5,12-dihydroxy-8,9-bis((S)-2-hydroxypropyl)-7,10-dimethoxyperyleno[1,12-def][1,3]dioxepine-6,11-dione

ID: ALA2323033

Chembl Id: CHEMBL2323033

Cas Number: 35082-49-6

PubChem CID: 360901

Max Phase: Preclinical

Molecular Formula: C29H26O10

Molecular Weight: 534.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C[C@H](C)O)c2c3c(C[C@H](C)O)c(OC)c(=O)c4c(O)cc5c(c6c(cc(O)c(c1=O)c62)OCO5)c43

Standard InChI:  InChI=1S/C29H26O10/c1-10(30)5-12-18-19-13(6-11(2)31)29(37-4)27(35)21-15(33)8-17-23(25(19)21)22-16(38-9-39-17)7-14(32)20(24(18)22)26(34)28(12)36-3/h7-8,10-11,30-33H,5-6,9H2,1-4H3/t10-,11-/m0/s1

Standard InChI Key:  DGAZLNHJYDOWLG-QWRGUYRKSA-N

Alternative Forms

1. Parent:

   

   ALA2323033

   Cercosporin, pure

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: 534.52

Molecular Weight (Monoisotopic): 534.1526

AlogP: 2.90

#Rotatable Bonds: 6

Polar Surface Area: 151.98

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.42

CX Basic pKa: 3.19

CX LogP: 3.34

CX LogD: 1.85

Aromatic Rings: 5

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 1.04

References

1. Zhang M, Catrow JL, Ji H..  (2013)  High-Throughput Selectivity Assays for Small-Molecule Inhibitors of β-Catenin/T-Cell Factor Protein-Protein Interactions.,  4  (2): [PMID:24900664] [10.1021/ml300367f]

2. Hahne G, Grossmann TN..  (2013)  Direct targeting of β-catenin: Inhibition of protein-protein interactions for the inactivation of Wnt signaling.,  21  (14): [PMID:23566764] [10.1016/j.bmc.2013.02.050]

3. Catrow JL, Zhang Y, Zhang M, Ji H..  (2015)  Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein-Protein Interaction through the Optimization of the Acyl Hydrazone Moiety.,  58  (11): [PMID:25985283] [10.1021/acs.jmedchem.5b00223]

4.  (2016)  Substituted 1H-indazol-1-ol analogs as inhibitors of beta catenin/Tcf protein-protein interactions, 

5. McCoy MA, Spicer D, Wells N, Hoogewijs K, Fiedler M, Baud MGJ..  (2022)  Biophysical Survey of Small-Molecule β-Catenin Inhibitors: A Cautionary Tale.,  65  (10.0): [PMID:35581674] [10.1021/acs.jmedchem.2c00228]

Source

Source(2):

• Scientific Literature
• BindingDB Database