pyruvate

ID: ALA1162144

Chembl Id: CHEMBL1162144

Cas Number: 127-17-3

PubChem CID: 1060

Product Number: P130014

Max Phase: Phase

Molecular Formula: C3H4O3

Molecular Weight: 88.06

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 2-Oxopropanoate | Pyruvate | Pyruvic acid|2-Oxopropanoic acid|127-17-3|acetylformic acid|Pyroracemic acid|2-Oxopropionic acid|alpha-ketopropionic acid|2-Ketopropionic acid|Propanoic acid, 2-oxo-|2-Oxopropansaeure|2-Oxopropanoate|2-Oxopropionsaeure|alpha-Oxopropionsaeure|2-oxo-propionic acid|acide pyruvique|Pyruvic acid (natural)|a-Ketopropionic acid|CH3COCOOH|Brenztraubensaeure|FEMA No. 2970|NSC 179|alpha-keto propionic acid|AI3-11220|.alpha.-Ketopropionic acid|EINECS 204-824-3|UNII-8558G7RUTR|BShow More

Synonyms from Alternative Forms(3): Pyruvate sodium | Sodium 2-Oxo-Propionate | Sodium 2-Oxopropanoate

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

Alternative Forms

  1. Alternative Forms:

    ALA1162144

    Sodium pyruvate
  2. Parent:

    ALA1162144

    PYRUVATE

Associated Targets(Human)

SLC16A7 Tchem Monocarboxylate transporter 2 (11 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC16A3 Tchem Monocarboxylate transporter 4 (196 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC16A10 SLC16A10 protein (28 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO2A1 Tchem Solute carrier organic anion transporter family member 2A1 (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FTO Tchem Alpha-ketoglutarate-dependent dioxygenase FTO (473 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTBP2 Tchem C-terminal-binding protein 2 (36 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Slc22a6 Solute carrier family 22 member 6 (141 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc22a20 Solute carrier family 22 member 20 (86 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc16a1 Monocarboxylate transporter 1 (151 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc16a7 Monocarboxylate transporter 2 (30 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc16a10 Monocarboxylate transporter 10 (73 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ffar3 Free fatty acid receptor 3 (73 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dapA Dihydrodipicolinate synthase (65 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A085R Prolyl 4-hydroxylase (72 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc16a3 Monocarboxylate transporter 4 (4 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
citA Putative citrate synthase 2 (14 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 88.06Molecular Weight (Monoisotopic): 88.0160AlogP: -0.34#Rotatable Bonds: 1
Polar Surface Area: 54.37Molecular Species: ACIDHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 2.93CX Basic pKa: CX LogP: 0.07CX LogD: -3.42
Aromatic Rings: Heavy Atoms: 6QED Weighted: 0.45Np Likeness Score: 0.61

References

1. Mitsakos V, Dobson RC, Pearce FG, Devenish SR, Evans GL, Burgess BR, Perugini MA, Gerrard JA, Hutton CA..  (2008)  Inhibiting dihydrodipicolinate synthase across species: towards specificity for pathogens?,  18  (2): [PMID:18054225] [10.1016/j.bmcl.2007.11.026]
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]