ID: ALA490329

Max Phase: Preclinical

Molecular Formula: C19H32O4

Molecular Weight: 324.46

Molecule Type: Small molecule

Representations

Synonyms (2): (+)-Protolichesterinic Acid | Protolichesterinic Acid
Synonyms from Alternative Forms(2):

Canonical SMILES:  C=C1C(=O)O[C@@H](CCCCCCCCCCCCC)[C@@H]1C(=O)O

Standard InChI:  InChI=1S/C19H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h16-17H,2-14H2,1H3,(H,20,21)/t16-,17+/m0/s1

Standard InChI Key:  WZYZDHVPSZCEEP-DLBZAZTESA-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: 324.46

Molecular Weight (Monoisotopic): 324.2301

AlogP: 4.87

#Rotatable Bonds: 13

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.24

CX Basic pKa:

CX LogP: 6.04

CX LogD: 3.04

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.30

Np Likeness Score: 1.19

References

1. Kumar KC, Müller K..  (1999)  Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism.,  62  (6): [PMID:10395494] [10.1021/np9803777]

2. Kumar KC, Müller K..  (1999)  Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth.,  62  (6): [PMID:10395495] [10.1021/np980378z]

3. Pengsuparp T, Cai L, Constant H, Fong HH, Lin LZ, Kinghorn AD, Pezzuto JM, Cordell GA, Ingolfsdóttir K, Wagner H..  (1995)  Mechanistic evaluation of new plant-derived compounds that inhibit HIV-1 reverse transcriptase.,  58  (7): [PMID:7561895] [10.1021/np50121a006]

4. Le Lamer AC, Authier H, Rouaud I, Coste A, Boustie J, Pipy B, Gouault N..  (2014)  Protolichesterinic acid derivatives: α-methylene-γ-lactones as potent dual activators of PPARγ and Nrf2 transcriptional factors.,  24  (16): [PMID:25027935] [10.1016/j.bmcl.2014.06.062]

Source

Source(1):

• Scientific Literature