ID: ALA470649

Max Phase: Preclinical

Molecular Formula: C10H10O5

Molecular Weight: 210.19

Molecule Type: Small molecule

Representations

Synonyms (2): Methyl Beta-Orcinol Carboxylate | Methyl Haematommate
Synonyms from Alternative Forms(2):

Canonical SMILES:  COC(=O)c1c(C)cc(O)c(C=O)c1O

Standard InChI:  InChI=1S/C10H10O5/c1-5-3-7(12)6(4-11)9(13)8(5)10(14)15-2/h3-4,12-13H,1-2H3

Standard InChI Key:  PXFMUVDLJWXOQM-UHFFFAOYSA-N

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

Properties

Molecular Weight: 210.19

Molecular Weight (Monoisotopic): 210.0528

AlogP: 1.01

#Rotatable Bonds: 2

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.72

CX Basic pKa:

CX LogP: 3.55

CX LogD: 3.38

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.56

Np Likeness Score: 1.21

References

1. Rojas IS, Lotina-Hennsen B, Mata R..  (2000)  Effect of lichen metabolites on thylakoid electron transport and photophosphorylation in isolated spinach chloroplasts.,  63  (10): [PMID:11076561] [10.1021/np0001326]

2. Seo C, Sohn JH, Ahn JS, Yim JH, Lee HK, Oh H..  (2009)  Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum.,  19  (10): [PMID:19362837] [10.1016/j.bmcl.2009.03.108]

3. Millot M, Tomasi S, Studzinska E, Rouaud I, Boustie J..  (2009)  Cytotoxic constituents of the lichen Diploicia canescens.,  72  (12): [PMID:19919064] [10.1021/np9003728]

4. PubChem BioAssay data set, 

5. Goel M, Dureja P, Rani A, Uniyal PL, Laatsch H..  (2011)  Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl.,  59  (6): [PMID:21351753] [10.1021/jf1049613]

6. Carpentier C, Queiroz EF, Marcourt L, Wolfender JL, Azelmat J, Grenier D, Boudreau S, Voyer N..  (2017)  Dibenzofurans and Pseudodepsidones from the Lichen Stereocaulon paschale Collected in Northern Quebec.,  80  (1): [PMID:28079378] [10.1021/acs.jnatprod.6b00831]

7. Carpentier C, Barbeau X, Azelmat J, Vaillancourt K, Grenier D, Lagüe P, Voyer N..  (2018)  Lobaric acid and pseudodepsidones inhibit NF-κB signaling pathway by activation of PPAR-γ.,  26  (22): [PMID:30420328] [10.1016/j.bmc.2018.10.035]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays