ID: ALA301226

Max Phase: Preclinical

Molecular Formula: C28H21NO8

Molecular Weight: 499.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(-c2c3c4cc(OC)c(O)cc4oc(=O)c3n3ccc4cc(O)c(OC)cc4c23)cc1O

Standard InChI:  InChI=1S/C28H21NO8/c1-34-20-5-4-14(9-17(20)30)24-25-16-11-23(36-3)19(32)12-21(16)37-28(33)27(25)29-7-6-13-8-18(31)22(35-2)10-15(13)26(24)29/h4-12,30-32H,1-3H3

Standard InChI Key:  POCZBHBFCIWCCV-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: 499.48

Molecular Weight (Monoisotopic): 499.1267

AlogP: 5.16

#Rotatable Bonds: 4

Polar Surface Area: 123.00

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.94

CX Basic pKa:

CX LogP: 3.73

CX LogD: 3.62

Aromatic Rings: 6

Heavy Atoms: 37

QED Weighted: 0.28

Np Likeness Score: 0.91

References

1. Reddy MV, Rao MR, Rhodes D, Hansen MS, Rubins K, Bushman FD, Venkateswarlu Y, Faulkner DJ..  (1999)  Lamellarin alpha 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture.,  42  (11): [PMID:10354398] [10.1021/jm9806650]

2. Yoshida K, Itoyama R, Yamahira M, Tanaka J, Loaëc N, Lozach O, Durieu E, Fukuda T, Ishibashi F, Meijer L, Iwao M..  (2013)  Synthesis, resolution, and biological evaluation of atropisomeric (aR)- and (aS)-16-methyllamellarins N: unique effects of the axial chirality on the selectivity of protein kinases inhibition.,  56  (18): [PMID:23981088] [10.1021/jm400719y]

3. Pla D, Albericio F, Alvarez M.  (2011)  Progress on lamellarins,  2  (8): [10.1039/C1MD00003A]

4. Fukuda T, Umeki T, Tokushima K, Xiang G, Yoshida Y, Ishibashi F, Oku Y, Nishiya N, Uehara Y, Iwao M..  (2017)  Design, synthesis, and evaluation of A-ring-modified lamellarin N analogues as noncovalent inhibitors of the EGFR T790M/L858R mutant.,  25  (24): [PMID:29133033] [10.1016/j.bmc.2017.10.030]

5. Salehian F, Nadri H, Jalili-Baleh L, Youseftabar-Miri L, Abbas Bukhari SN, Foroumadi A, Tüylü Küçükkilinç T, Sharifzadeh M, Khoobi M..  (2021)  A review: Biologically active 3,4-heterocycle-fused coumarins.,  212  [PMID:33276991] [10.1016/j.ejmech.2020.113034]

Source

Source(1):

• Scientific Literature