ID: ALA1160028

Max Phase: Preclinical

Molecular Formula: C20H8I4O5

Molecular Weight: 835.89

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)c1ccccc1-c1c2cc(I)c(=O)c(I)c-2oc2c(I)c(O)c(I)cc12

Standard InChI:  InChI=1S/C20H8I4O5/c21-11-5-9-13(7-3-1-2-4-8(7)20(27)28)10-6-12(22)17(26)15(24)19(10)29-18(9)14(23)16(11)25/h1-6,25H,(H,27,28)

Standard InChI Key:  LAINPTZBIXYTIZ-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: 835.89

Molecular Weight (Monoisotopic): 835.6551

AlogP: 6.39

#Rotatable Bonds: 2

Polar Surface Area: 87.74

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.53

CX Basic pKa: 2.04

CX LogP: 6.68

CX LogD: 1.46

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.18

Np Likeness Score: 0.30

References

1. Mautner HG, Merrill RE, Currier SF, Harvey G..  (1981)  Interaction of aromatic dyes with the coenzyme A binding site of choline acetyltransferase.,  24  (12): [PMID:7310833] [10.1021/jm00144a035]

2. Pietrancosta N, Kessler A, Favre-Besse FC, Triballeau N, Quentin T, Giros B, El Mestikawy S, Acher FC..  (2010)  Rose Bengal analogs and vesicular glutamate transporters (VGLUTs).,  18  (18): [PMID:20708942] [10.1016/j.bmc.2010.06.069]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Shibui Y, Oyama T, Okazawa M, Yoshimori A, Abe H, Uchiumi F, Tanuma SI..  (2020)  Structural insights into the active site of poly(ADP-ribose) glycohydrolase using docking modes of 6-hydroxy-3H-xanthen-3-one derivative inhibitors.,  28  (3): [PMID:31879180] [10.1016/j.bmc.2019.115249]

6. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6