2-acetamido-3-((5-(hydroxymethyl)-3,6-dimethylpyrazin-2-yl)methylthio)propanoic acid

ID: ALA3752212

PubChem CID: 102340571

Max Phase: Preclinical

Molecular Formula: C13H19N3O4S

Molecular Weight: 313.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NC(CSCc1nc(C)c(CO)nc1C)C(=O)O

Standard InChI:  InChI=1S/C13H19N3O4S/c1-7-10(4-17)14-8(2)11(15-7)5-21-6-12(13(19)20)16-9(3)18/h12,17H,4-6H2,1-3H3,(H,16,18)(H,19,20)

Standard InChI Key:  UAVANFFLSCJVSC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    2.5917   -6.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -7.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524   -5.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956    2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2253   -8.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 10 13  1  0
 13 14  1  0
  9 15  1  0
 16 17  1  0
 12 16  1  0
  7  8  1  0
  6  7  1  0
  3  6  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3752212

   2-Acetamido-3-[[5-(hydroxymethyl)-3,6-dimethylpyrazin-2-yl]methylsulfanyl]propanoic 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: 313.38

Molecular Weight (Monoisotopic): 313.1096

AlogP: 0.41

#Rotatable Bonds: 7

Polar Surface Area: 112.41

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.33

CX Basic pKa: 0.79

CX LogP: -1.69

CX LogD: -5.11

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: -0.32

References

1. Zhu HH, Chen YQ, Cheng D, Li W, Wang TL, Wen HM, Chen L, Liu J..  (2016)  Synthesis and positive inotropic activity evaluation of liguzinediol metabolites.,  26  (3): [PMID:26725025] [10.1016/j.bmcl.2015.12.072]

2. Zhu HH, Chen YQ, Cheng D, Li W, Wang TL, Wen HM, Chen L, Liu J..  (2016)  Synthesis and positive inotropic activity evaluation of liguzinediol metabolites.,  26  (3): [PMID:26725025] [10.1016/j.bmcl.2015.12.072]

Source

Source(1):

• Scientific Literature