ID: ALA243185

Max Phase: Preclinical

Molecular Formula: C8H9N3S

Molecular Weight: 179.25

Molecule Type: Small molecule

Representations

Synonyms (5): (E)-1-Benzylidenethiosemicarbazide | 2-Benzylidenehydrazinecarbothioamide | Benzaldehyde N-Allylthiosemicarbazone | Benzaldehyde Thiosemicarbazone | Phenylthiosemicarbazone
Synonyms from Alternative Forms(5):

Canonical SMILES:  NC(=S)N/N=C/c1ccccc1

Standard InChI:  InChI=1S/C8H9N3S/c9-8(12)11-10-6-7-4-2-1-3-5-7/h1-6H,(H3,9,11,12)/b10-6+

Standard InChI Key:  UYHCMAZIKNVDSX-UXBLZVDNSA-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: 179.25

Molecular Weight (Monoisotopic): 179.0517

AlogP: 0.85

#Rotatable Bonds: 2

Polar Surface Area: 50.41

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.71

CX Basic pKa: 2.85

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.40

Np Likeness Score: -2.11

References

1. Dimmock JR, Sidhu KK, Thayer RS, Mack P, Duffy MJ, Reid RS, Quail JW, Pugazhenthi U, Ong A, Bikker JA..  (1993)  Anticonvulsant activities of some arylsemicarbazones displaying potent oral activity in the maximal electroshock screen in rats accompanied by high protection indices.,  36  (16): [PMID:8360870] [10.1021/jm00068a001]

2. Rastelli G, Pacchioni S, Sirawaraporn W, Sirawaraporn R, Parenti MD, Ferrari AM..  (2003)  Docking and database screening reveal new classes of Plasmodium falciparum dihydrofolate reductase inhibitors.,  46  (14): [PMID:12825927] [10.1021/jm030781p]

3. Parenti MD, Pacchioni S, Ferrari AM, Rastelli G..  (2004)  Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach.,  47  (17): [PMID:15293997] [10.1021/jm040769c]

4. 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]

5. Thanigaimalai P, Hoang TA, Lee KC, Bang SC, Sharma VK, Yun CY, Roh E, Hwang BY, Kim Y, Jung SH..  (2010)  Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells.,  20  (9): [PMID:20359890] [10.1016/j.bmcl.2010.02.067]

6. 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]

7. PubChem BioAssay data set, 

8. 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]

9. 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]

10. 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]

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

Source

Source(2):

• Scientific Literature
• PubChem BioAssays