7,9-Dimethyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline

ID: ALA449081

Chembl Id: CHEMBL449081

Cas Number: 548-42-5

PubChem CID: 73484

Max Phase: Preclinical

Molecular Formula: C16H18N2

Molecular Weight: 238.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Agroclavine | Agroclavine|8,9-Didehydro-6,8-dimethylergoline|(-)-agroclavine|548-42-5|Ergoline, 8,9-didehydro-6,8-dimethyl-|(5R,10R)-agroclavine|6,8-Dimethyl-8,9-didehydroergoline|AGROCLAVIN|A8SW57GO7T|CHEBI:2519|CHEMBL449081|NSC93132|(6aR,10aR)-7,9-dimethyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinoline|(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline|CCRIS 2099|Indolo(4,3-fg)quinoline, 4,6,6a,7,8,10a-hexahydro-7,9-dimethyl-|EINECS 208-947-3|NSC 93132|UNII-A8SW57GO7T|BRShow More⌵

Canonical SMILES:  CC1=C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1

Standard InChI:  InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m1/s1

Standard InChI Key:  XJOOMMHNYOJWCZ-UKRRQHHQSA-N

Alternative Forms

1. Parent:

   

   ALA449081

   AGROCLAVINE

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: 238.33

Molecular Weight (Monoisotopic): 238.1470

AlogP: 3.07

#Rotatable Bonds: ┄

Polar Surface Area: 19.03

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.40

CX LogP: 2.78

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.70

Np Likeness Score: 1.52

References

1. Ward JS, Fuller RW, Merritt L, Snoddy HD, Paschal JW, Mason NR, Horng JS..  (1988)  Ergolines as selective 5-HT1 agonists.,  31  (8): [PMID:2456389] [10.1021/jm00403a007]

2. Bruno-Blanch L, Gálvez J, García-Domenech R..  (2003)  Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.,  13  (16): [PMID:12873507] [10.1016/s0960-894x(03)00535-3]

3. Padmanabha R, Shu YZ, Cook LS, Veitch JA, Donovan M, Lowe S, Huang S, Pirnik D, Manly SP..  (1998)  1-Methoxy-agroclavine from Penicillium sp. WC75209, a novel inhibitor of the Lck tyrosine kinase.,  8  (6): [PMID:9871562] [10.1016/s0960-894x(98)00072-9]

4. Bach NJ, Kornfeld EC, Clemens JA, Smalstig EB..  (1980)  Conversion of ergolines to hexahydro- and octahydrobenzo[f]quinolines (depyrroloergolines).,  23  (7): [PMID:7190615] [10.1021/jm00181a021]

5. Tupper DE, Pullar IA, Clemens JA, Fairhurst J, Risius FC, Timms GH, Wedley S..  (1993)  Synthesis and dopamine antagonist activity of 2-thioether derivatives of the ergoline ring system.,  36  (7): [PMID:8096548] [10.1021/jm00059a017]

6. Cheng L, Robbers JE, Floss HG.  (1980)  End-Product Regulation of Ergot Alkaloid Formation in Intact Cells and Protoplasts of Claviceps Species, Strain SD 58,  43  (3): [10.1021/np50009a003]

7. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays