ID: ALA242104

Max Phase: Preclinical

Molecular Formula: C9H11N3O2S

Molecular Weight: 225.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(/C=N/NC(N)=S)ccc1O

Standard InChI:  InChI=1S/C9H11N3O2S/c1-14-8-4-6(2-3-7(8)13)5-11-12-9(10)15/h2-5,13H,1H3,(H3,10,12,15)/b11-5+

Standard InChI Key:  FJQYXPHDGKUTQE-VZUCSPMQSA-N

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

Properties

Molecular Weight: 225.27

Molecular Weight (Monoisotopic): 225.0572

AlogP: 0.57

#Rotatable Bonds: 3

Polar Surface Area: 79.87

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.59

CX Basic pKa: 2.16

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.40

Np Likeness Score: -1.04

References

1. Xue CB, Zhang L, Luo WC, Xie XY, Jiang L, Xiao T..  (2007)  3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.,  15  (5): [PMID:17258462] [10.1016/j.bmc.2006.12.038]

2. de Oliveira RB, de Souza-Fagundes EM, Soares RP, Andrade AA, Krettli AU, Zani CL..  (2008)  Synthesis and antimalarial activity of semicarbazone and thiosemicarbazone derivatives.,  43  (9): [PMID:18222568] [10.1016/j.ejmech.2007.11.012]

3. Soares MA, Almeida MA, Marins-Goulart C, Chaves OA, Echevarria A, de Oliveira MCC..  (2017)  Thiosemicarbazones as inhibitors of tyrosinase enzyme.,  27  (15): [PMID:28583798] [10.1016/j.bmcl.2017.05.057]

4. Linciano P, Moraes CB, Alcantara LM, Franco CH, Pascoalino B, Freitas-Junior LH, Macedo S, Santarem N, Cordeiro-da-Silva A, Gul S, Witt G, Kuzikov M, Ellinger B, Ferrari S, Luciani R, Quotadamo A, Costantino L, Costi MP..  (2018)  Aryl thiosemicarbazones for the treatment of trypanosomatidic infections.,  146  [PMID:29407968] [10.1016/j.ejmech.2018.01.043]

5. Hałdys K, Latajka R..  (2019)  Thiosemicarbazones with tyrosinase inhibitory activity.,  10  (3): [PMID:31015905] [10.1039/C9MD00005D]

6. Guo C,Wang L,Li X,Wang S,Yu X,Xu K,Zhao Y,Luo J,Li X,Jiang B,Shi D.  (2019)  Discovery of Novel Bromophenol-Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer.,  62  (6.0): [PMID:30844273] [10.1021/acs.jmedchem.8b01946]

7. Ayoup MS, Abu-Serie MM, Awad LF, Teleb M, Ragab HM, Amer A..  (2021)  Halting colorectal cancer metastasis via novel dual nanomolar MMP-9/MAO-A quinoxaline-based inhibitors; design, synthesis, and evaluation.,  222  [PMID:34116327] [10.1016/j.ejmech.2021.113558]

Source

Source(1):

• Scientific Literature