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Showing NP-Card for 3-Deoxyarabinohexonic acid (NP0001399)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:41:57 UTC
NP-MRD IDNP0001399
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Deoxyarabinohexonic acid
Description3-Deoxyarabinohexonic acid, also known as arabino-3-deoxyhexonate or D-2-keto-3-deoxygluconate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms. 3-Deoxyarabinohexonic acid is a thermal decomposition product of plant-derived sugars such as nigerose (3-O-α-D-glucopyranosyl-D-glucose), turanose and 3-O-methyl glucose. 3-Deoxyarabinohexonic acid is found in plants and plant products that have been heated. As a consequence, it can be detected in the biofluids of animals that have consumed plant foods (including humans).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001399 (3-Deoxyarabinohexonic acid)


  Mrv1652305261923572D          

 12 11  0  0  1  0            999 V2000
   12.8666  -15.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812  -13.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4378  -15.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0100  -14.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087  -15.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7232  -13.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8666  -15.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1522  -14.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812  -14.7440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4378  -15.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2956  -15.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7232  -14.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  9  2  1  6  0  0  0
 10  3  1  6  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0001399 (3-Deoxyarabinohexonic acid)

HMDB0000346
     RDKit          3D
3-Deoxyarabinohexonic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
    4.0876   -0.0739   -0.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    0.5626    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136    1.7594    0.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151    0.0457   -0.3631 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9136   -1.1631   -1.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267   -0.1942    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.7251    0.6262 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4604   -1.9238   -0.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    0.2683   -0.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3601    1.4942    0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -0.3494   -0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384    0.4605   -0.7925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    2.6631    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    0.7547   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -1.8728   -0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544    0.7049    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -0.9743    1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238   -0.9083    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -1.8009   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    0.4103   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.4356    1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.3211   -0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -0.5417    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8568    1.2892   -0.3322 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
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
  3 13  1  0
  4 14  1  6
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  6
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0001399 (3-Deoxyarabinohexonic acid)


  Mrv1652305261923572D          

 12 11  0  0  1  0            999 V2000
   12.8666  -15.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812  -13.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4378  -15.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0100  -14.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087  -15.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7232  -13.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8666  -15.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1522  -14.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5812  -14.7440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4378  -15.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2956  -15.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7232  -14.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  9  2  1  6  0  0  0
 10  3  1  6  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001399

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1

> <INCHI_KEY>
YGMNHEPVTNXLLS-VAYJURFESA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.381679693405605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-2.719449629666667

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.269276438065713

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5711021403725516

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9720910002599323

> <JCHEM_POLAR_SURFACE_AREA>
118.22

> <JCHEM_REFRACTIVITY>
37.17390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-deoxy-arabinohexonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001399 (3-Deoxyarabinohexonic acid)

HMDB0000346
     RDKit          3D
3-Deoxyarabinohexonic acid
 24 23  0  0  0  0  0  0  0  0999 V2000
    4.0876   -0.0739   -0.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    0.5626    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136    1.7594    0.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7151    0.0457   -0.3631 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9136   -1.1631   -1.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267   -0.1942    0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.7251    0.6262 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4604   -1.9238   -0.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    0.2683   -0.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3601    1.4942    0.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384   -0.3494   -0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384    0.4605   -0.7925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    2.6631    0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    0.7547   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -1.8728   -0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544    0.7049    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -0.9743    1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238   -0.9083    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -1.8009   -1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    0.4103   -1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.4356    1.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.3211   -0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -0.5417    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8568    1.2892   -0.3322 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
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
  3 13  1  0
  4 14  1  6
  5 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  6
 10 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

PDB for NP0001399 (3-Deoxyarabinohexonic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      24.018 -29.832   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      25.352 -25.982   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.351 -29.832   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.019 -27.522   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      18.683 -28.292   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      20.017 -25.982   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      24.018 -28.292   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.684 -27.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.352 -27.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.351 -28.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.685 -28.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.017 -27.522   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   12                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    2    7   11                                                  
CONECT   10    3    8   12                                                  
CONECT   11    4    9                                                       
CONECT   12    5    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0001399 (3-Deoxyarabinohexonic acid)

COMPND    HMDB0000346
HETATM    1  O1  UNL     1       4.088  -0.074  -0.234  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.046   0.563   0.037  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.214   1.759   0.722  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.715   0.046  -0.363  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.914  -1.163  -1.025  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.927  -0.194   0.897  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.457  -0.725   0.626  1.00  0.00           C  
HETATM    8  O4  UNL     1      -0.460  -1.924  -0.047  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.339   0.268  -0.082  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.360   1.494   0.572  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.738  -0.349  -0.127  1.00  0.00           C  
HETATM   12  O6  UNL     1      -3.638   0.461  -0.793  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.060   2.663   0.344  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.210   0.755  -1.052  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.212  -1.873  -0.420  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.854   0.705   1.514  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.462  -0.974   1.478  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.924  -0.908   1.626  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.336  -1.801  -1.031  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.967   0.410  -1.102  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.883   1.436   1.409  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.671  -1.321  -0.626  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.069  -0.542   0.920  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.857   1.289  -0.332  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    6   14
CONECT    5   15
CONECT    6    7   16   17
CONECT    7    8    9   18
CONECT    8   19
CONECT    9   10   11   20
CONECT   10   21
CONECT   11   12   22   23
CONECT   12   24
END
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SMILES for NP0001399 (3-Deoxyarabinohexonic acid)

OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O
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INCHI for NP0001399 (3-Deoxyarabinohexonic acid)

InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1
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View in JSmol
Synonyms
ValueSource
(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoic acidChEBI
3-Deoxy-arabino-hexonic acidChEBI
3-Deoxyarabino-hexonic acidChEBI
(2S,4S,5R)-2,4,5,6-TetrahydroxyhexanoateGenerator
3-Deoxy-arabino-hexonateGenerator
3-Deoxyarabino-hexonateGenerator
3-DeoxyarabinohexonateGenerator
3-Deoxy-D-arabino-hexonic acidHMDB
Arabino-3-deoxyhexonateHMDB
Arabino-3-deoxyhexonic acidHMDB
D-2-Keto-3-deoxygluconateHMDB
3-Deoxy-arabino-hexonic acid, monosodium salt, (D)-isomerHMDB
3-Deoxy-arabino-hexonic acid, (D)-isomerHMDB
3-Deoxy-D-arabino-hexonateHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid
Traditional Name3-deoxy-arabinohexonic acid
CAS Registry Number29625-79-4
SMILES
OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1
InChI KeyYGMNHEPVTNXLLS-VAYJURFESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-10View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility255 g/LALOGPS
logP-2.5ALOGPS
logP-2.7ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.17 m³·mol⁻¹ChemAxon
Polarizability16.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000346
DrugBank IDDB03303
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021969
KNApSAcK IDNot Available
Chemspider ID134838
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5335
PubChem Compound152990
PDB IDSSH
ChEBI ID45626
Good Scents IDNot Available
References
General References
  1. Theodossis A, Walden H, Westwick EJ, Connaris H, Lamble HJ, Hough DW, Danson MJ, Taylor GL: The structural basis for substrate promiscuity in 2-keto-3-deoxygluconate aldolase from the Entner-Doudoroff pathway in Sulfolobus solfataricus. J Biol Chem. 2004 Oct 15;279(42):43886-92. doi: 10.1074/jbc.M407702200. Epub 2004 Jul 20. [PubMed:15265860 ]
  2. Zhang W, Carmichael I, Serianni AS: Rearrangement of 3-deoxy-D-erythro-hexos-2-ulose in aqueous solution: NMR evidence of intramolecular 1,2-hydrogen transfer. J Org Chem. 2011 Oct 21;76(20):8151-8. doi: 10.1021/jo200288t. Epub 2011 Sep 20. [PubMed:21793547 ]