(-)-2-Cyclohexanecarbonyl-2,3,6,7,8,12b-hexahydro-1H-benzo[3,4]azepino[1,2-a]pyrazin-4-one

ID: ALA64979

Chembl Id: CHEMBL64979

Cas Number: 98123-83-2

PubChem CID: 72026

Max Phase: Phase

Molecular Formula: C20H26N2O2

Molecular Weight: 326.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Epsiprantel | BRL 38705 | BRL-38705 | BRL38705 | Epsiprantel|98123-83-2|Cestex|Epsiprantelum|Epsiprantel, (+)-|UNII-0C1SPQ0FSR|0C1SPQ0FSR|WUC74DW9SN|BRL 38705|DTXSID3057858|Epsiprantel, (-)-|Epsiprantelum [Latin]|BRL38705|UNII-WUC74DW9SN|BRL-38705|JU2X6K5BL3|DTXCID0031392|Epsiprantel (INN)|2-(cyclohexanecarbonyl)-1,3,6,7,8,12b-hexahydropyrazino[2,1-a][2]benzazepin-4-one|Epsiprantelum (Latin)|EPSIPRANTEL [INN]|(+)-2-(Cyclohexylcarbonyl)-2,3,6,7,8,12b-hexahydropyrazino(2,1-a)(2)benzazepin-4(1H)-onShow More⌵

Canonical SMILES:  O=C(C1CCCCC1)N1CC(=O)N2CCCc3ccccc3C2C1

Standard InChI:  InChI=1S/C20H26N2O2/c23-19-14-21(20(24)16-8-2-1-3-9-16)13-18-17-11-5-4-7-15(17)10-6-12-22(18)19/h4-5,7,11,16,18H,1-3,6,8-10,12-14H2

Standard InChI Key:  LGUDKOQUWIHXOV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA64979

   EPSIPRANTEL

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: 326.44

Molecular Weight (Monoisotopic): 326.1994

AlogP: 2.93

#Rotatable Bonds: 1

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.87

References

1. Brewer MD, Burgess MN, Dorgan RJ, Elliott RL, Mamalis P, Manger BR, Webster RA..  (1989)  Synthesis and anthelmintic activity of a series of pyrazino[2,1-a][2]benzazepine derivatives.,  32  (9): [PMID:2769679] [10.1021/jm00129a007]

2. Brewer MD, Burgess MN, Dorgan RJ, Elliott RL, Mamalis P, Manger BR, Webster RA..  (1989)  Synthesis and anthelmintic activity of a series of pyrazino[2,1-a][2]benzazepine derivatives.,  32  (9): [PMID:2769679] [10.1021/jm00129a007]

3. Brewer MD, Burgess MN, Dorgan RJ, Elliott RL, Mamalis P, Manger BR, Webster RA..  (1989)  Synthesis and anthelmintic activity of a series of pyrazino[2,1-a][2]benzazepine derivatives.,  32  (9): [PMID:2769679] [10.1021/jm00129a007]

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

5. PubChem BioAssay data set, 

6. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• IMI-CARE SARS-CoV-2 Data