ID: ALA242103

Max Phase: Preclinical

Molecular Formula: C9H11N3O2S

Molecular Weight: 225.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(/C=N/NC(N)=S)cc1O

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

Standard InChI Key:  ARINKVDYBABITQ-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: 9.62

CX Basic pKa: 2.15

CX LogP: 1.20

CX LogD: 1.20

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.40

Np Likeness Score: -1.05

References

1. Du X, Guo C, Hansell E, Doyle PS, Caffrey CR, Holler TP, McKerrow JH, Cohen FE..  (2002)  Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain.,  45  (13): [PMID:12061873] [10.1021/jm010459j]

2. 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]

3. 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]

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

5. 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]

Source

Source(1):

• Scientific Literature