(4aR,4a1R,5aS,8aS,8a1S,15aS)-10,11-dimethoxy-14-oxo-2,4a,4a1,5,5a,6,7,8,8a1,14,15,15a-dodecahydro-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-6-ium

ID: ALA501756

Chembl Id: CHEMBL501756

Cas Number: 357-57-3

PubChem CID: 442021

Product Number: B113642

Max Phase: Unknown

Molecular Formula: C23H26N2O4

Molecular Weight: 394.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 10,11-dimethoxystrychnine | 2,3-dimethoxystrychnine | Brucinum | NSC-757797 | BRUCINE|357-57-3|10,11-Dimethoxystrychnine|Brucinum|2,3-Dimethoxystrychnine|(-)-Brucine|2,3-Dimethoxystrychnidin-10-one|l-Brucine|Brucine, Anhydrous|Strychnidin-10-one, 2,3-dimethoxy-|10,11-Dimethystrychnine|Brucina|Brucin|63428-84-2|6NG17YCK6H|Brucine alkaloid|CHEBI:3193|DTXSID2024662|NSC-757797|Bruzin|2,3-Dimethoxy-strychnine|RCRA waste number P018|145428-94-0|Strychnine, 2,3-dimethoxy-|DTXCID204662|Brucin [German]|BShow More⌵

Synonyms from Alternative Forms(6): Brucine sulfate | 10,11-dimethoxystrychnine sulfate | Brucine sulfate anhydrous | Brucine sulphate | Brucine sulphate anhydrous | NSC-463

Canonical SMILES:  COc1cc2c(cc1OC)[C@@]13CCN4CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@H]43

Standard InChI:  InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1

Standard InChI Key:  RRKTZKIUPZVBMF-IBTVXLQLSA-N

Alternative Forms

1. Parent:

   

   ALA501756

   BRUCINE

2. Alternative Forms:

   

   ALA501756

   BRUCINE SULFATE

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: 394.47

Molecular Weight (Monoisotopic): 394.1893

AlogP: 2.11

#Rotatable Bonds: 2

Polar Surface Area: 51.24

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.85

CX LogP: 0.61

CX LogD: -0.85

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: 2.77

References

1. Gharagozloo P, Lazareno S, Popham A, Birdsall NJ..  (1999)  Allosteric interactions of quaternary strychnine and brucine derivatives with muscarinic acetylcholine receptors.,  42  (3): [PMID:9986715] [10.1021/jm970799y]

2. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Fu Y, Zhang Y, He H, Hou L, Di Y, Li S, Luo X, Hao X..  (2012)  Strynuxlines A and B, alkaloids with an unprecedented carbon skeleton from Strychnos nux-vomica.,  75  (11): [PMID:23088673] [10.1021/np300339r]

6. Daval SB, Valant C, Bonnet D, Kellenberger E, Hibert M, Galzi JL, Ilien B..  (2012)  Fluorescent derivatives of AC-42 to probe bitopic orthosteric/allosteric binding mechanisms on muscarinic M1 receptors.,  55  (5): [PMID:22329602] [10.1021/jm201348t]

7. PubChem BioAssay data set, 

8. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

9. PubChem BioAssay data set, 

10.  (2015)  Bitter taste receptors, 

11. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]

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

13. Lee S, Sperry J..  (2022)  Isolation and biological activity of azocine and azocane alkaloids.,  54  [PMID:34923389] [10.1016/j.bmc.2021.116560]

14. Phull MS, Jadav SS, Gundla R, Mainkar PS..  (2021)  A perspective on medicinal chemistry approaches towards adenomatous polyposis coli and Wnt signal based colorectal cancer inhibitors.,  212  [PMID:33445154] [10.1016/j.ejmech.2020.113149]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• IMI-CARE SARS-CoV-2 Data