2,3,4,5-tetrachloro-6-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

ID: ALA1205178

Chembl Id: CHEMBL1205178

Cas Number: 2134-15-8

PubChem CID: 407912

Max Phase: Preclinical

Molecular Formula: C20H4Br4Cl4O5

Molecular Weight: 785.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1c(Cl)c(Cl)c(Cl)c(Cl)c1-c1c2cc(Br)c(=O)c(Br)c-2oc2c(Br)c(O)c(Br)cc12

Standard InChI:  InChI=1S/C20H4Br4Cl4O5/c21-5-1-3-7(8-9(20(31)32)13(26)15(28)14(27)12(8)25)4-2-6(22)17(30)11(24)19(4)33-18(3)10(23)16(5)29/h1-2,29H,(H,31,32)

Standard InChI Key:  RIVZUHBWXRGVOG-UHFFFAOYSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1205178

   D&C Red No. 28

2. Parent:

   

   ALA1205178

   2,3,4,5-tetrachloro-6-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

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: 785.67

Molecular Weight (Monoisotopic): 779.5546

AlogP: 9.63

#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: 2.52

CX Basic pKa: 1.84

CX LogP: 8.16

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.12

Np Likeness Score: 0.46

References

1. 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]

2. Mihalyi A, Jamshidi S, Slikas J, Bugg TD..  (2014)  Identification of novel inhibitors of phospho-MurNAc-pentapeptide translocase MraY from library screening: Isoquinoline alkaloid michellamine B and xanthene dye phloxine B.,  22  (17): [PMID:25127465] [10.1016/j.bmc.2014.07.035]

3. 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]

4. Kim M, Ha JH, Choi J, Kim BR, Gapsys V, Lee KO, Jee JG, Chakrabarti KS, de Groot BL, Griesinger C, Ryu KS, Lee D..  (2022)  Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.,  65  (3.0): [PMID:34957824] [10.1021/acs.jmedchem.1c01664]

5. Bugg TD, Rodolis MT, Mihalyi A, Jamshidi S..  (2016)  Inhibition of phospho-MurNAc-pentapeptide translocase (MraY) by nucleoside natural product antibiotics, bacteriophage ϕX174 lysis protein E, and cationic antibacterial peptides.,  24  (24): [PMID:27021004] [10.1016/j.bmc.2016.03.018]

Source

Source(1):

• Scientific Literature