ID: ALA397565

Max Phase: Preclinical

Molecular Formula: C5H12N2O2S

Molecular Weight: 164.23

Molecule Type: Small molecule

Representations

Canonical SMILES:  NCCSC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C5H12N2O2S/c6-1-2-10-3-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1

Standard InChI Key:  GHSJKUNUIHUPDF-BYPYZUCNSA-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: 164.23

Molecular Weight (Monoisotopic): 164.0619

AlogP: -0.91

#Rotatable Bonds: 5

Polar Surface Area: 89.34

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.52

CX Basic pKa: 9.82

CX LogP: -3.81

CX LogD: -5.09

Aromatic Rings: 0

Heavy Atoms: 10

QED Weighted: 0.46

Np Likeness Score: 0.53

References

1. Ogo N, Oishi S, Matsuno K, Sawada J, Fujii N, Asai A..  (2007)  Synthesis and biological evaluation of L-cysteine derivatives as mitotic kinesin Eg5 inhibitors.,  17  (14): [PMID:17524640] [10.1016/j.bmcl.2007.04.101]

2. Blount KF, Wang JX, Lim J, Sudarsan N, Breaker RR..  (2007)  Antibacterial lysine analogs that target lysine riboswitches.,  3  (1): [PMID:17143270] [10.1038/nchembio842]

3. PubChem BioAssay data set, 

4. Shirota FN, Nagasawa HT, Elberling JA..  (1977)  Potential inhibitors of collagen biosynthesis. 5,5-Difluoro-DL-lysine and 5,5-dimethyl-DL-lysine and their activation by lysyl-tRNA ligase.,  20  (12): [PMID:412965] [10.1021/jm00222a017]

5. Matzner D, Mayer G..  (2015)  (Dis)similar Analogues of Riboswitch Metabolites as Antibacterial Lead Compounds.,  58  (8): [PMID:25603286] [10.1021/jm500868e]

6.  (2019)  10  (9): [10.1039/C9MD00107G]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays