Marvin  11150718482D          

 12 11  0  0  1  0            999 V2000
   -0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  1  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
> <ID>
CHEBI:16349

> <NAME>
L-citrulline

> <DEFINITION>
The L-enantiomer of citrulline.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:41489; CHEBI:6203; CHEBI:13092; CHEBI:21257

> <SYNONYM>
N(delta)-carbamylornithine; N5-carbamoylornithine; N5-(Aminocarbonyl)ornithine; N(5)-(aminocarbonyl)-L-ornithine; L-Citrulline; L-2-Amino-5-ureidovaleric acid; delta-ureidonorvaline; Citrulline; CITRULLINE; Cit; alpha-amino-delta-ureidovaleric acid; 2-Amino-5-ureidovaleric acid; (S)-2-Amino-5-ureidopentanoic acid

> <IUPAC_NAME>
N(5)-carbamoyl-L-ornithine; L-citrulline; (2S)-2-amino-5-(carbamoylamino)pentanoic acid

> <FORMULA>
C6H13N3O3

> <MASS>
175.18584

> <MONOISOTOPIC_MASS>
175.09569

> <CHARGE>
0

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

> <INCHI>
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1

> <INCHIKEY>
RHGKLRLOHDJJDR-BYPYZUCNSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
6055157

> <CAS_REGISTRY_NUMBER>
372-75-8

> <GMELIN_REGISTRY_NUMBER>
774677

> <REAXYS_REGISTRY_NUMBER>
1725416

> <CHEMIDPLUS>
372-75-8

> <DRUGBANK_ACCESSION>
DB00155

> <ECMDB_ACCESSION>
ECMDB00904

> <KEGG_COMPOUND_ACCESSION>
C00327

> <KEGG_DRUG_ACCESSION>
D07706

> <KNAPSACK_ACCESSION>
C00001348

> <METACYC_ACCESSION>
L-CITRULLINE

> <PDBECHEM_ACCESSION>
CIR

> <WIKIPEDIA_ACCESSION>
Citrulline

> <YMDB_ACCESSION>
YMDB00060

> <PUBMED_CITATION>
11862757; 17190852; 18022291; 19173225; 21067832; 21915076; 21955999; 22119809; 22345866; 22348173; 22387109; 22388927; 22402328; 22402472; 22512552

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