U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4
Molecular Weight 116.0722
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Maleic Acid

SMILES

OC(=O)\C=C/C(O)=O

InChI

InChIKey=VZCYOOQTPOCHFL-UPHRSURJSA-N
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20647102 | https://www.ncbi.nlm.nih.gov/pubmed/19595601

Maleic acid monosodium salt. Used in water soluble polymers preparation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96KS0
Gene ID: 112398.0
Gene Symbol: EGLN2
Target Organism: Homo sapiens (Human)
120.0 µM [IC50]
Target ID: Q9H6Z9
Gene ID: 112399.0
Gene Symbol: EGLN3
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9GZT9
Gene ID: 54583.0
Gene Symbol: EGLN1
Target Organism: Homo sapiens (Human)
80.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Curcumin prevents maleate-induced nephrotoxicity: relation to hemodynamic alterations, oxidative stress, mitochondrial oxygen consumption and activity of respiratory complex I.
2014-11
Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling.
2013-08
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013-06
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010-05
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
2010-03
Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions.
2008-07-14
Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles.
2006-08-01
Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts.
2006-06
Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.
2005-10
Determination of ergometrine maleate by fluorescence detection.
2005-06-01
Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics.
2004-03-30
Molecular machinery for non-vesicular trafficking of ceramide.
2003-12-18
Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers.
2003-08
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition.
2002-11-27
Molecular mechanism for the regulation of human mitochondrial NAD(P)+-dependent malic enzyme by ATP and fumarate.
2002-07
The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy.
2002-05-15
Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique.
2001-06
Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC.
2000-07
Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer.
1999-10-16
In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions.
1999-08
Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma.
1998-11
Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces.
1998
A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids.
1998
Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients.
1998
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996-12
Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats.
1996-03
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995-12
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.
1994-06
Disposition of [14C]velnacrine maleate in rats, dogs, and humans.
1993-11-01
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Ocular surface alteration after long-term treatment with an antiglaucomatous drug.
1992-07
Antifungal activity of fumaric acid in mice infected with Candida albicans.
1991-11
Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.
1991-01-02
Menstrual migraine and intermittent ergonovine therapy.
1989-06
Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan.
1988-09
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986-03
Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid.
1985-06
The influence of long-term treatment with timolol on human tear lysozyme albumin content.
1982
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In group of dogs experimental Fanconi syndrome (generalized proximal tubular dysfunction) was induced with maleic acid (25 mg/kg iv, pH 7.3). https://www.ncbi.nlm.nih.gov/pubmed/1858895
Single dose of 0 mg/kg (control group), 6 mg/kg (low-dose group), and 60 mg/kg (high-dose group) of MA (Maleic acid) with DDW (double deionized water) as the vehicle were administered to SD rats via oral gavage.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Maleic acid-induced inhibition of sugar and amino acid transport in the rat renal tubule was studied.
Forty-five extracted human maxillary central incisors were sectioned longitudinally into a total of 90 segments, were embedded in auto polymerizing acrylic resin, and were grounded flat with silicon carbide abrasive papers. Based on the test solutions used, samples were divided randomly into three groups: (1) the EDTA group, 1 mL of 17% EDTA for 1 minute (n = 30), (2) the maleic acid group, 1 mL of 7% maleic acid for 1 minute (n = 30), and (3) the control group, 1 mL of 0.9% saline for 1 minute (n = 30). Every group was then divided into two subgroups of 15 specimens each. In group 1a, 2a, and 3a, specimens were used to determine the microhardness of the root canal dentine in the coronal, middle, and apical third using Vicker's hardness tester. In groups 1b, 2b, and 3b, specimens were used for the determination of surface roughness of the root canal dentine using a roughness tester (Surtronic, Leicester, England). Maleic acid reduced the microhardness of root dentin similar to EDTA but increased the surface roughness significantly more than EDTA.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:26 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:26 GMT 2025
Record UNII
91XW058U2C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-25940
Preferred Name English
Maleic Acid
EP   HSDB   II   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
MALEIC ACID [MART.]
Common Name English
Maleic acid [WHO-DD]
Common Name English
MALEIC ACID [MI]
Common Name English
SODIUM AUROTHIOMALATE IMPURITY A [EP IMPURITY]
Common Name English
MALEIC ACID [HSDB]
Common Name English
MALEIC ACID [USP IMPURITY]
Common Name English
MALEIC ACID [EP MONOGRAPH]
Common Name English
(Z)-BUTENEDIOIC ACID
Systematic Name English
MALEIC ACID [II]
Common Name English
MALEIC ACID [USP-RS]
Common Name English
MALIC ACID IMPURITY B [EP IMPURITY]
Common Name English
cis-Butenedioic acid
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C718
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1374500
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PRIMARY
ECHA (EC/EINECS)
203-742-5
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PRIMARY
RXCUI
1426330
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PRIMARY RxNorm
EVMPD
SUB12134MIG
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PRIMARY
CHEBI
30780
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
NSC
25940
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
PUBCHEM
444266
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
MERCK INDEX
m7037
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY Merck Index
RXCUI
1426331
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
DRUG BANK
DB04299
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
FDA UNII
91XW058U2C
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
SMS_ID
100000080141
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
CHEBI
18300
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
NCI_THESAURUS
C25951
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
CAS
110-16-7
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
HSDB
666
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
MESH
C030272
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID8021517
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
DAILYMED
91XW058U2C
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
WIKIPEDIA
MALEIC ACID
Created by admin on Mon Mar 31 17:47:26 GMT 2025 , Edited by admin on Mon Mar 31 17:47:26 GMT 2025
PRIMARY
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