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Malic acid
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Dicarboxylic Acid
- Subclass: Alpha Hydroxy Acid
| Canonical Smiles | OC(=O)CC(C(=O)O)O |
|---|---|
| InChI | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9) |
| InChIKey | BJEPYKJPYRNKOW-UHFFFAOYSA-N |
| Formula | C4H6O5 |
| HBA | 3 |
| HBD | 3 |
| MW | 134.09 |
| Rotatable Bonds | 3 |
| TPSA | 94.83 |
| LogP | -1.09 |
| Number Rings | 0 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 9 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 134.02 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Euphorbia retusa | Euphorbiaceae | Plantae | 1091645 |
Showing of synonyms
Malic acid
6915-15-7
2-Hydroxybutanedioic acid
617-48-1
2-Hydroxysuccinic acid
Butanedioic acid, hydroxy-
Hydroxysuccinic acid
Kyselina jablecna
Hydroxybutanedioic acid
Pomalus acid
Deoxytetraric acid
Hydroxybutandisaeure
Musashi-no-Ringosan
Caswell No. 537
Monohydroxybernsteinsaeure
R,S(+-)-Malic acid
Malicum acidum
Pomalous acid
FDA 2018
FEMA Number 2655
2-Hydroxyethane-1,2-dicarboxylic acid
Aepfelsaeure
CCRIS 2950
CCRIS 6567
EPA Pesticide Chemical Code 051101
HSDB 1202
Kyselina hydroxybutandiova
AI3-06292
H2mal
EINECS 210-514-9
EINECS 230-022-8
UNII-817L1N4CKP
NSC 25941
NSC-25941
817L1N4CKP
CHEBI:6650
INS NO.296
DTXSID0027640
E296
INS NO. 296
INS-296
DTXCID107640
E-296
EC 210-514-9
EC 230-022-8
MALIC ACID (II)
MALIC ACID [II]
MALIC ACID (USP-RS)
MALIC ACID [USP-RS]
(+-)-Malic acid
MALIC ACID (EP MONOGRAPH)
MALIC ACID (USP IMPURITY)
MALIC ACID [EP MONOGRAPH]
MALIC ACID [USP IMPURITY]
(+-)-Hydroxysuccinic acid
Hydroxybutanedioic acid, (+-)-
Malic Acid1524
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION)
230-022-8
DL-malic acid
Malate
Malic acid, DL-
DL-2-hydroxybutanedioic acid
Dl-Hydroxybutanedioic acid
Alpha-Hydroxysuccinic acid
Succinic acid, hydroxy-
Kyselina jablecna [Czech]
Malic acid [NF]
FEMA No. 2655
Kyselina hydroxybutandiova [Czech]
D,l-malic acid
L-Malic acid-1-13C
Apple acid
(+/-)-Malic acid
MFCD00064212
BUTANEDIOIC ACID, HYDROXY-, (S)-
MLS000084707
(+-)-1-Hydroxy-1,2-ethanedicarboxylic acid
NSC25941
Malic acid (NF)
SMR000019054
DL-Apple Acid
(R)-Hydroxybutanedioic acid
(S)-Hydroxybutanedioic acid
R-Malic acid
.+-.-Malic acid
CAS-6915-15-7
(+/-)-2-Hydroxysuccinic acid
Hydroxybutanedioic acid, (-)-
Racemic malic acid
Malic acid (Standard)
Opera_ID_805
2-hydroxyl-succinic acid
DL-Malic acid, 99%
MALIC ACID [MI]
MALIC ACID,(DL)
2-Hydroxydicarboxylic acid
MALIC ACID [FCC]
SCHEMBL856
2-hydroxy-butanedioic acid
Bmse000046
Bmse000904
MALIC ACID [VANDF]
Malic acid-, (L-form)-
DL-Malic acid, >=99%
Oprea1_130558
Oprea1_624131
MALIC ACID [WHO-DD]
Butanedioic acid, 2-hydroxy-
Butanedioic acid, (.+-.)-
GTPL2480
CHEMBL1455497
BDBM92495
HY-Y1311R
DL-Malic acid, FCC, >=99%
HMS2358H06
HMS3371C13
DL-Malic acid, analytical standard
HY-Y1311
STR03457
(+/-)-HYDROXYSUCCINIC ACID
Tox21_201536
Tox21_300372
S9001
STL283959
HYDROXYBUTANEDIOIC ACID [HSDB]
AKOS000120085
AKOS017278471
CCG-266122
DB12751
FM25003
DL-Malic acid, ReagentPlus(R), 99%
NCGC00043225-02
NCGC00043225-03
NCGC00254259-01
NCGC00259086-01
DL-Malic acid, >=98% (capillary GC)
HYDROXYBUTANEDIOIC ACID, (+/-)-
SY003313
SY009804
DL-Malic acid, ReagentPlus(R), >=99%
DB-016133
DL-Malic acid 1000 microg/mL in Methanol
DL-Malic acid, USP, 99.0-100.5%
CS-0017784
EU-0067046
M0020
NS00008011
DL-Malic acid, SAJ first grade, >=99.0%
EN300-19229
C00711
C03668
D04843
DL-Malic acid, Vetec(TM) reagent grade, 98%
AB00443952-12
Malic acid, meets USP/NF testing specifications
L023999
Q190143
D-Hydroxysuccinic acid
BRD-A18396475-001-15-3
0C9A2DC0-FEA2-4864-B98B-0597CDD0AD06
F0918-0088
Z104473230
Malic acid, United States Pharmacopeia (USP) Reference Standard
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Malic acid, Pharmaceutical Secondary Standard
Certified Reference Material
DL-Malic acid, meets analytical specification of FCC, E296, 99-100.5% (alkalimetric)
- Elgamal A, El Raey M, et al. (2021). Phytochemical profiling and anti-aging activities of Euphorbia retusa extract: In silico and in vitro studies. Arabian Journal of Chemistry, 2021, 14(6), 103159. [View]
Pubchem:
525
Cas:
6915-15-7
Gnps:
CCMSLIB00006677072
Kegg Ligand:
C00711
Chebi:
6650
Nmrshiftdb2:
10016805
Metabolights:
MTBLC6650
Chembl:
CHEMBL1455497
Comptox:
DTXSID0027640
Drugbank:
DB12751
Bindingdb:
92495
CPRiL:
2972
No scaffolds available.
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.88
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -2.27
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.45
- Plasma Protein Binding
- -4.99
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -1.2
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.09
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Toxic
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.61
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.41
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 2.49
- Rat (Acute)
- 1.43
- Rat (Chronic Oral)
- 2.72
- Fathead Minnow
- 3.32
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 279.44
- Hydration Free Energy
- -7.63
- Log(D) at pH=7.4
- -2.92
- Log(P)
- -1.26
- Log S
- -0.32
- Log(Vapor Pressure)
- -6.58
- Melting Point
- 157.98
- pKa Acid
- 2.67
- pKa Basic
- 8.21
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.9105 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.9071 |
| Mexicain | P84346 | MEX1_JACME | Jacaratia mexicana | 3 | 0.9020 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.8998 |
| D-3-phosphoglycerate dehydrogenase | P9WNX3 | SERA_MYCTU | Mycobacterium tuberculosis | 3 | 0.8287 |
| Putative choline kinase | Q5CUP2 | Q5CUP2_CRYPI | Cryptosporidium parvum | 3 | 0.7773 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7689 |
| Geranylgeranyl pyrophosphate synthase BTS1 | Q12051 | GGPPS_YEAST | Saccharomyces cerevisiae | 3 | 0.7613 |
| Ficolin-2 | Q15485 | FCN2_HUMAN | Homo sapiens | 3 | 0.7476 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | O66496 | KDSA_AQUAE | Aquifex aeolicus | 3 | 0.7330 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7061 |