Marvin  02091117112D          

 19 19  0  0  1  0            999 V2000
   12.3674  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542  -12.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0805  -12.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3674  -11.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6542  -13.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9376  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7972  -12.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0805  -11.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7937  -11.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -11.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2200  -11.7118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9366  -11.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2200  -12.5347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6463  -11.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9366  -10.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9357  -11.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2137  -11.3068    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3791  -14.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3793  -15.0110    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 15  2  0  0  0  0
  8  9  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <ID>
CHEBI:28876

> <NAME>
melphalan

> <DEFINITION>
A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:25815; CHEBI:6742

> <SYNONYM>
Phenylalanine nitrogen mustard; Phenylalanine mustard; p-N-Bis(2-chloroethyl)amino-L-phenylalanine; p-N,N-bis(2-chloroethyl)amino-L-phenylalanine; p-L-Sarcolysin; p-Di-(2-chloroethyl)amino-L-phenylalanine; p-Bis(beta-chloroethyl)aminophenylalanine; L-Sarcolysine; L-Phenylalanine mustard; L-PAM; L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine; 4-(Bis(2-chloroethyl)amino)-L-phenylalanine; 3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine; 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine

> <IUPAC_NAME>
4-[bis(2-chloroethyl)amino]-L-phenylalanine

> <INN>
melphalanum; melphalan; melfalano

> <FORMULA>
C13H18Cl2N2O2

> <MASS>
305.20000

> <MONOISOTOPIC_MASS>
304.07453

> <CHARGE>
0

> <SMILES>
N[C@@H](Cc1ccc(cc1)N(CCCl)CCCl)C(O)=O

> <INCHI>
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1

> <INCHIKEY>
SGDBTWWWUNNDEQ-LBPRGKRZSA-N

> <CAS_REGISTRY_NUMBER>
148-82-3

> <REAXYS_REGISTRY_NUMBER>
2816456

> <CHEMIDPLUS>
148-82-3

> <DRUGBANK_ACCESSION>
DB01042

> <KEGG_DRUG_ACCESSION>
D00369

> <WIKIPEDIA_ACCESSION>
Melphalan

> <PUBMED_CITATION>
10820424; 10937717; 11680815; 11914777; 18481314; 445303; 7494795; 7605343; 8552138; 8951232; 9218926; 9250538

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