(S)-2-[(2,2-Dimethyl-cyclopropanecarbonyl)-amino]-8-(1-methyl-1-phosphono-ethylamino)-oct-2-enoic acid

ID: ALA1907818

PubChem CID: 57400121

Max Phase: Preclinical

Molecular Formula: C17H31N2O6P

Molecular Weight: 390.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCCNC(C)(C)P(=O)(O)O)C(=O)O

Standard InChI:  InChI=1S/C17H31N2O6P/c1-16(2)11-12(16)14(20)19-13(15(21)22)9-7-5-6-8-10-18-17(3,4)26(23,24)25/h9,12,18H,5-8,10-11H2,1-4H3,(H,19,20)(H,21,22)(H2,23,24,25)/b13-9-/t12-/m1/s1

Standard InChI Key:  QXBNNRXWIGCNPK-FNWMBBJUSA-N

Molfile:  

     RDKit          2D

 27 27  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
   -0.7881   -5.2834    0.0000 P   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
   -0.8006   -4.5786    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
   -1.6138   -5.2834    0.0000 O   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
    3.2526   -1.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -5.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -5.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -3.8572    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
    4.9914   -3.6321    0.0000 C   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
   -1.4720   -4.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -4.5786    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
    0.4253   -3.8447    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
    0.8299   -3.1275    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  8  1  0
  4  1  1  0
  1  5  1  1
  6  5  1  0
  7  6  1  0
  8 16  1  0
  9  7  1  0
 10  3  2  0
 11  5  2  0
 12  9  2  0
 13  7  2  0
 14  3  1  0
 15  3  1  0
 16 23  1  0
 17  9  1  0
 18  2  1  0
 19  2  1  0
 20  8  1  0
 21  8  1  0
 22 13  1  0
 23 25  1  0
 24 22  1  0
 25 26  1  0
 26 24  1  0
  2  4  1  0
  1 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1907818

   (Z)-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]-8-(2-phosphonopropan-2-ylamino)oct-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: 390.42

Molecular Weight (Monoisotopic): 390.1920

AlogP: 2.18

#Rotatable Bonds: 11

Polar Surface Area: 135.96

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.67

CX Basic pKa: 9.42

CX LogP: -0.36

CX LogD: -4.15

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.21

Np Likeness Score: 0.65

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