2a-[2-(4-Methyl-pyrazin-1-yl)-ethyl]-2a,3,4,5-tetrahydro-1H-benzo[cd]indol-2-one

ID: ALA19215

Chembl Id: CHEMBL19215

Cas Number: 17692-51-2

PubChem CID: 28693

Product Number: M131798

Max Phase: Approved

Molecular Formula: C25H29N3O2

Molecular Weight: 403.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: FI 6337 | FI-6337 | MCE | NSC-755878 | metergoline|17692-51-2|Liserdol|Metergolin|Methergoline|Metergolina|Metergolinum|FI 6337|FI-6337|(+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester|1-Methyl-N-carbobenzyloxydihydro-D-lysergamin|MLS000069437|1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline|1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline|D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline|SMR000059050|(((8-beta)-1,6-Dimethylergolin-8-yl)metShow More⌵

Synonyms from Alternative Forms(1): Metergoline

Trade Names(1): Liserdol

Canonical SMILES:  CN1C[C@H](CNC(=O)OCc2ccccc2)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21

Standard InChI:  InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1

Standard InChI Key:  WZHJKEUHNJHDLS-QTGUNEKASA-N

Alternative Forms

1. Parent:

   

   ALA19215

   METERGOLINE

2. Alternative Forms:

   

   ALA19215

   [11C]-METERGOLINE

Molecule Features

Natural Product: Yes

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: 403.53

Molecular Weight (Monoisotopic): 403.2260

AlogP: 4.06

#Rotatable Bonds: 4

Polar Surface Area: 46.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.22

CX LogP: 3.99

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.71

Np Likeness Score: 0.33

References

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Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• EU-OPENSCREEN dataset