6,8a-Dimethyl-3-methylene-3a,4,5,7,7a,8a,8b,8c-octahydro-3H-1,8-dioxa-cyclopenta[h]cyclopropa[a]azulen-2-one (Ludartin)

ID: ALA1097764

Chembl Id: CHEMBL1097764

PubChem CID: 14355826

Max Phase: Preclinical

Molecular Formula: C15H18O3

Molecular Weight: 246.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ludartin | Ludartin|CHEMBL1097764|BDBM50318394|6,8a-Dimethyl-3-methylene-3a,4,5,7,7a,8a,8b,8c-octahydro-3H-1,8-dioxa-cyclopenta[h]cyclopropa[a]azulen-2-one (Ludartin)

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CCC(C)=C1C[C@H]3O[C@@]3(C)[C@@H]12

Standard InChI:  InChI=1S/C15H18O3/c1-7-4-5-9-8(2)14(16)17-13(9)12-10(7)6-11-15(12,3)18-11/h9,11-13H,2,4-6H2,1,3H3/t9-,11+,12-,13-,15+/m0/s1

Standard InChI Key:  QXJYIGSXUBOSID-JZEMPJKHSA-N

Alternative Forms

1. Parent:

   

   ALA1097764

   LUDARTIN

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: 246.31

Molecular Weight (Monoisotopic): 246.1256

AlogP: 2.37

#Rotatable Bonds: ┄

Polar Surface Area: 38.83

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.28

Np Likeness Score: 3.78

References

1. Giordano OS, Pestchanker MJ, Guerreiro E, Saad JR, Enriz RD, Rodríguez AM, Jáuregui EA, Guzmán J, María AO, Wendel GH..  (1992)  Structure-activity relationship in the gastric cytoprotective effect of several sesquiterpene lactones.,  35  (13): [PMID:1619619] [10.1021/jm00091a013]

2. Giordano OS, Guerreiro E, Pestchanker MJ, Guzman J, Pastor D, Guardia T..  (1990)  The gastric cytoprotective effect of several sesquiterpene lactones.,  53  (4): [PMID:2095374] [10.1021/np50070a004]

3. Muftuoglu Y, Mustata G..  (2010)  Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19).,  20  (10): [PMID:20413308] [10.1016/j.bmcl.2010.03.113]

4. Lone SH, Bhat KA, Shakeel-u-Rehman, Majeed R, Hamid A, Khuroo MA..  (2013)  Synthesis and biological evaluation of amino analogs of Ludartin: potent and selective cytotoxic agents.,  23  (17): [PMID:23886685] [10.1016/j.bmcl.2013.06.068]

5. Lone SH, Bhat KA, Majeed R, Hamid A, Khuroo MA..  (2014)  Click chemistry inspired facile synthesis and bioevaluation of novel triazolyl analogs of Ludartin.,  24  (4): [PMID:24484897] [10.1016/j.bmcl.2014.01.018]

6. Taleghani A, Emami SA, Tayarani-Najaran Z..  (2020)  Artemisia: a promising plant for the treatment of cancer.,  28  (1): [PMID:31784199] [10.1016/j.bmc.2019.115180]

Source

Source(1):

• Scientific Literature