(R)-3-(2-(1-(furan-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide

ID: ALA218115

Chembl Id: CHEMBL218115

PubChem CID: 10150526

Max Phase: Preclinical

Molecular Formula: C20H21N3O5

Molecular Weight: 383.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O)c1ccco1

Standard InChI:  InChI=1S/C20H21N3O5/c1-4-12(14-9-6-10-28-14)21-15-16(19(26)18(15)25)22-13-8-5-7-11(17(13)24)20(27)23(2)3/h5-10,12,21-22,24H,4H2,1-3H3/t12-/m1/s1

Standard InChI Key:  JBJWLRHFBRZPOP-GFCCVEGCSA-N

Alternative Forms

1. Parent:

   

   ALA218115

   (R)-3-(2-(1-(furan-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide

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: 383.40

Molecular Weight (Monoisotopic): 383.1481

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 111.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.02

References

1. Dwyer MP, Yu Y, Chao J, Aki C, Chao J, Biju P, Girijavallabhan V, Rindgen D, Bond R, Mayer-Ezel R, Jakway J, Hipkin RW, Fossetta J, Gonsiorek W, Bian H, Fan X, Terminelli C, Fine J, Lundell D, Merritt JR, Rokosz LL, Kaiser B, Li G, Wang W, Stauffer T, Ozgur L, Baldwin J, Taveras AG..  (2006)  Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist.,  49  (26): [PMID:17181143] [10.1021/jm0609622]

2. Chasák J, Šlachtová V, Urban M, Brulíková L..  (2021)  Squaric acid analogues in medicinal chemistry.,  209  [PMID:33035923] [10.1016/j.ejmech.2020.112872]

Source

Source(1):

• Scientific Literature