ID: ALA1372

Max Phase: Approved

First Approval: 2008

Molecular Formula: C20H32N6O12S2

Molecular Weight: 612.64

Molecule Type: Small molecule

Representations

Synonyms (1): Oxiglutatione
Synonyms from Alternative Forms(1):

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1

Standard InChI Key:  YPZRWBKMTBYPTK-BJDJZHNGSA-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: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 612.64

Molecular Weight (Monoisotopic): 612.1520

AlogP: -3.88

#Rotatable Bonds: 21

Polar Surface Area: 317.64

Molecular Species: ZWITTERION

HBA: 12

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.44

CX Basic pKa: 9.61

CX LogP: -10.11

CX LogD: -16.60

Aromatic Rings: 0

Heavy Atoms: 40

QED Weighted: 0.04

Np Likeness Score: 0.30

References

1. Biot C, Bauer H, Schirmer RH, Davioud-Charvet E..  (2004)  5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials.,  47  (24): [PMID:15537352] [10.1021/jm0497545]

2. Fernandes J, Gattass CR..  (2009)  Topological polar surface area defines substrate transport by multidrug resistance associated protein 1 (MRP1/ABCC1).,  52  (4): [PMID:19193010] [10.1021/jm801389m]

3. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Kaakoush NO, Asencio C, Mégraud F, Mendz GL..  (2009)  A redox basis for metronidazole resistance in Helicobacter pylori.,  53  (5): [PMID:19223619] [10.1128/aac.01449-08]

7. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

8. Unpublished dataset, 

9. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

10. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

11. PubChem BioAssay data set, 

12. Lenstra DC, Al Temimi AHK, Mecinović J..  (2018)  Inhibition of histone lysine methyltransferases G9a and GLP by ejection of structural Zn(II).,  28  (7): [PMID:29519735] [10.1016/j.bmcl.2018.02.043]

13. Unpublished dataset, 

14. Franck Touret, Magali Gilles, Karine Barral, Antoine Nougairède, Etienne Decroly, Xavier de Lamballerie, Bruno Coutard.  (2020)  In vitro screening of a FDA approved chemical library reveals potential inhibitors of SARS-CoV-2 replication,  [10.1101/2020.04.03.023846]

15. Dubois L, Pietrancosta N, Cabaye A, Fanget I, Debacker C, Gilormini PA, Dansette PM, Dairou J, Biot C, Froissart R, Goupil-Lamy A, Bertrand HO, Acher FC, McCort-Tranchepain I, Gasnier B, Anne C..  (2020)  Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin.,  63  (15): [PMID:32608236] [10.1021/acs.jmedchem.9b02119]

16. Kim HJ, Jung H, Kim S, Seo JK, Kee JM..  (2022)  Identification of a Target Site for Covalent Inhibition of Protein Phosphohistidine Phosphatase 1.,  13  (12.0): [PMID:36518699] [10.1021/acsmedchemlett.2c00450]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• SARS-CoV-2 Screening Data 2020-21