(S)-2-(((R)-1-Carboxy-3-methylbutoxy)carbonylamino)pentanedioic acid

ID: ALA4587808

PubChem CID: 155567546

Max Phase: Preclinical

Molecular Formula: C12H19NO8

Molecular Weight: 305.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](OC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C12H19NO8/c1-6(2)5-8(11(18)19)21-12(20)13-7(10(16)17)3-4-9(14)15/h6-8H,3-5H2,1-2H3,(H,13,20)(H,14,15)(H,16,17)(H,18,19)/t7-,8+/m0/s1

Standard InChI Key:  GCAXQXOSZUNUBK-JGVFFNPUSA-N

Molfile:  

 
     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   27.6400   -4.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3478   -3.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9282   -3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6400   -5.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0596   -4.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3478   -3.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6359   -2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6359   -1.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9282   -3.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7714   -3.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4833   -4.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7714   -3.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1951   -3.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9069   -4.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1951   -3.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9069   -2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9069   -1.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6188   -1.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1951   -1.4734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9069   -5.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6188   -3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  2  5  1  0
  2  6  1  1
  6  7  1  0
  7  8  1  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 14 20  2  0
 14 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4587808

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 305.28

Molecular Weight (Monoisotopic): 305.1111

AlogP: 0.53

#Rotatable Bonds: 9

Polar Surface Area: 150.23

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.09

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: -9.07

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: 0.51

References

1. Barinka C, Novakova Z, Hin N, Bím D, Ferraris DV, Duvall B, Kabarriti G, Tsukamoto R, Budesinsky M, Motlova L, Rojas C, Slusher BS, Rokob TA, Rulíšek L, Tsukamoto T..  (2019)  Structural and computational basis for potent inhibition of glutamate carboxypeptidase II by carbamate-based inhibitors.,  27  (2): [PMID:30552009] [10.1016/j.bmc.2018.11.022]

Source

Source(1):

• Scientific Literature