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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
Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid.
1985 Jun
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986 Mar
Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients.
1998
Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique.
2001 Jun
Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.
2005 Oct
Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions.
2008 Jul 14
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
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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