6,9-Dimethyl-3-methylene-3,3a,4,5,9a,9b-hexahydro-azuleno[4,5-b]furan-2,7-dione

ID: ALA441260

Chembl Id: CHEMBL441260

Cas Number: 36150-07-9

PubChem CID: 73440

Max Phase: Preclinical

Molecular Formula: C15H16O3

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dehydroleucodin | Dehydroleucodine | Dehydroleucodine|Dehydroleucodin|36150-07-9|CHEMBL441260|NSC 180034|SCHEMBL4998391|Dehydroleucodine, >=98% (HPLC)|BDBM50318392|AKOS040762600|NCGC00485131-01|(3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione|Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-6,9-dimethyl-3-methylene-, (3aS-(3aalpha,9aalpha,9bbeta))-|HY-122295|CS-0083475|6,9-Dimethyl-3-methylene-3,3a,4,5,9a,9b-hexahydro-azuleno[4,5-b]furan-2,7-Show More⌵

Canonical SMILES:  C=C1C(=O)O[C@@H]2[C@H]3C(C)=CC(=O)C3=C(C)CC[C@@H]12

Standard InChI:  InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1

Standard InChI Key:  SKNVIAFTENCNGB-BPNCWPANSA-N

Alternative Forms

1. Parent:

   

   ALA441260

   DEHYDROLEUCODIN

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: 244.29

Molecular Weight (Monoisotopic): 244.1099

AlogP: 2.34

#Rotatable Bonds: ┄

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: 3.09

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. Siedle B, García-Piñeres AJ, Murillo R, Schulte-Mönting J, Castro V, Rüngeler P, Klaas CA, Da Costa FB, Kisiel W, Merfort I..  (2004)  Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB.,  47  (24): [PMID:15537359] [10.1021/jm049937r]

3. Wagner S, Hofmann A, Siedle B, Terfloth L, Merfort I, Gasteiger J..  (2006)  Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.,  49  (7): [PMID:16570920] [10.1021/jm051125n]

4. 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]

5. Guardia T, Guzman JA, Pestchanker MJ, Guerreiro E, Giordano OS..  (1994)  Mucus synthesis and sulfhydryl groups in cytoprotection mediated by dehydroleucodine, a sesquiterpene lactone.,  57  (4): [PMID:8021651] [10.1021/np50106a010]

6. 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]

7. Ordóñez PE, Sharma KK, Bystrom LM, Alas MA, Enriquez RG, Malagón O, Jones DE, Guzman ML, Compadre CM..  (2016)  Dehydroleucodine, a Sesquiterpene Lactone from Gynoxys verrucosa, Demonstrates Cytotoxic Activity against Human Leukemia Cells.,  79  (4): [PMID:27057812] [10.1021/acs.jnatprod.5b00383]

8. Dürr L, Reinhardt JK, Dobrzyński M, Hell T, Smieško M, Pertz O, Hamburger M, Garo E..  (2022)  A Dimerosesquiterpene and Sesquiterpene Lactones from Artemisia argyi Inhibiting Oncogenic PI3K/AKT Signaling in Melanoma Cells.,  85  (11.0): [PMID:36351173] [10.1021/acs.jnatprod.2c00471]

Source

Source(1):

• Scientific Literature