2-(hydroxymethyl)-1-(4-methylbenzenesulfonyl)-1H-indole-3-carboxylic acid

ID: ALA5282200

Max Phase: Preclinical

Molecular Formula: C17H15NO5S

Molecular Weight: 345.38

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)n2c(CO)c(C(=O)O)c3ccccc32)cc1

Standard InChI:  InChI=1S/C17H15NO5S/c1-11-6-8-12(9-7-11)24(22,23)18-14-5-3-2-4-13(14)16(17(20)21)15(18)10-19/h2-9,19H,10H2,1H3,(H,20,21)

Standard InChI Key:  ZCQLIUTYPMTSHL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.9636    1.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9756    0.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674    0.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471    0.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    0.2240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -0.5639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -1.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528    0.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529    1.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192    2.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285    2.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    2.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    1.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433    1.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739   -0.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895   -1.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    1.5807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -2.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2051   -2.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8918   -0.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  5  1  0
  8  9  1  0
 10  8  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 14 10  1  0
  4 14  2  0
 14 15  1  0
 15  1  2  0
  6 16  2  0
  6 17  2  0
  9 18  1  0
 19  7  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
  7 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282200

   ---

Molecule Features

Natural Product: No

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: 345.38

Molecular Weight (Monoisotopic): 345.0671

AlogP: 2.38

#Rotatable Bonds: 4

Polar Surface Area: 96.60

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.44

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: -1.07

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.76

Np Likeness Score: -0.74

References

1. Danilenko AV, Volov AN, Volov NA, Platonova YB, Savilov SV..  (2023)  Design, synthesis and biological evaluation of novel indole-3-carboxylic acid derivatives with antihypertensive activity.,  90  [PMID:37236375] [10.1016/j.bmcl.2023.129349]

Source

Source(1):

• Scientific Literature