3-(3,4-dioxo-2-(pentan-3-ylamino)cyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide

ID: ALA218964

Chembl Id: CHEMBL218964

Max Phase: Preclinical

Molecular Formula: C18H23N3O4

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O

Standard InChI:  InChI=1S/C18H23N3O4/c1-5-10(6-2)19-13-14(17(24)16(13)23)20-12-9-7-8-11(15(12)22)18(25)21(3)4/h7-10,19-20,22H,5-6H2,1-4H3

Standard InChI Key:  RZXVFVRPSNXVEC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA218964

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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: 345.40

Molecular Weight (Monoisotopic): 345.1689

AlogP: 2.03

#Rotatable Bonds: 7

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: 2.37

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.52

Np Likeness Score: -0.74

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