ROLUPERIDONE

ID: ALA4297605

Cas Number: 359625-79-9

PubChem CID: 9799284

Product Number: C176252, Order Now?

Max Phase: Phase

Molecular Formula: C22H23FN2O2

Molecular Weight: 366.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Roluperidone | FMI | MIN-101 FREE BASE | Roluperidone|359625-79-9|CYR-101|MIN-101|2-((1-(2-(4-fluorophenyl)-2-oxoethyl)piperidin-4-yl)methyl)isoindolin-1-one|MIN-101 FREE BASE|4P31I0M3BF|Roluperidone (USAN)|ROLUPERIDONE [USAN]|1H-Isoindol-1-one, 2-((1-(2-(4-fluorophenyl)-2-oxoethyl)-4-piperidinyl)methyl)-2,3-dihydro-|2-({1-[2-(4-fluorophenyl)-2-oxoethyl]piperidin-4-yl}methyl)-2,3-dihydro-1H-isoindol-1-one|UNII-4P31I0M3BF|Roluperidon|CYR-101(Roluperidone)|Roluperidone; CYR-101|ROLUPERIDONE [INN]|Show More⌵

Synonyms from Alternative Forms(5): Min-101 | Roluperidone hydrochloride | CYR-101 | CYR-101 HYDROCHLORIDE DIHYDRATE | MT-210

Canonical SMILES:  O=C(CN1CCC(CN2Cc3ccccc3C2=O)CC1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C22H23FN2O2/c23-19-7-5-17(6-8-19)21(26)15-24-11-9-16(10-12-24)13-25-14-18-3-1-2-4-20(18)22(25)27/h1-8,16H,9-15H2

Standard InChI Key:  RNRYULFRLCBRQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -5.3243   -0.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368    0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5618    0.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9743   -0.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5618   -1.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368   -1.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4311    0.5850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5174   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3696    1.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7139    0.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    0.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2850    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078   -0.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -0.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -0.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733    0.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5616   -0.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566   -0.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992   -1.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -1.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266   -1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7592   -1.8251    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  1  6  1  0
  7  8  1  0
  7  9  1  0
  1  9  1  0
  8  2  1  0
  8 10  2  0
  7 11  1  0
 11 12  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 17  1  0
 13 12  1  0
 12 14  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 22 26  2  0
 22 21  1  0
 21 23  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4297605

   Roluperidone

2. Alternative Forms:

   

   ALA4297605

   ROLUPERIDONE HYDROCHLORIDE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 366.44

Molecular Weight (Monoisotopic): 366.1744

AlogP: 3.38

#Rotatable Bonds: 5

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.45

CX LogP: 2.88

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -1.22

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Unpublished dataset, 

3. Fallica AN, Ciaffaglione V, Modica MN, Pittalà V, Salerno L, Amata E, Marrazzo A, Romeo G, Intagliata S..  (2022)  Structure-activity relationships of mixed σ₁R/σ₂R ligands with antiproliferative and anticancer effects.,  73  [PMID:36202063] [10.1016/j.bmc.2022.117032]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names