L-gamma-methyleneglutamine

ID: ALA5283079

Max Phase: Preclinical

Molecular Formula: C6H10N2O3

Molecular Weight: 158.16

Names and Identifiers

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

Standard InChI:  InChI=1S/C6H10N2O3/c1-3(5(8)9)2-4(7)6(10)11/h4H,1-2,7H2,(H2,8,9)(H,10,11)/t4-/m0/s1

Standard InChI Key:  CEVQXWMPODOBRM-BYPYZUCNSA-N

Molfile:  

 
     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -2.1439   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    1.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -1.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1439   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  1
  8 10  2  0
  8 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283079

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 158.16

Molecular Weight (Monoisotopic): 158.0691

AlogP: -1.17

#Rotatable Bonds: 4

Polar Surface Area: 106.41

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.18

CX Basic pKa: 9.26

CX LogP: -3.55

CX LogD: -3.56

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.45

Np Likeness Score: 1.13

References

1. Khan MIH, Mahdi F, Penfornis P, Akins NS, Hossain MI, Kim SJ, Sulochana SP, Adam AT, Tran TD, Tan C, Paolo Claudio P, Paris JJ, Le HV..  (2023)  Synthesis and biological evaluation of tert-butyl ester and ethyl ester prodrugs of L-γ-methyleneglutamic acid amides for cancer.,  78  [PMID:36603398] [10.1016/j.bmc.2022.117137]

Source

Source(1):

• Scientific Literature