Marvin  04021315082D          

 14 14  0  0  1  0            999 V2000
    8.2473   -7.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9461   -7.8581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8439   -6.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6575   -6.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5448   -7.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6484   -7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3473   -7.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6519   -6.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0496   -7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7520   -7.8581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4509   -7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7554   -8.6717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1497   -7.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4543   -6.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  1  0  0  0
 11 13  1  0  0  0  0
 11 14  2  0  0  0  0
  3  4  1  0  0  0  0
M  END
> <ID>
CHEBI:3875

> <NAME>
coprine

> <DEFINITION>
A non-proteinogenic L-α-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Coprinus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect').

> <STAR>
3

> <SYNONYM>
N(5)-(1-hydroxycyclopropyl)-L-glutamine; L-coprine; (2S)-2,5-diamino-5-oxopentanoic acid

> <IUPAC_NAME>
N-(1-hydroxycyclopropyl)-L-glutamine

> <FORMULA>
C8H14N2O4

> <MASS>
202.20780

> <MONOISOTOPIC_MASS>
202.09536

> <CHARGE>
0

> <SMILES>
N[C@@H](CCC(=O)NC1(O)CC1)C(O)=O

> <INCHI>
InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1

> <INCHIKEY>
OEEZRBUCLFMTLD-YFKPBYRVSA-N

> <CAS_REGISTRY_NUMBER>
58919-61-2

> <REAXYS_REGISTRY_NUMBER>
2053887

> <CHEMIDPLUS>
58919-61-2

> <KEGG_COMPOUND_ACCESSION>
C08271

> <KNAPSACK_ACCESSION>
C00001349

> <PUBMED_CITATION>
1241098; 1553385; 2474765; 350009; 473235; 558210; 577107; 7097272; 7159468

$$$$