ID: ALA1162144

Max Phase: Phase

Molecular Formula: C3H4O3

Molecular Weight: 88.06

Molecule Type: Small molecule

Representations

Synonyms (2): 2-Oxopropanoate | Pyruvate
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(=O)C(=O)O

Standard InChI:  InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

Standard InChI Key:  LCTONWCANYUPML-UHFFFAOYSA-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: 88.06

Molecular Weight (Monoisotopic): 88.0160

AlogP: -0.34

#Rotatable Bonds: 1

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.93

CX Basic pKa:

CX LogP: 0.07

CX LogD: -3.42

Aromatic Rings: 0

Heavy Atoms: 6

QED Weighted: 0.45

Np Likeness Score: 0.61

References

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2. Kaler G, Truong DM, Khandelwal A, Nagle M, Eraly SA, Swaan PW, Nigam SK..  (2007)  Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.,  282  (33): [PMID:17553798] [10.1074/jbc.m703467200]

3. Chan BS, Endo S, Kanai N, Schuster VL..  (2002)  Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT.,  282  (1): [PMID:11997326] [10.1152/ajprenal.00151.2001]

4. Bröer S, Rahman B, Pellegri G, Pellerin L, Martin JL, Verleysdonk S, Hamprecht B, Magistretti PJ..  (1997)  Comparison of lactate transport in astroglial cells and monocarboxylate transporter 1 (MCT 1) expressing Xenopus laevis oocytes. Expression of two different monocarboxylate transporters in astroglial cells and neurons.,  272  (1): [PMID:9374487] [10.1074/jbc.272.48.30096]

5. Bröer S, Bröer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW..  (1999)  Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes.,  341  (1): [PMID:10417314] [10.1042/0264-6021:3410529]

6. Bröer S, Schneider HP, Bröer A, Rahman B, Hamprecht B, Deitmer JW..  (1998)  Characterization of the monocarboxylate transporter 1 expressed in Xenopus laevis oocytes by changes in cytosolic pH.,  333  (1): [PMID:9639576] [10.1042/bj3330167]

7. Manning Fox JE, Meredith D, Halestrap AP..  (2000)  Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle.,  529  (1): [PMID:11101640] [10.1111/j.1469-7793.2000.00285.x]

8. Lin RY, Vera JC, Chaganti RS, Golde DW..  (1998)  Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter.,  273  (1): [PMID:9786900] [10.1074/jbc.273.44.28959]

9. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H..  (2001)  Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters.,  276  (1): [PMID:11278508] [10.1074/jbc.m009462200]

10. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H..  (2002)  The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location.,  79  (1): [PMID:11827462] [10.1006/geno.2001.6678]

11. Aik W, Demetriades M, Hamdan MK, Bagg EA, Yeoh KK, Lejeune C, Zhang Z, McDonough MA, Schofield CJ..  (2013)  Structural basis for inhibition of the fat mass and obesity associated protein (FTO).,  56  (9): [PMID:23547775] [10.1021/jm400193d]

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. Korwar S, Morris BL, Parikh HI, Coover RA, Doughty TW, Love IM, Hilbert BJ, Royer WE, Kellogg GE, Grossman SR, Ellis KC..  (2016)  Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP).,  24  (12): [PMID:27156192] [10.1016/j.bmc.2016.04.037]

15.  (2001)  Identification of modulators of GPR41 or GPR42 activity, 

16. Unpublished dataset, 

17. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

18.  (2019)  10  (9): [10.1039/C9MD00107G]

19. Langley GW, Abboud MI, Lohans CT, Schofield CJ..  (2019)  Inhibition of a viral prolyl hydroxylase.,  27  (12): [PMID:30737136] [10.1016/j.bmc.2019.01.018]

20. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

21. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

22. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

23. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

24. Puri S, Juvale K..  (2020)  Monocarboxylate transporter 1 and 4 inhibitors as potential therapeutics for treating solid tumours: A review with structure-activity relationship insights.,  199  [PMID:32388280] [10.1016/j.ejmech.2020.112393]

25. Pathirage R, Favrot L, Petit C, Yamsek M, Singh S, Mallareddy JR, Rana S, Natarajan A, Ronning DR..  (2023)  Mycobacterium tuberculosis CitA activity is modulated by cysteine oxidation and pyruvate binding.,  14  (5): [PMID:37252106] [10.1039/d3md00058c]

Source

Source(8):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• TP-search Transporter Database
• Patent Bioactivity Data
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6