ID: ALA463526

Max Phase: Preclinical

Molecular Formula: C20H22O4

Molecular Weight: 326.39

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-16743
Synonyms from Alternative Forms(1):

Canonical SMILES:  C/C=C/c1cc(OC)c2c(c1)[C@H](C)[C@@H](c1ccc(O)c(OC)c1)O2

Standard InChI:  InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m0/s1

Standard InChI Key:  ITDOFWOJEDZPCF-FNINDUDTSA-N

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

Properties

Molecular Weight: 326.39

Molecular Weight (Monoisotopic): 326.1518

AlogP: 4.68

#Rotatable Bonds: 4

Polar Surface Area: 47.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.91

CX Basic pKa:

CX LogP: 4.51

CX LogD: 4.51

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: 1.79

References

1. Le Quesne PW, Larrahondo JE, Raffauf RF..  (1980)  Antitumor plants. X. Constituents of Nectandra rigida.,  43  (3): [PMID:7400821] [10.1021/np50009a006]

2. Coy ED, Cuca LE, Sefkow M..  (2009)  COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.,  19  (24): [PMID:19880317] [10.1016/j.bmcl.2009.10.069]

3. PubChem BioAssay data set, 

4. Habash M, Taha MO..  (2011)  Ligand-based modelling followed by synthetic exploration unveil novel glycogen phosphorylase inhibitory leads.,  19  (16): [PMID:21788139] [10.1016/j.bmc.2011.06.086]

5. Tsai WJ, Shen CC, Tsai TH, Lin LC..  (2014)  Lignans from the aerial parts of Saururus chinensis: isolation, structural characterization, and their effects on platelet aggregation.,  77  (1): [PMID:24387347] [10.1021/np400772h]

6. Park JY, Hwan Lim S, Ram Kim B, Jae Jeong H, Kwon HJ, Song GY, Bae Ryu Y, Song Lee W..  (2017)  Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of Myristica fragrans.,  27  (14): [PMID:28551100] [10.1016/j.bmcl.2017.05.055]

7. Bernal FA,Gerhards M,Kaiser M,Wünsch B,Schmidt TJ.  (2020)  (±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis.,  205  [PMID:32745819] [10.1016/j.ejmech.2020.112493]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays