(S)-7-(2-Carboxy-2-methylamino-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid

ID: ALA1907816

PubChem CID: 57401925

Max Phase: Preclinical

Molecular Formula: C17H28N2O5S

Molecular Weight: 372.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(CSCCCC/C=C(\NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C17H28N2O5S/c1-17(2)9-11(17)14(20)19-12(15(21)22)7-5-4-6-8-25-10-13(18-3)16(23)24/h7,11,13,18H,4-6,8-10H2,1-3H3,(H,19,20)(H,21,22)(H,23,24)/b12-7-/t11-,13?/m1/s1

Standard InChI Key:  JNKGDPILBVXTRW-DVJJTCDSSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    5.7712   -3.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921   -3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4968   -3.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3334   -2.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078   -2.3435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -1.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577   -0.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -4.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006   -4.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -3.8823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -1.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -5.2834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834   -0.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -5.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -4.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9914   -3.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -3.8447    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -3.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -2.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170   -5.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558   -2.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -3.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2814   -2.3791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  1  4  1  1
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  9  1  0
  9 20  1  0
 10  4  2  0
 11  7  2  0
 12  8  2  0
 13  6  2  0
 14  9  1  0
 15  7  1  0
 16  8  1  0
 17  2  1  0
 18  2  1  0
 19 23  1  0
 20 19  1  0
 21 13  1  0
 22 14  1  0
 23 25  1  0
 24 21  1  0
 25 24  1  0
  2  3  1  0
  1 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1907816

   (Z)-7-[2-carboxy-2-(methylamino)ethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.49

Molecular Weight (Monoisotopic): 372.1719

AlogP: 1.69

#Rotatable Bonds: 12

Polar Surface Area: 115.73

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.15

CX Basic pKa: 9.99

CX LogP: -0.99

CX LogD: -3.97

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.30

Np Likeness Score: 0.67

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

Source(1):

• Scientific Literature