(S)-2-acetylamino-3-{6-carboxy-6-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hex-5-enylsulfanyl}-propionate

ID: ALA1907817

PubChem CID: 57394926

Max Phase: Preclinical

Molecular Formula: C18H27N2NaO6S

Molecular Weight: 400.50

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)NC(CSCCCC/C=C(\NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C18H28N2O6S.Na/c1-11(21)19-14(17(25)26)10-27-8-6-4-5-7-13(16(23)24)20-15(22)12-9-18(12,2)3;/h7,12,14H,4-6,8-10H2,1-3H3,(H,19,21)(H,20,22)(H,23,24)(H,25,26);/q;+1/p-1/b13-7-;/t12-,14?;/m1./s1

Standard InChI Key:  ULJMRJSJBJICNW-LKYMUALQSA-M

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.0976   -5.5324    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.7701   -3.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909   -3.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4955   -3.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323   -2.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068   -2.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0691   -1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -4.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6259   -4.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3752   -5.2823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4169   -5.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7200   -1.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -5.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512   -3.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -0.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2519   -1.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -4.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2823   -0.9005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699   -4.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9904   -3.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -3.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -3.8439    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379   -6.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -2.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8297   -3.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554   -2.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6552   -3.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2802   -2.3784    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  2  5  1  1
  6  5  1  0
  7  6  1  0
  8 22  1  0
  9  8  1  0
 10  7  1  0
 11  8  1  0
 12 11  1  0
 13  5  2  0
 14  9  1  0
 15  9  2  0
 16 10  2  0
 17  7  2  0
 18 12  2  0
 19 10  1  0
 20  3  1  0
 21  3  1  0
 22 23  1  0
 23 26  1  0
 24 12  1  0
 25 17  1  0
 26 28  1  0
 27 25  1  0
 28 27  1  0
  3  4  1  0
  2 29  1  6
M  CHG  2   1   1  14  -1
M  END

Associated Targets(non-human)

DPEP1 Renal dipeptidase (518 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: 400.50Molecular Weight (Monoisotopic): 400.1668AlogP: 1.61#Rotatable Bonds: 12
Polar Surface Area: 132.80Molecular Species: ACIDHBA: 5HBD: 4
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 3.82CX Basic pKa: CX LogP: 0.94CX LogD: -5.22
Aromatic Rings: Heavy Atoms: 27QED Weighted: 0.29Np Likeness Score: 0.48

References

1. Graham DW, Ashton WT, Barash L, Brown JE, Brown RD, Canning LF, Chen A, Springer JP, Rogers EF..  (1987)  Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids.,  30  (6): [PMID:3495664] [10.1021/jm00389a018]

Source