Marvin  08051011492D          

 10 10  0  0  0  0            999 V2000
   -0.0125   -0.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636   -0.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    0.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -0.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4650   -0.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    0.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -1.2144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  9  8  1  0  0  0  0
  5  4  1  0  0  0  0
  6 10  1  0  0  0  0
M  END
> <ID>
CHEBI:412516

> <NAME>
5-hydroxymethylfurfural

> <DEFINITION>
A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:2077; CHEBI:42598

> <SYNONYM>
Hydroxymethylfurfurole; Hydroxymethylfurfuraldehyde; Hydroxymethylfurfuralaldehyde; Hydroxymethylfurfural; HMF; 5-Oxymethylfurfurole; 5-Hydroxymethylfurfuraldehyde; 5-hydroxymethylfurfural; 5-Hydroxymethylfuran-2-aldehyde; 5-Hydroxymethylfuraldehyde; 5-Hydroxymethyl-2-furfural; 5-Hydroxymethyl-2-furancarbaldehyde; 5-Hydroxymethyl-2-furaldehyde; 5-Hydroxymethyl-2-formylfuran; 5-HMF; 5-(Hydroxymethyl)furfurole; 5-(Hydroxymethyl)furfural; 5-(Hydroxymethyl)furan-2-aldehyde; 5-(Hydroxymethyl)-2-furfuraldehyde; 5-(Hydroxymethyl)-2-furfuraldehyde; 5-(Hydroxymethyl)-2-furfural; 5-(Hydroxymethyl)-2-furancarboxaldehyde; 5-(Hydroxymethyl)-2-furancarbonal; 5-(hydroxymethyl)-2-furaldehyde; 2-Hydroxymethyl-5-furfural

> <IUPAC_NAME>
5-(hydroxymethyl)furan-2-carbaldehyde

> <FORMULA>
C6H6O3

> <MASS>
126.11000

> <MONOISOTOPIC_MASS>
126.03169

> <CHARGE>
0

> <SMILES>
[H]C(=O)c1ccc(CO)o1

> <INCHI>
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2

> <INCHIKEY>
NOEGNKMFWQHSLB-UHFFFAOYSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
110889

> <CAS_REGISTRY_NUMBER>
67-47-0

> <GMELIN_REGISTRY_NUMBER>
278693

> <REAXYS_REGISTRY_NUMBER>
110889

> <CHEMIDPLUS>
67-47-0

> <KEGG_COMPOUND_ACCESSION>
C11101

> <KNAPSACK_ACCESSION>
C00029547

> <METACYC_ACCESSION>
CPD-11572

> <NIST_CHEMISTRY_WEBBOOK>
67-47-0

> <PDBECHEM_ACCESSION>
FUX

> <WIKIPEDIA_ACCESSION>
Hydroxymethylfurfural

> <PUBMED_CITATION>
1556177; 20082406; 20420424; 21838257; 22264628; 22757699; 22957895; 23106038; 24001819; 24054253; 24054256; 24399510; 24399607; 24408726; 24444020; 24518321; 25015917; 25333920; 25858076; 25922228; 28317713; 28395827; 2917974; 6391997

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