lacinartin

ID: ALA567517

Chembl Id: CHEMBL567517

PubChem CID: 5324625

Max Phase: Preclinical

Molecular Formula: C15H16O4

Molecular Weight: 260.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lacinartin | lacinartin|8-methoxy-7-(3-methylbut-2-enoxy)chromen-2-one|CHEMBL567517|BDBM50491068|InChI=1/C15H16O4/c1-10(2)8-9-18-12-6-4-11-5-7-13(16)19-14(11)15(12)17-3/h4-8H,9H2,1-3H

Canonical SMILES:  COc1c(OCC=C(C)C)ccc2ccc(=O)oc12

Standard InChI:  InChI=1S/C15H16O4/c1-10(2)8-9-18-12-6-4-11-5-7-13(16)19-14(11)15(12)17-3/h4-8H,9H2,1-3H3

Standard InChI Key:  KBHJUIRMCYXTBK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA567517

   LACINARTIN

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: 260.29

Molecular Weight (Monoisotopic): 260.1049

AlogP: 3.15

#Rotatable Bonds: 4

Polar Surface Area: 48.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.83

CX LogD: 2.83

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 1.38

References

1. Genovese S, Epifano F, Curini M, Dudra-Jastrzebska M, Luszczki JJ..  (2009)  Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.,  19  (18): [PMID:19679472] [10.1016/j.bmcl.2009.07.110]

2. Bruyère C, Genovese S, Lallemand B, Ionescu-Motatu A, Curini M, Kiss R, Epifano F..  (2011)  Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.,  21  (14): [PMID:21696954] [10.1016/j.bmcl.2011.05.089]

3. Epifano F, Genovese S, James Squires E, Gray MA..  (2012)  Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.,  22  (9): [PMID:22472691] [10.1016/j.bmcl.2012.03.057]

4. Patil PO, Bari SB, Firke SD, Deshmukh PK, Donda ST, Patil DA..  (2013)  A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease.,  21  (9): [PMID:23517722] [10.1016/j.bmc.2013.02.017]

5. Fiorito S, Epifano F, Preziuso F, Cacciatore I, di Stefano A, Taddeo VA, de Medina P, Genovese S..  (2018)  Natural oxyprenylated coumarins are modulators of melanogenesis.,  152  [PMID:29730190] [10.1016/j.ejmech.2018.04.051]

6. Baek SC, Kang MG, Park JE, Lee JP, Lee H, Ryu HW, Park CM, Park D, Cho ML, Oh SR, Kim H..  (2019)  Osthenol, a prenylated coumarin, as a monoamine oxidase A inhibitor with high selectivity.,  29  (6): [PMID:30686752] [10.1016/j.bmcl.2019.01.016]

Source

Source(1):

• Scientific Literature