ID: ALA242113

Max Phase: Preclinical

Molecular Formula: C8H9N3OS

Molecular Weight: 195.25

Molecule Type: Small molecule

Representations

Synonyms (1): 2-(4-Hydroxybenzylidene)Hydrazinecarbothioamide
Synonyms from Alternative Forms(1):

Canonical SMILES:  NC(=S)N/N=C/c1ccc(O)cc1

Standard InChI:  InChI=1S/C8H9N3OS/c9-8(13)11-10-5-6-1-3-7(12)4-2-6/h1-5,12H,(H3,9,11,13)/b10-5+

Standard InChI Key:  IKDRFCOUGSBGNI-BJMVGYQFSA-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: 195.25

Molecular Weight (Monoisotopic): 195.0466

AlogP: 0.56

#Rotatable Bonds: 2

Polar Surface Area: 70.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.12

CX Basic pKa: 2.48

CX LogP: 1.36

CX LogD: 1.35

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.37

Np Likeness Score: -1.44

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. Lee KC, Thanigaimalai P, Sharma VK, Kim MS, Roh E, Hwang BY, Kim Y, Jung SH..  (2010)  Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis.,  20  (22): [PMID:20863702] [10.1016/j.bmcl.2010.08.114]

3. Aslam MA, Mahmood SU, Shahid M, Saeed A, Iqbal J..  (2011)  Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors.,  46  (11): [PMID:21981981] [10.1016/j.ejmech.2011.09.009]

4. da Silva JB, Navarro DM, da Silva AG, Santos GK, Dutra KA, Moreira DR, Ramos MN, Espíndola JW, de Oliveira AD, Brondani DJ, Leite AC, Hernandes MZ, Pereira VR, da Rocha LF, de Castro MC, de Oliveira BC, Lan Q, Merz KM..  (2015)  Thiosemicarbazones as Aedes aegypti larvicidal.,  100  [PMID:26087027] [10.1016/j.ejmech.2015.04.061]

5. 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]

6. 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]

7. Mathew B, Baek SC, Grace Thomas Parambi D, Pil Lee J, Joy M, Annie Rilda PR, Randev RV, Nithyamol P, Vijayan V, Inasu ST, Mathew GE, Lohidakshan KK, Kumar Krishnan G, Kim H..  (2018)  Selected aryl thiosemicarbazones as a new class of multi-targeted monoamine oxidase inhibitors.,  9  (11): [PMID:30568755] [10.1039/C8MD00399H]

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

Source

Source(1):

• Scientific Literature