2-hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-6-ylium

ID: ALA479291

Chembl Id: CHEMBL479291

PubChem CID: 3738100

Max Phase: Preclinical

Molecular Formula: C16H11NO3

Molecular Weight: 265.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ungeremine | CHEBI:32277|CHEMBL479291|BDBM50358566|5,7-Dioxa-12-azoniapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,11,15(19),16-heptaen-17-olate

Canonical SMILES:  [O-]c1cc2c3c(c1)c1cc4c(cc1c[n+]3CC2)OCO4

Standard InChI:  InChI=1S/C16H11NO3/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17/h3-7H,1-2,8H2

Standard InChI Key:  DFQOXFIPAAMFAU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA479291

   UNGEREMINE

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: 265.27

Molecular Weight (Monoisotopic): 265.0739

AlogP: 1.64

#Rotatable Bonds: 0

Polar Surface Area: 45.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.88

CX Basic pKa:

CX LogP: -1.82

CX LogD: -1.94

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.46

Np Likeness Score: 1.25

References

1. Wang YH, Zhang ZK, Yang FM, Sun QY, He HP, Di YT, Mu SZ, Lu Y, Chang Y, Zheng QT, Ding M, Dong JH, Hao XJ..  (2007)  Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase.,  70  (9): [PMID:17822295] [10.1021/np0702077]

2. Pettit GR, Meng Y, Herald DL, Knight JC, Day JF..  (2005)  Antineoplastic agents. 553. The Texas grasshopper Brachystola magna.,  68  (8): [PMID:16124772] [10.1021/np0402367]

3. Evidente A, Randazzo G, Surico G, Lavermicocca P, Arrigoni O.  (1985)  Degradation of Lycorine by Pseudomonas Species Strain ITM 311,  48  (4): [10.1021/np50040a008]

4. Lamoral-Theys D, Andolfi A, Van Goietsenoven G, Cimmino A, Le Calvé B, Wauthoz N, Mégalizzi V, Gras T, Bruyère C, Dubois J, Mathieu V, Kornienko A, Kiss R, Evidente A..  (2009)  Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: an investigation of structure-activity relationship and mechanistic insight.,  52  (20): [PMID:19788245] [10.1021/jm901031h]

5. Van Goietsenoven G, Andolfi A, Lallemand B, Cimmino A, Lamoral-Theys D, Gras T, Abou-Donia A, Dubois J, Lefranc F, Mathieu V, Kornienko A, Kiss R, Evidente A..  (2010)  Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.,  73  (7): [PMID:20550100] [10.1021/np9008255]

6. Casu L, Cottiglia F, Leonti M, De Logu A, Agus E, Tse-Dinh YC, Lombardo V, Sissi C..  (2011)  Ungeremine effectively targets mammalian as well as bacterial type I and type II topoisomerases.,  21  (23): [PMID:22014547] [10.1016/j.bmcl.2011.09.097]

7. Zee-Cheng RK, Yan SJ, Cheng CC..  (1978)  Antileukemic activity of ungeremine and related compounds. Preparation of analogues of ungeremine by a practical photochemical reaction.,  21  (2): [PMID:621715] [10.1021/jm00200a011]

8. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

9. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature