ID: ALA398206

Max Phase: Preclinical

Molecular Formula: C9H11N3OS

Molecular Weight: 209.27

Molecule Type: Small molecule

Representations

Synonyms (2): 2-(4-Methoxybenzylidene)Hydrazinecarbothioamide | 4-Methoxybenzaldehyde Thiosemicarbazone
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1ccc(/C=N/NC(N)=S)cc1

Standard InChI:  InChI=1S/C9H11N3OS/c1-13-8-4-2-7(3-5-8)6-11-12-9(10)14/h2-6H,1H3,(H3,10,12,14)/b11-6+

Standard InChI Key:  TUNWURMRBJWUFJ-IZZDOVSWSA-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: 209.27

Molecular Weight (Monoisotopic): 209.0623

AlogP: 0.86

#Rotatable Bonds: 3

Polar Surface Area: 59.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.71

CX Basic pKa: 2.55

CX LogP: 1.51

CX LogD: 1.51

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.44

Np Likeness Score: -1.81

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. Karki SS, Thota S, Darj SY, Balzarini J, De Clercq E..  (2007)  Synthesis, anticancer, and cytotoxic activities of some mononuclear Ru(II) compounds.,  15  (21): [PMID:17765549] [10.1016/j.bmc.2007.08.014]

3. 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]

4. 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]

5. PubChem BioAssay data set, 

6. 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]

7. 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]

8. Ferreira FB, Pereira TM, Souza DLN, Lopes DS, Freitas V, Ávila VMR, Kümmerle AE, Sant'Anna CMR..  (2017)  Structure-Based Discovery of Thiosemicarbazone Metalloproteinase Inhibitors for Hemorrhage Treatment in Snakebites.,  8  (11): [PMID:29152044] [10.1021/acsmedchemlett.7b00186]

9. 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]

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

Source

Source(2):

• Scientific Literature
• PubChem BioAssays