1-benzoyl-2-(hydroxymethyl)-1H-indole-3-carboxylic acid

ID: ALA5283862

Max Phase: Preclinical

Molecular Formula: C17H13NO4

Molecular Weight: 295.29

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(CO)n(C(=O)c2ccccc2)c2ccccc12

Standard InChI:  InChI=1S/C17H13NO4/c19-10-14-15(17(21)22)12-8-4-5-9-13(12)18(14)16(20)11-6-2-1-3-7-11/h1-9,19H,10H2,(H,21,22)

Standard InChI Key:  DLSFPSBBLHNWHS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.9639    1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    1.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2336    0.0248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    0.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2530    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    2.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5530    0.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759    1.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.9465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837   -1.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881   -1.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4490   -1.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055   -2.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011   -2.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1597   -2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2675   -0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9759    0.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  4  5  1  0
  6  5  1  0
  3  7  1  0
  7  6  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 20 15  2  0
 19 20  1  0
 21  4  1  0
 22 21  2  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283862

   ---

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: 295.29

Molecular Weight (Monoisotopic): 295.0845

AlogP: 2.52

#Rotatable Bonds: 3

Polar Surface Area: 79.53

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: -1.23

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -0.32

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