1-(3-Benzoylsulfanyl-2-methyl-propionyl)-2,3-dihydro-1H-indole-2-carboxylic acid

ID: ALA3350269

PubChem CID: 6713089

Max Phase: Preclinical

Molecular Formula: C20H19NO4S

Molecular Weight: 369.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](CSC(=O)c1ccccc1)C(=O)N1c2ccccc2C[C@@H]1C(=O)O

Standard InChI:  InChI=1S/C20H19NO4S/c1-13(12-26-20(25)14-7-3-2-4-8-14)18(22)21-16-10-6-5-9-15(16)11-17(21)19(23)24/h2-10,13,17H,11-12H2,1H3,(H,23,24)/t13-,17+/m0/s1

Standard InChI Key:  YTQUHORAJYMUKY-SUMWQHHRSA-N

Molfile:  

     RDKit          2D

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   -3.0820    1.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7649   -0.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4594    1.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934    1.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    1.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4709    1.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240   -0.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762   -0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6357   -0.5051    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4422   -0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589   -0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8423    0.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9298    0.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066   -0.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8537    1.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1424    0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1481    2.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590   -1.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2008   -1.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5051   -0.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8311    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8311    1.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2225   -0.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5223   -1.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283   -1.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  2  6  1  6
  7  4  2  0
  8 10  1  0
  9  3  1  0
 10 12  1  0
 11  3  2  0
 12  9  1  0
 13  6  2  0
 14  8  2  0
 15  8  1  0
 16  6  1  0
 17  4  1  0
 18  7  1  0
  9 19  1  6
 20 15  2  0
 21 15  1  0
 22 17  2  0
 23 18  2  0
 24 21  2  0
 25 20  1  0
 26 25  2  0
  5  7  1  0
 23 22  1  0
 24 26  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA3350269

   ---

2. Parent:

   

   ALA3350269

   (2R)-1-[(2R)-3-benzoylsulfanyl-2-methylpropanoyl]-2,3-dihydroindole-2-carboxylic 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: 369.44

Molecular Weight (Monoisotopic): 369.1035

AlogP: 3.24

#Rotatable Bonds: 5

Polar Surface Area: 74.68

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: ┄

CX LogP: 3.91

CX LogD: 0.56

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.88

Np Likeness Score: -0.38

References

1. Kim DH, Guinosso CJ, Buzby GC, Herbst DR, McCaully RJ, Wicks TC, Wendt RL..  (1983)  (Mercaptopropanoyl)indoline-2-carboxylic acids and related compounds as potent angiotensin converting enzyme inhibitors and antihypertensive agents.,  26  (3): [PMID:6298429] [10.1021/jm00357a014]

2. Kim DH, Guinosso CJ, Buzby GC, Herbst DR, McCaully RJ, Wicks TC, Wendt RL..  (1983)  (Mercaptopropanoyl)indoline-2-carboxylic acids and related compounds as potent angiotensin converting enzyme inhibitors and antihypertensive agents.,  26  (3): [PMID:6298429] [10.1021/jm00357a014]

Source

Source(1):

• Scientific Literature