Marliolide; (E,4S,5S)-Dihydro-4-hydroxy-5-methyl-3-tetradecylidenefuran-2(3H)-one

ID: ALA4215699

Chembl Id: CHEMBL4215699

PubChem CID: 11301366

Max Phase: Preclinical

Molecular Formula: C19H34O3

Molecular Weight: 310.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCC/C=C1/C(=O)O[C@@H](C)[C@H]1O

Standard InChI:  InChI=1S/C19H34O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17-18(20)16(2)22-19(17)21/h15-16,18,20H,3-14H2,1-2H3/b17-15+/t16-,18+/m0/s1

Standard InChI Key:  KBHLNNQHHPFDSG-DBTFZPMKSA-N

Alternative Forms

1. Parent:

   

   ALA4215699

   (3E,4S,5S)-4-hydroxy-5-methyl-3-tetradecylideneoxolan-2-one

Molecule Features

Natural Product: No

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: 310.48

Molecular Weight (Monoisotopic): 310.2508

AlogP: 4.92

#Rotatable Bonds: 12

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.31

CX Basic pKa: ┄

CX LogP: 6.05

CX LogD: 6.05

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.32

Np Likeness Score: 1.58

References

1. Lee J, Mailar K, Yoo OK, Choi WJ, Keum YS..  (2018)  Marliolide inhibits skin carcinogenesis by activating NRF2/ARE to induce heme oxygenase-1.,  150  [PMID:29525432] [10.1016/j.ejmech.2018.02.068]

2. Ahn S, Basavana Gowda MK, Lee M, Masagalli JN, Mailar K, Choi WJ, Noh M..  (2020)  Novel linked butanolide dimer compounds increase adiponectin production during adipogenesis in human mesenchymal stem cells through peroxisome proliferator-activated receptor γ modulation.,  187  [PMID:31865018] [10.1016/j.ejmech.2019.111969]

Source

Source(1):

• Scientific Literature