BJM

(2~{S})-2-azanyl-1-[(1~{S},3~{S},5~{S})-3-(iminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-2-[(5~{R},7~{S})-3-oxidanyl-1-ad amantyl]ethanone

Created: 2007-12-13
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count50
Chiral Atom Count6
Bond Count54
Aromatic Bond Count0
2D diagram of BJM
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Chemical Component Summary

Name(2~{S})-2-azanyl-1-[(1~{S},3~{S},5~{S})-3-(iminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-2-[(5~{R},7~{S})-3-oxidanyl-1-ad amantyl]ethanone
SynonymsSaxagliptin, bound form
Systematic Name (OpenEye OEToolkits)(2~{S})-2-azanyl-1-[(1~{S},3~{S},5~{S})-3-(iminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-2-[(5~{R},7~{S})-3-oxidanyl-1-adamantyl]ethanone
FormulaC18 H27 N3 O2
Molecular Weight317.426
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385N[CH](C(=O)N1[CH](C[CH]2C[CH]12)C=N)C34C[CH]5C[CH](CC(O)(C5)C3)C4
SMILESOpenEye OEToolkits2.0.6C1C2CC2N(C1C=N)C(=O)C(C34CC5CC(C3)CC(C5)(C4)O)N
Canonical SMILESCACTVS3.385 N[C@H](C(=O)N1[C@@H](C[C@@H]2C[C@H]12)C=N)C34C[C@H]5C[C@H](CC(O)(C5)C3)C4
Canonical SMILESOpenEye OEToolkits2.0.6 C1[C@@H]2C[C@@H]2N([C@@H]1C=N)C(=O)[C@H](C34C[C@H]5C[C@@H](C3)CC(C5)(C4)O)N
InChIInChI1.03 InChI=1S/C18H27N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h8,10-15,19,23H,1-7,9,20H2/t10-,11+,12-,13+,14+,15-,17+,18-/m1/s1
InChIKeyInChI1.03 KMSQNYQXZPWGMJ-YQBUGCKMSA-N

Drug Info: DrugBank

DrugBank IDDB07465 
Name(1S,3S,5S)-2-{(2S)-2-amino-2-[(1R,3S,5R,7S)-3-hydroxytricyclo[3.3.1.1~3,7~]dec-1-yl]acetyl}-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Groups experimental
Synonyms(1S,3S,5S)-2-{(2S)-2-amino-2-[(1R,3S,5R,7S)-3-hydroxytricyclo[3.3.1.1~3,7~]dec-1-yl]acetyl}-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Drug Targets

NameTarget SequencePharmacological ActionActions
Dipeptidyl peptidase 4MKTPWKVLLGLLGAAALVTIITVPVVLLNKGTDDATADSRKTYTLTDYLK...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682