Marvin  02080816422D          

 14 15  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -0.6675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9841    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    1.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  2  0  0  0  0
  1  2  1  0  0  0  0
 14  2  1  0  0  0  0
  8  3  1  0  0  0  0
  4  3  2  0  0  0  0
  7  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  3  1  0  0  0  0
 12  5  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
 11  6  2  0  0  0  0
  9  7  1  0  0  0  0
 13  7  1  0  0  0  0
  9  8  2  0  0  0  0
M  END
> <ID>
CHEBI:27732

> <NAME>
caffeine

> <DEFINITION>
A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:3295; CHEBI:41472; CHEBI:22982

> <SYNONYM>
theine; Thein; teina; methyltheobromine; mateina; Koffein; guaranine; Coffein; caffeine; Caffeine; CAFFEINE; cafeine; cafeina; anhydrous caffeine; 7-methyltheophylline; 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion; 1-methyltheobromine; 1,3,7-trimethylxanthine; 1,3,7-Trimethylxanthine; 1,3,7-trimethylpurine-2,6-dione; 1,3,7-trimethyl-2,6-dioxopurine

> <IUPAC_NAME>
1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione

> <FORMULA>
C8H10N4O2

> <MASS>
194.19076

> <MONOISOTOPIC_MASS>
194.08038

> <CHARGE>
0

> <SMILES>
Cn1cnc2n(C)c(=O)n(C)c(=O)c12

> <INCHI>
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

> <INCHIKEY>
RYYVLZVUVIJVGH-UHFFFAOYSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
17705

> <CAS_REGISTRY_NUMBER>
58-08-2

> <GMELIN_REGISTRY_NUMBER>
103040

> <REAXYS_REGISTRY_NUMBER>
17705

> <CHEMIDPLUS>
58-08-2

> <DRUGBANK_ACCESSION>
DB00201

> <KEGG_COMPOUND_ACCESSION>
C07481

> <KEGG_DRUG_ACCESSION>
D00528

> <KNAPSACK_ACCESSION>
C00001492

> <LINCS_ACCESSION>
LSM-2026

> <METACYC_ACCESSION>
1-3-7-TRIMETHYLXANTHINE

> <NIST_CHEMISTRY_WEBBOOK>
58-08-2

> <PDBECHEM_ACCESSION>
CFF

> <WIKIPEDIA_ACCESSION>
Caffeine

> <PUBMED_CITATION>
10510174; 10796597; 10803761; 10822912; 10884512; 10924888; 10983026; 11014293; 11022879; 11209966; 11312039; 11410911; 11431501; 11815511; 11949272; 12397877; 12457274; 12574990; 12915014; 12943586; 14521986; 14607010; 15257305; 15280431; 15681408; 15718055; 15840517; 16143823; 16391865; 16528931; 16644114; 16709440; 16805851; 16856769; 17132260; 17387608; 17508167; 17724925; 17932622; 17957400; 18068204; 18258404; 18421070; 18513215; 18625110; 18647558; 19007524; 19047957; 19084078; 19088793; 19418355; 19879252; 20164568; 20470411; 22114686; 22770225; 23551936; 24039592; 7441110; 7689104; 8332255; 8347173; 8679661; 9063686; 9067318; 9132918; 9218278

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