ID: ALA1233654

Max Phase: Preclinical

Molecular Formula: C14H17N3O2S

Molecular Weight: 291.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@H]1CNCCN1S(=O)(=O)c1cccc2cnccc12

Standard InChI:  InChI=1S/C14H17N3O2S/c1-11-9-16-7-8-17(11)20(18,19)14-4-2-3-12-10-15-6-5-13(12)14/h2-6,10-11,16H,7-9H2,1H3/t11-/m0/s1

Standard InChI Key:  BDVFVCGFMNCYPV-NSHDSACASA-N

Molecule Features

Natural Product: Yes

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: 291.38

Molecular Weight (Monoisotopic): 291.1041

AlogP: 1.22

#Rotatable Bonds: 2

Polar Surface Area: 62.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 7.33

CX LogP: 0.68

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.90

Np Likeness Score: -1.17

References

1. He M, Buisine E, Tartar A, Sergheraert C.  (1994)  Design and synthesis of new leads for PKC bisubstrate inhibitors.,  4  (24): [10.1016/S0960-894X(01)80826-X]

2. Woodard CL, Keenan SM, Gerena L, Welsh WJ, Geyer JA, Waters NC..  (2007)  Evaluation of broad spectrum protein kinase inhibitors to probe the architecture of the malarial cyclin dependent protein kinase Pfmrk.,  17  (17): [PMID:17588749] [10.1016/j.bmcl.2007.06.032]

3. Ali HI, Tomita K, Akaho E, Kunishima M, Kawashima Y, Yamagishi T, Ikeya H, Nagamatsu T..  (2008)  Antitumor studies -- part 2: structure-activity relationship study for flavin analogs including investigations on their in vitro antitumor assay and docking simulation into protein tyrosine kinase.,  43  (7): [PMID:18055068] [10.1016/j.ejmech.2007.10.011]

4. Wang H, Yeo SL, Xu J, Xu X, He H, Ronca F, Ting AE, Wang Y, Yu VC, Sim MM..  (2002)  Isolation of streptonigrin and its novel derivative from Micromonospora as inducing agents of p53-dependent cell apoptosis.,  65  (5): [PMID:12027749] [10.1021/np0104572]

5. Herbert JM, Maffrand JP, Taoubi K, Augereau JM, Fouraste I, Gleye J..  (1991)  Verbascoside isolated from Lantana camara, an inhibitor of protein kinase C.,  54  (6): [PMID:1812212] [10.1021/np50078a016]

6. Bain J, Plater L, Elliott M, Shpiro N, Hastie CJ, McLauchlan H, Klevernic I, Arthur JS, Alessi DR, Cohen P..  (2007)  The selectivity of protein kinase inhibitors: a further update.,  408  (3): [PMID:17850214] [10.1042/bj20070797]

7. Engh RA, Girod A, Kinzel V, Huber R, Bossemeyer D..  (1996)  Crystal structures of catalytic subunit of cAMP-dependent protein kinase in complex with isoquinolinesulfonyl protein kinase inhibitors H7, H8, and H89. Structural implications for selectivity.,  271  (42): [PMID:8824261] [10.1074/jbc.271.42.26157]

8. Škedelj V, Tomašić T, Mašič LP, Zega A..  (2011)  ATP-binding site of bacterial enzymes as a target for antibacterial drug design.,  54  (4): [PMID:21235241] [10.1021/jm101121s]

9. Wienen-Schmidt B, Jonker HRA, Wulsdorf T, Gerber HD, Saxena K, Kudlinzki D, Sreeramulu S, Parigi G, Luchinat C, Heine A, Schwalbe H, Klebe G..  (2018)  Paradoxically, Most Flexible Ligand Binds Most Entropy-Favored: Intriguing Impact of Ligand Flexibility and Solvation on Drug-Kinase Binding.,  61  (14): [PMID:29909615] [10.1021/acs.jmedchem.8b00105]

Source

Source(1):

• Scientific Literature