(2S,3aS,6aS)-1-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]octahydrocyclopenta[b]pyrrole-2-carbonitrile

ID: ALA3330073

PubChem CID: 118712788

Max Phase: Preclinical

Molecular Formula: C18H20F3N3O

Molecular Weight: 351.37

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N#C[C@@H]1C[C@@H]2CCC[C@@H]2N1C(=O)C[C@H](N)Cc1cc(F)c(F)cc1F

Standard InChI:  InChI=1S/C18H20F3N3O/c19-14-8-16(21)15(20)6-11(14)4-12(23)7-18(25)24-13(9-22)5-10-2-1-3-17(10)24/h6,8,10,12-13,17H,1-5,7,23H2/t10-,12+,13-,17-/m0/s1

Standard InChI Key:  LVDNNHBINPPRBD-IMODNSLOSA-N

Molfile:  

     RDKit          2D

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   11.7477  -18.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4557  -18.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1654  -18.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1625  -17.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4539  -17.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8737  -18.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5808  -18.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2891  -18.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5795  -17.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9962  -18.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7045  -18.9444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9949  -17.7197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7915  -19.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5911  -19.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1880  -20.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5817  -20.8501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4508  -18.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9948  -19.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7374  -18.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6522  -18.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8571  -17.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0372  -17.8957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7005  -19.6208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0410  -17.3139    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4555  -19.7680    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4515  -16.4962    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  1
  9 11  1  0
 11 12  1  0
 11 13  2  0
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 15 19  1  0
 18 12  1  0
 16 17  3  0
 14 16  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 23  1  6
 19 24  1  6
  1 25  1  0
  3 26  1  0
  6 27  1  0
M  END

Alternative Forms

  1. Parent:

    ALA3330073

    ---

Associated Targets(Human)

DPP7 Tchem Dipeptidyl peptidase II (2000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DPP4 Tclin Dipeptidyl peptidase IV (7109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DPP8 Tchem Dipeptidyl peptidase VIII (2139 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DPP9 Tchem Dipeptidyl peptidase IX (1624 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FAP Tchem Fibroblast activation protein alpha (827 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 351.37Molecular Weight (Monoisotopic): 351.1558AlogP: 2.66#Rotatable Bonds: 4
Polar Surface Area: 70.12Molecular Species: BASEHBA: 3HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.78CX LogP: 2.22CX LogD: 0.83
Aromatic Rings: 1Heavy Atoms: 25QED Weighted: 0.85Np Likeness Score: -0.46

References

1. Ji X, Xia C, Wang J, Su M, Zhang L, Dong T, Li Z, Wan X, Li J, Li J, Zhao L, Gao Z, Jiang H, Liu H..  (2014)  Design, synthesis and biological evaluation of 4-fluoropyrrolidine-2-carbonitrile and octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives as dipeptidyl peptidase IV inhibitors.,  86  [PMID:25164763] [10.1016/j.ejmech.2014.08.059]

Source