(2S)-2-ammonio-4-(S-butylsulfonimidoyl)butanoate

ID: ALA1609891

Chembl Id: CHEMBL1609891

Max Phase: Phase

Molecular Formula: C8H18N2O3S

Molecular Weight: 222.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Buthionine sulfoxamine | Buthionine sulfoximine | Butionine sulfoximine | Dl-buthionine (s,r)-sulfoximine | L-Buthionine(S,R)-Sulfoximine | L-Buthionine-Sulfoximine | NSC-381100

Canonical SMILES:  CCCC[S+](=N)([O-])CC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7H,2-6,9H2,1H3,(H2-,10,11,12,13)/t7-,14?/m0/s1

Standard InChI Key:  WDFRNLYXRQXXFS-CVSPRKDYSA-N

Alternative Forms

1. Parent:

   

   ALA1609891

   BUTHIONINE SULFOXIMINE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 222.31

Molecular Weight (Monoisotopic): 222.1038

AlogP: 0.64

#Rotatable Bonds: 7

Polar Surface Area: 110.23

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.18

CX Basic pKa: 9.09

CX LogP: -2.97

CX LogD: -2.98

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.55

Np Likeness Score: 0.60

References

1. Katoh M, Hiratake J, Kato H, Oda J.  (1996)  Mechanism-based inactivation of E. coli -glutamylcysteine synthetase by phosphinic acid- and sulfoximine-based transition-state analogues,  6  (13): [10.1016/S0960-894X(96)00247-8]

2. Lu J, Chew EH, Holmgren A..  (2007)  Targeting thioredoxin reductase is a basis for cancer therapy by arsenic trioxide.,  104  (30): [PMID:17640917] [10.1073/pnas.0701549104]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. Faúndez M, López-Muñoz R, Torres G, Morello A, Ferreira J, Kemmerling U, Orellana M, Maya JD..  (2008)  Buthionine sulfoximine has anti-Trypanosoma cruzi activity in a murine model of acute Chagas' disease and enhances the efficacy of nifurtimox.,  52  (5): [PMID:18332173] [10.1128/aac.01454-07]

5. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

6. PubChem BioAssay data set, 

7. Goldsborough AS, Handley MD, Dulcey AE, Pluchino KM, Kannan P, Brimacombe KR, Hall MD, Griffiths G, Gottesman MM..  (2011)  Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin.,  54  (14): [PMID:21657271] [10.1021/jm2001663]

8. Ahmad R, Mishra R, Tewari N, Tripathi R, Srivastava AK, Walter RD.  (2004)  MODULATION OF FILARIAL GLUTATHIONE-S-TRANSFERASE(S) ACTIVITY: A POSSIBILITY TOWARDS THE SYNTHESIS OF NEW CLASSES OF ANTIFILARIAL AGENTS,  13  (8): [10.1007/s00044-004-0113-8]

9. Open TG-GATES,  [10.6019/CHEMBL3885861]

10. Unpublished dataset, 

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Open TG-GATEs