(S)-3-(1H-Indol-3-yl)-2-[(2-phenyl-cyclopropanecarbonyl)-amino]-propionic acid

ID: ALA418898

Chembl Id: CHEMBL418898

PubChem CID: 9863132

Max Phase: Preclinical

Molecular Formula: C21H20N2O3

Molecular Weight: 348.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: IRL-1722 | IRL-1722|CHEMBL418898|BDBM50287880|(S)-3-(1H-Indol-3-yl)-2-[(2-phenyl-cyclopropanecarbonyl)-amino]-propionic acid

Canonical SMILES:  O=C(N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)C1CC1c1ccccc1

Standard InChI:  InChI=1S/C21H20N2O3/c24-20(17-11-16(17)13-6-2-1-3-7-13)23-19(21(25)26)10-14-12-22-18-9-5-4-8-15(14)18/h1-9,12,16-17,19,22H,10-11H2,(H,23,24)(H,25,26)/t16?,17?,19-/m0/s1

Standard InChI Key:  DRPGADQFIJJWNZ-TVPLGVNVSA-N

Alternative Forms

1. Parent:

   

   ALA418898

   (S)-3-(1H-Indol-3-yl)-2-[(2-phenyl-cyclopropanecarbonyl)-amino]-propionic 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: 348.40

Molecular Weight (Monoisotopic): 348.1474

AlogP: 3.08

#Rotatable Bonds: 6

Polar Surface Area: 82.19

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 0.09

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: -0.23

References

1. Fruh T, Saika H, Svensson L, Pitterna T, Sakaki J, Okada T, Urade Y, Oda K, Fujitani Y, Takimoto M, Yamamura T, Inui T, Makatani M, Umemura I, Teno N, Toh H, Hayakawa K, Murata T.  (1996)  IRL 2500: A potent ETB selective endothelin antagonist,  6  (19): [10.1016/0960-894X(96)00421-0]

Source

Source(1):

• Scientific Literature