  0  0999 V2000
    1.9905    1.3531   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574    0.0950   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226   -0.6627    0.3646 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4855   -1.9045   -0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    0.0868    0.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0925   -0.6618    1.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    0.2592   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    0.9164   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    2.0599   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281    0.1473   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -0.4824   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -0.7977    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.6250    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115    1.0724    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8686   -0.1802    2.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397   -0.7597   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383    0.7712   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9158    1.3129   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  1
  4 13  1  0
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007fecb0602760>


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
   -1.7855    1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.1830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710    1.1830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0710    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565    1.5955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3565    2.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723    1.5955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  3  5  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  1  0  0  0
  7  8  1  0  0  0  0
  3  4  1  6  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000225

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+

> <INCHI_KEY>
UNXHWFMMPAWVPI-ZXZARUISSA-N

> <FORMULA>
C4H10O4

> <MOLECULAR_WEIGHT>
122.1198

> <EXACT_MASS>
122.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.623273435855882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-butane-1,2,3,4-tetrol

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-2.4693489646666666

> <ALOGPS_LOGS>
0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.285181811808233

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.044993073077713

> <JCHEM_PKA_STRONGEST_BASIC>
-2.973906601202132

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
26.478599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythritol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fecb0602760>

HMDB0002994
     RDKit          3D
Erythritol
 18 17  0  0  0  0  0  0  0  0999 V2000
    1.9905    1.3531   -0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574    0.0950   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226   -0.6627    0.3646 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4855   -1.9045   -0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    0.0868    0.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0925   -0.6618    1.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    0.2592   -0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960    0.9164   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    2.0599   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281    0.1473   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -0.4824   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -0.7977    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -2.6250    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115    1.0724    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8686   -0.1802    2.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397   -0.7597   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383    0.7712   -1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9158    1.3129   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  1
  4 13  1  0
  5 14  1  1
  6 15  1  0
  7 16  1  0
  7 17  1  0
  8 18  1  0
M  END
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PDB for #<Metabolite:0x00007fecb0602760>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.333   2.978   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.667   2.208   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.999   2.208   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.999   0.668   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.665   2.978   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.665   4.518   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.668   2.208   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.002   2.978   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1                                                            
CONECT    3    1    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007fecb0602760>

COMPND    HMDB0002994
HETATM    1  O1  UNL     1       1.991   1.353  -0.144  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.657   0.095  -0.656  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.823  -0.663   0.365  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.485  -1.904  -0.123  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.431   0.087   0.727  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.092  -0.662   1.701  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.353   0.259  -0.461  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.496   0.916  -0.056  1.00  0.00           O  
HETATM    9  H1  UNL     1       1.635   2.060  -0.708  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.128   0.147  -1.617  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.610  -0.482  -0.767  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.404  -0.798   1.297  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.113  -2.625   0.145  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.212   1.072   1.185  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.869  -0.180   2.070  1.00  0.00           H  
HETATM   16  H8  UNL     1      -1.640  -0.760  -0.806  1.00  0.00           H  
HETATM   17  H9  UNL     1      -0.838   0.771  -1.293  1.00  0.00           H  
HETATM   18  H10 UNL     1      -2.916   1.313  -0.859  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3   10   11
CONECT    3    4    5   12
CONECT    4   13
CONECT    5    6    7   14
CONECT    6   15
CONECT    7    8   16   17
CONECT    8   18
END
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SMILES for #<Metabolite:0x00007fecb0602760>

OC[C@H](O)[C@H](O)CO
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INCHI for #<Metabolite:0x00007fecb0602760>

InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+
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Synonyms
ValueSource
(2R,3S)-Butane-1,2,3,4-tetrolChEBI
ErythritChEBI
ErythriteChEBI
Erythro-tetritolChEBI
ErythrolChEBI
L-ErythritolChEBI
MESO-erythritolChEBI
MesoerythritolChEBI
PhyciteChEBI
PhycitolChEBI
1,2,3,4-ButanetetrolHMDB
AntierythriteHMDB
ButanetetrolHMDB
C*EridexHMDB
ErythroglucinHMDB
I-erythritolHMDB
L-(-)-ThreitolHMDB
L-ThreitolHMDB
Lichen sugarHMDB
Meso-eythritolHMDB
PayciteHMDB
TetrahydroxybutaneHMDB
1,2,3,4-TetrahydroxybutaneHMDB
Molecular FormulaC4H10O4
Average Mass122.1198
Monoisotopic Mass122.057908808
IUPAC Name(2R,3S)-butane-1,2,3,4-tetrol
Traditional Nameerythritol
CAS Registry Number149-32-6
SMILES
OC[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+
InChI KeyUNXHWFMMPAWVPI-ZXZARUISSA-N