(2S,3R,4S)-1-Dibutylcarbamoylmethyl-2-(2,2-dimethyl-pentyl)-4-(7-methoxy-benzo[1,3]dioxol-5-yl)-pyrrolidine-3-carboxylic acid

ID: ALA111612

Chembl Id: CHEMBL111612

Cas Number: 212481-66-8

PubChem CID: 9915028

Max Phase: Preclinical

Molecular Formula: C30H48N2O6

Molecular Weight: 532.72

Molecule Type: Small molecule

Names and Identifiers

Synonyms: A-216546 | ABT-546|A-216546 free base|212481-66-8|PN03VLW8WV|CHEMBL111612|(2S,3R,4S)-1-(2-(dibutylamino)-2-oxoethyl)-2-(2,2-dimethylpentyl)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)pyrrolidine-3-carboxylic acid|(2S,3R,4S)-1-[(dibutylcarbamoyl)methyl]-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-dioxaindan-5-yl)pyrrolidine-3-carboxylic acid|3-Pyrrolidinecarboxylic acid, 1-(2-(dibutylamino)-2-oxoethyl)-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-, (2S,3R,4S)-|UNII-PN03VLW8WV|SCHEMBL795037|BDBShow More⌵

Canonical SMILES:  CCCCN(CCCC)C(=O)CN1C[C@H](c2cc(OC)c3c(c2)OCO3)[C@@H](C(=O)O)[C@@H]1CC(C)(C)CCC

Standard InChI:  InChI=1S/C30H48N2O6/c1-7-10-13-31(14-11-8-2)26(33)19-32-18-22(21-15-24(36-6)28-25(16-21)37-20-38-28)27(29(34)35)23(32)17-30(4,5)12-9-3/h15-16,22-23,27H,7-14,17-20H2,1-6H3,(H,34,35)/t22-,23+,27-/m1/s1

Standard InChI Key:  OAEWNSKRLBVVBV-QSEAXJEQSA-N

Alternative Forms

1. Parent:

   

   ALA111612

   ABT-546

2. Alternative Forms:

   

   ALA111612

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

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: 532.72

Molecular Weight (Monoisotopic): 532.3512

AlogP: 5.54

#Rotatable Bonds: 15

Polar Surface Area: 88.54

Molecular Species: ZWITTERION

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.24

CX Basic pKa: 8.90

CX LogP: 2.84

CX LogD: 2.82

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.32

Np Likeness Score: 0.08

References

1. Liu G, Henry KJ, Szczepankiewicz BG, Winn M, Kozmina NS, Boyd SA, Wasicak J, von Geldern TW, Wu-Wong JR, Chiou WJ, Dixon DB, Nguyen B, Marsh KC, Opgenorth TJ..  (1998)  Pyrrolidine-3-carboxylic acids as endothelin antagonists. 3. Discovery of a potent, 2-nonaryl, highly selective ETA antagonist (A-216546).,  41  (17): [PMID:9703472] [10.1021/jm980217s]

2. Jae HS, Winn M, von Geldern TW, Sorensen BK, Chiou WJ, Nguyen B, Marsh KC, Opgenorth TJ..  (2001)  Pyrrolidine-3-carboxylic acids as endothelin antagonists. 5. Highly selective, potent, and orally active ET(A) antagonists.,  44  (23): [PMID:11689084] [10.1021/jm010237l]

3. SGC Frankfurt.  (2021)  Data for DCP probe ABT-546,  [10.6019/CHEMBL4507258]

Source

Source(2):

• Scientific Literature
• Donated Chemical Probes - SGC Frankfurt