7-Methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline

ID: ALA36654

Chembl Id: CHEMBL36654

Cas Number: 2030-53-7

PubChem CID: 235224

Max Phase: Preclinical

Molecular Formula: C18H17NO2

Molecular Weight: 279.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GNF-Pf-4466 | Aporheine|Remerine|(R)-Roemerine|GNF-PF-4466|Remerin|CHEMBL36654|2030-53-7|(-)-roemerine|15548-23-9|Roemerin|11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene|l-Roemerine|(-)-Aporheine|Remerine (alkaloid)|6,7,7a,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline|SR-01000810842|1-Remerine|(-)-Remerine|ST082313|Oprea1_656488|Oprea1_838512|MLS001208416|SCHEMBL673805|cid_235224|ACon1_001394|DTXSID10866578|CHEBI:173982|HShow More⌵

Canonical SMILES:  CN1CCc2cc3c(c4c2C1Cc1ccccc1-4)OCO3

Standard InChI:  InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3

Standard InChI Key:  JCTYWRARKVGOBK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA36654

   ROEMERINE

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 279.34

Molecular Weight (Monoisotopic): 279.1259

AlogP: 3.17

#Rotatable Bonds: ┄

Polar Surface Area: 21.70

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.43

CX LogP: 3.32

CX LogD: 3.01

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: 1.46

References

1. Miski M, Xing Shen, Cooper R, Gillum AM, Fisher DK, Miller RW, Higgins TJ.  (1995)  Aporphine alkaloids, CD45 protein tyrosine phosphatase inhibitors, from Rollinia ulei,  5  (14): [10.1016/0960-894X(95)00250-W]

2. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Moreno L, Cabedo N, Ivorra MD, Sanz MJ, Castel AL, Carmen Álvarez M, Cortes D..  (2013)  3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor.,  23  (17): [PMID:23886690] [10.1016/j.bmcl.2013.06.078]

6. Pathak A, Rohilla A, Gupta T, Akhtar MJ, Haider MR, Sharma K, Haider K, Yar MS..  (2018)  DYRK1A kinase inhibition with emphasis on neurodegeneration: A comprehensive evolution story-cum-perspective.,  158  [PMID:30243157] [10.1016/j.ejmech.2018.08.093]

Source

Source(3):

• Scientific Literature
• Novartis Malaria Screening
• PubChem BioAssays