3-Amino-4-methoxy-benzenesulfonic acid 3,4,5-trimethoxy-phenyl ester

ID: ALA423439

PubChem CID: 9820655

Max Phase: Preclinical

Molecular Formula: C16H19NO7S

Molecular Weight: 369.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)Oc2cc(OC)c(OC)c(OC)c2)cc1N

Standard InChI:  InChI=1S/C16H19NO7S/c1-20-13-6-5-11(9-12(13)17)25(18,19)24-10-7-14(21-2)16(23-4)15(8-10)22-3/h5-9H,17H2,1-4H3

Standard InChI Key:  ZSVLWJYTWYQJQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.1542   -3.0292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -3.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -2.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4375   -2.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -3.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8875   -5.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -3.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -0.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4667   -5.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  2  0
  4  1  1  0
  5  9  2  0
  6 10  1  0
  7  2  2  0
  8  4  1  0
  9  8  1  0
 10  8  2  0
 11  7  1  0
 12  1  2  0
 13  1  2  0
 14 16  1  0
 15  2  1  0
 16 15  2  0
 17 11  1  0
 18  3  1  0
 19  6  1  0
 20  5  1  0
 21 14  1  0
 22 18  1  0
 23 20  1  0
 24 19  1  0
 25 21  1  0
  5  3  1  0
 11 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA423439

   3-Amino-4-methoxy-benzenesulfonic acid 3,4,5-trimethoxy-phenyl ester

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: 369.40

Molecular Weight (Monoisotopic): 369.0882

AlogP: 2.07

#Rotatable Bonds: 7

Polar Surface Area: 106.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.92

CX LogP: 1.73

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.30

References

1. Gwaltney SL, Imade HM, Barr KJ, Li Q, Gehrke L, Credo RB, Warner RB, Lee JY, Kovar P, Wang J, Nukkala MA, Zielinski NA, Frost D, Ng SC, Sham HL..  (2001)  Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents.,  11  (7): [PMID:11294380] [10.1016/s0960-894x(01)00098-1]

Source

Source(1):

• Scientific Literature