The pathway with the name Diazepam
 has the following structure: 
Result: 
CC(=O)[O-]
 C1=CC=C(C=C1)C(=O)C2=CC(=CC=C2NC(=O)CN)Cl
 no rule associatedCC(=O)NCC(=O)NC1=CC=C(C=C1C(=O)C2=CC=CC=C2)Cl
CN1C2=C(C=C(C=C2)Cl)C(=NCC1=O)C3=CC=CC=C3
 SimpleRule(uri = https://envipath.org/package/32de3cf4-e3e6-4168-956e-32fa5ddb0ce1/simple-rule/cce8f86d-1e79-491c-a577-e48ef8b5a849, SMIRKS = [#6:4]\[#6:1]@=[#7:2]\[#6:5]>>[#6:4]-[#6:1]=O.[#6:5]-[#7:2]) CN(C1=CC=C(C=C1C(=O)C2=CC=CC=C2)Cl)C(=O)CN
CN(C1=CC=C(C=C1C(=O)C2=CC=CC=C2)Cl)C(=O)CN
 CC(=O)[O-]
 no rule associatedCC(=O)NCC(=O)N(C)C1=CC=C(C=C1C(=O)C2=CC=CC=C2)Cl
C1=CC=C(C=C1)C2=NCC(=O)NC3=C2C=C(C=C3)Cl
 SimpleRule(uri = https://envipath.org/package/32de3cf4-e3e6-4168-956e-32fa5ddb0ce1/simple-rule/cce8f86d-1e79-491c-a577-e48ef8b5a849, SMIRKS = [#6:4]\[#6:1]@=[#7:2]\[#6:5]>>[#6:4]-[#6:1]=O.[#6:5]-[#7:2]) C1=CC=C(C=C1)C(=O)C2=CC(=CC=C2NC(=O)CN)Cl
CN1C2=C(C=C(C=C2)Cl)C(=NCC1=O)C3=CC=CC=C3
 SimpleRule(uri = https://envipath.org/package/32de3cf4-e3e6-4168-956e-32fa5ddb0ce1/simple-rule/bf030393-4fc7-40f1-aa21-e3a853ba26c8, SMIRKS = [#6,#7:6][#6:7](=[O:8])[#7;!$(N(CC)C(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)n1cnc2c(N)ncnc12)!$(NC(CCC(=O)NC(CS)C(=O)NCC([O-])=O)C([O-])=O):1]!@-[#6;A:2][H:3]>>[#6,#7:6][#6:7](=[O:8])[#7:1][H:3].[#6;A:2]=O) C1=CC=C(C=C1)C2=NCC(=O)NC3=C2C=C(C=C3)Cl

Description: Diazepam, 7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one, is a widely used drug. It is used as an anticonvulsant, sedative, and muscle relaxant, and has a long duration of action (PubChem, 2011). The fungus Aspergillus niger J/8 N-demethylates diazepam to form 7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-one. This demethylation step may be carried out by a transmethylase, hydrolytic demethylase or one of several different types of oxidative demethylases, so the generic "A" is used. The diazepin ring in the demethylated compound is then cleaved. It transiently forms 2-amino-N-(2-benzoyl-4-chlorophenyl)acetamide, which is N-acetylated to form N-(2-benzoyl-4-chlorophenyl)-2-acetamidoacetamide. The fungus Penicillium velutinum cleaves the diazepin ring at the same position without prior N-demethylation and performs the same N-acetylation, to form N-(2-benzoyl-4-chlorophenyl-2-acetamido-N-methylacetamide. Other fungi can demethylate diazepam, but this is the first report of fungal diazepam ring cleavage ([http://www.ncbi.nlm.nih.gov/pubmed/1168398|Ambrus et al. 1975]). A mixed microbial culture from activated sludge treatment has also been shown to demethylate diazepam to form 7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-one ([http://www.ncbi.nlm.nih.gov/pubmed/20799730|Helbling et al., 2010]). The same culture also formed a mono-hydroxylated diazepam derivative, but the exact position of the hydroxyl group was not further specified.
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