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Malic acid

Athanor · official

C4H6O5 · 134.09 g/mol

IUPAC name: (2S)-2-hydroxybutanedioic acid

Also called malate, apple acid, hydroxybutanedioic acid, E296

Metabolites
Open in Athanor
The structure of Malic acid
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses skin irritation · Causes serious eye irritation

Names and identifiers

IUPAC name
(2S)-2-hydroxybutanedioic acid
Synonyms
malate, apple acid, hydroxybutanedioic acid
+ 40 more

E296, L-Malic acid, (2S)-2-Hydroxybutanedioic acid, (-)-Malic acid, (-)-Hydroxysuccinic acid, S-(-)-Malic acid, Malic acid, L-, Malic acid L-(-)-form, Hydroxysuccinnic acid (-), Butanedioic acid, 2-hydroxy-, (2S)-, Hydroxybutanedioic acid, (S)-, J3TZF807X5, NSC9232, 2-Hydroxybutanedioic acid, (S)-, NSC 9232, EINECS 202-601-5, L-MALIC ACID [FHFI], L-MALIC ACID [WHO-DD], DTXSID30273987, MALIC ACID L-(-)-FORM [MI], MALIC ACID, L-(II), MALIC ACID, L-[II], RefChem:796817, (-)-Hydroxybutanedioic Acid, DTXCID10819943, hydron;(2S)-2-hydroxybutanedioate, 202-601-5, L-(-)-Malic acid, (S)-2-hydroxysuccinic acid, (S)-Malic acid, L(-)-Malic acid, L-Apple acid, L-Hydroxybutanedioic acid, Apple acid, S-2-Hydroxybutanedioic acid, (-)-L-Malic acid, Butanedioic acid, hydroxy-, (2S)-, MFCD00064213, L-2-Hydroxybutanedioic acid, (S)-malate

Molecular formula
C4H6O5
Empirical formula
C4H6O5
Molecular weight
134.09 g/mol
Exact mass
134.02152
CAS number
97-67-6
PubChem CID
222656
Canonical SMILES
C(C(C(=O)O)O)C(=O)O
Isomeric SMILES
C([C@@H](C(=O)O)O)C(=O)O
InChI
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChIKey
BJEPYKJPYRNKOW-REOHCLBHSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
9
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.5
H-bond donors
3
H-bond acceptors
3 computed here · PubChem 5
Rotatable bonds
3
TPSA (Ų)
94.8
Formal charge
0
XLogP3
-1.3 PubChem
Complexity
129 PubChem
Stereocenters
1 definedCIP: C5: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C35.83%
  • H4.51%
  • O59.66%

Isotope pattern

100%134.0224.6%135.0251.1%136.026

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
-1.09 Crippen (Wildman and Crippen 1999)
log S (water solubility)
0.22 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.6 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 134.09
  • log P ≤ 5 (Crippen): -1.09
  • H-bond donors ≤ 5: 3
  • H-bond acceptors ≤ 10: 3

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 1,589 company reports to ECHA. Source [1].

  • Harmful or irritant
  • H315Causes skin irritation (18% of reports)
  • H319Causes serious eye irritation (97.7% of reports)

Precautionary statements: P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364

View all classifications (2)
  • [1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 0.4% (7 of 1589) of reports.
  • [1] European Chemicals Agency (ECHA) · 1,589 reports · WarningH315, H319

Safety data sheets on the supplier’s page: TargetMol, Protheragen, Achemtek.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  7. ·Literature on PubChem

Data last updated 2026-10-14.