fumarate

ID: ALA503160

Chembl Id: CHEMBL503160

Cas Number: 110-17-8

PubChem CID: 444972

Product Number: F110741B

Max Phase: Approved

Molecular Formula: C4H4O4

Molecular Weight: 116.07

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-butenedioic acid, (e)- | Allomaleic-acid | Boletic-acid | Fumarate | Fumaric acid | Fumaricum acidum | E-297 | FEMA NO. 2488 | INS NO.297 | INS-297 | NSC-2752 | fumaric acid|110-17-8|trans-Butenedioic acid|Allomaleic acid|fumarate|Lichenic acid|Boletic acid|2-Butenedioic acid|(2E)-but-2-enedioic acid|Tumaric acid|trans-1,2-Ethylenedicarboxylic acid|Allomalenic acid|But-2-enedioic acid|trans-2-Butenedioic acid|Butenedioic acid|(E)-2-Butenedioic acid|Fumaricum acidum|2-Butenedioic acid, (E)-|KysShow More⌵

Canonical SMILES:  O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

Standard InChI Key:  VZCYOOQTPOCHFL-OWOJBTEDSA-N

Alternative Forms

1. Parent:

   

   ALA503160

   FUMARIC ACID

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: 116.07

Molecular Weight (Monoisotopic): 116.0110

AlogP: -0.29

#Rotatable Bonds: 2

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: ┄

CX LogP: -0.04

CX LogD: -6.51

Aromatic Rings: ┄

Heavy Atoms: 8

QED Weighted: 0.49

Np Likeness Score: 0.54

References

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2. Rose NR, Ng SS, Mecinović J, Liénard BM, Bello SH, Sun Z, McDonough MA, Oppermann U, Schofield CJ..  (2008)  Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases.,  51  (22): [PMID:18942826] [10.1021/jm800936s]

3. Stubbs CJ, Loenarz C, Mecinović J, Yeoh KK, Hindley N, Liénard BM, Sobott F, Schofield CJ, Flashman E..  (2009)  Application of a proteolysis/mass spectrometry method for investigating the effects of inhibitors on hydroxylase structure.,  52  (9): [PMID:19364117] [10.1021/jm900285r]

4. Su KL, Chang KY, Hung HC..  (2009)  Effects of structural analogues of the substrate and allosteric regulator of the human mitochondrial NAD(P)+-dependent malic enzyme.,  17  (15): [PMID:19595601] [10.1016/j.bmc.2009.06.052]

5. Davis RA, Innocenti A, Poulsen SA, Supuran CT..  (2010)  Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.,  18  (1): [PMID:19962903] [10.1016/j.bmc.2009.11.021]

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. van Veldhoven JP, Blad CC, Artsen CM, Klopman C, Wolfram DR, Abdelkadir MJ, Lane JR, Brussee J, Ijzerman AP..  (2011)  Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).,  21  (9): [PMID:21167710] [10.1016/j.bmcl.2010.11.091]

9. PubChem BioAssay data set, 

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

11. Leung IK, Demetriades M, Hardy AP, Lejeune C, Smart TJ, Szöllössi A, Kawamura A, Schofield CJ, Claridge TD..  (2013)  Reporter ligand NMR screening method for 2-oxoglutarate oxygenase inhibitors.,  56  (2): [PMID:23234607] [10.1021/jm301583m]

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17. British National Formulary (72nd edition), 

18.  (2001)  Identification of modulators of GPR41 or GPR42 activity, 

19. Macegoniuk K, Kowalczyk R, Rudzińska A, Psurski M, Wietrzyk J, Berlicki Ł..  (2017)  Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.,  27  (6): [PMID:28236590] [10.1016/j.bmcl.2017.02.022]

20. Unpublished dataset, 

21. Huang Y, Wei L, Han X, Chen H, Ren Y, Xu Y, Song R, Rao L, Su C, Peng C, Feng L, Wan J..  (2019)  Discovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects.,  184  [PMID:31589992] [10.1016/j.ejmech.2019.111749]

22. 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]

23. Shen CC, Wei WC, Lin LC..  (2019)  Diterpenoids and Bisnorditerpenoids from Blumea aromatica.,  82  (11): [PMID:31646857] [10.1021/acs.jnatprod.9b00674]

24. Tiwari AD, Guan Y, Grabowski DR, Maciejewski JP, Jha BK, Phillips JG..  (2021)  SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.,  39  [PMID:33894507] [10.1016/j.bmc.2021.116141]

25. Perry GS, Das M, Woon ECY..  (2021)  Inhibition of AlkB Nucleic Acid Demethylases: Promising New Epigenetic Targets.,  64  (23.0): [PMID:34792334] [10.1021/acs.jmedchem.1c01694]

26. Galbiati A, Zana A, Conti P..  (2020)  Covalent inhibitors of GAPDH: From unspecific warheads to selective compounds.,  207  [PMID:32898762] [10.1016/j.ejmech.2020.112740]

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Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary