3,6-dimethyl-5-hydroxymethylpyrazin-2-methyl-beta-D-glucuronide

ID: ALA3752942

PubChem CID: 127036455

Max Phase: Preclinical

Molecular Formula: C14H20N2O8

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(CO[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)c(C)nc1CO

Standard InChI:  InChI=1S/C14H20N2O8/c1-5-7(3-17)15-6(2)8(16-5)4-23-14-11(20)9(18)10(19)12(24-14)13(21)22/h9-12,14,17-20H,3-4H2,1-2H3,(H,21,22)/t9-,10-,11+,12-,14+/m0/s1

Standard InChI Key:  DXCZOYCFPGJFET-BYNIDDHOSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    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
   -2.5951    3.0039    0.0000 O   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
   -3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915    3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924    6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924    7.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7928    3.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8542    5.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5307    5.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8312    3.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7949    1.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  2  0
  4  5  1  0
  5  6  2  0
  3  6  1  0
  6  7  1  0
  2  8  1  0
  9 10  1  0
  5  9  1  0
 11 12  1  0
  1 11  1  0
 13 10  1  6
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  6
 15 20  1  6
 18 21  1  1
 16 22  1  1
 20 23  2  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3752942

   ---

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: 344.32

Molecular Weight (Monoisotopic): 344.1220

AlogP: -2.01

#Rotatable Bonds: 5

Polar Surface Area: 162.46

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.91

CX Basic pKa: 1.53

CX LogP: -3.02

CX LogD: -6.51

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.40

Np Likeness Score: 1.00

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