Cyclopiazonic acid

ID: ALA468766

Chembl Id: CHEMBL468766

Max Phase: Preclinical

Molecular Formula: C20H20N2O3

Molecular Weight: 336.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(O)=C1\C(=O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O

Standard InChI:  InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,23H,7H2,1-3H3/b14-9-/t12-,16+,17+/m1/s1

Standard InChI Key:  CNZIQHGDUXRUJS-PTNHGACKSA-N

Alternative Forms

1. Parent:

   

   ALA468766

   ---

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

Calculated Properties

Molecular Weight: 336.39

Molecular Weight (Monoisotopic): 336.1474

AlogP: 2.83

#Rotatable Bonds: ┄

Polar Surface Area: 73.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.32

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 0.09

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: 0.96

References

1. Peterková L, Kmoníčková E, Ruml T, Rimpelová S..  (2020)  Sarco/Endoplasmic Reticulum Calcium ATPase Inhibitors: Beyond Anticancer Perspective.,  63  (5): [PMID:32030976] [10.1021/acs.jmedchem.9b01509]

2. Liu L, Qian X, Yang T, Fang D, Qin Z, Ren B, Li G..  (2022)  Cyclopiazonic Acid and Okaramine Analogues, Including Chlorinated Compounds, from Chrysosporium undulatum YT-1.,  85  (11.0): [PMID:36268672] [10.1021/acs.jnatprod.2c00445]

Source

Source(1):

• Scientific Literature