Oxaloacetic acid
Athanor · official
C4H4O5 · 132.07 g/mol
IUPAC name: 2-oxobutanedioic acid
Also called oxaloacetate, OAA, oxalacetic acid
DangerCauses severe skin burns and eye damage · Causes serious eye irritationNames and identifiers
- IUPAC name
- 2-oxobutanedioic acid
- Synonyms
- oxaloacetate, OAA, oxalacetic acid
+ 35 more
2-Oxobutanedioic acid, Ketosuccinic acid, Oxosuccinic acid, 2-Ketosuccinic acid, Butanedioic acid, oxo-, Bioepg, 2-oxo-butanedioic acid, keto-oxaloacetate, DTXSID8021646, NSC-77688, 2F399MM81J, DTXCID901646, CHEBI:30744, Acid, Oxalacetic, Acid, Oxaloacetic, 2 Ketosuccinic Acid, 2 oxo Butanedioic Acid, RefChem:857040, Oxalacetic acid trans-(z)-enol, 206-329-8, 2-Oxosuccinic acid, Oxobutanedioic acid, Oxalacetic acetic, MFCD00002592, alpha-Ketosuccinic acid, Butanedioic acid, 2-oxo-, Oxaloethanoic acid, NSC 77688, Anhydrous enol-oxaloacetate, 2-oxobutanedioate, Oxalacetic acid hybri-maxtm, OxalaceticAcid, FO12113, EINECS 206-329-8, Ketosuccinate
- Molecular formula
- C4H4O5
- Empirical formula
- C4H4O5
- Molecular weight
- 132.07 g/mol
- Exact mass
- 132.00587
- CAS number
- 328-42-7
- PubChem CID
- 970
- Canonical SMILES
- C(C(=O)C(=O)O)C(=O)O
- Isomeric SMILES
- C(C(=O)C(=O)O)C(=O)O
- InChI
- InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
- InChIKey
- KHPXUQMNIQBQEV-UHFFFAOYSA-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)
- 0.25
- H-bond donors
- 2
- H-bond acceptors
- 3 computed here · PubChem 5
- Rotatable bonds
- 3
- TPSA (Ų)
- 91.7
- Formal charge
- 0
- XLogP3
- -0.6 PubChem
- Complexity
- 158 PubChem
- Stereocenters
- None
- 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
- C36.38%
- H3.05%
- O60.57%
Isotope pattern
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
- -0.89 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- 0.1 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.3 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 132.07
- log P ≤ 5 (Crippen): -0.89
- H-bond donors ≤ 5: 2
- 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
Danger
Most widely reported: 61 company reports to ECHA. Source [1].
- Corrosive
- Harmful or irritant
- H314Causes severe skin burns and eye damage (88.5% of reports)
- H319Causes serious eye irritation (11.5% of reports)
Precautionary statements: P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P321, P337+P317, P363, P405, P501
Safety data sheets on the supplier’s page: AKos Consulting & Solutions, VladaChem, MolCore.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Varian · 500 MHz · Water) · Human Metabolome Database (HMDB) (Bruker · 800 MHz · Sodium phosphate (pH 7.4) in 90% H2O /10% D2O)
- 13C NMRSpectraBase (Varian FT-80)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water) · Human Metabolome Database (HMDB) (Bruker · 800 MHz)
- GC-MSHuman Metabolome Database (HMDB) (GC-MS) · Human Metabolome Database (HMDB) (GC-MS) · Human Metabolome Database (HMDB) (GC-MS) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) · Positive) · MassBank of North America (MoNA) (GC-MS)
- MS-MSHuman Metabolome Database (HMDB) (QTOF · positive) · Human Metabolome Database (HMDB) (QTOF · positive) · Human Metabolome Database (HMDB) (QTOF · positive) · Human Metabolome Database (HMDB) (QTOF · positive) · Human Metabolome Database (HMDB) (QTOF · positive) · Human Metabolome Database (HMDB) (QTOF · positive)
- LC-MSMassBank Europe (impact II · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank Europe (TQD, Waters · LC-ESI-QQ · POSITIVE) · MassBank of North America (MoNA) (Quattro_QQQ · negative) · MassBank of North America (MoNA) (Quattro_QQQ · negative) · MassBank of North America (MoNA) (Quattro_QQQ · negative)
- Other MSMassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI) · MassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI)
- UV-VISSpectraBase
- FTIRSpectraBase (KBr WAFER)
- ATR-IRSpectraBase (Bio-Rad FTS · ATR-Neat (DuraSamplIR II))
- RamanSpectraBase (FT-Raman)
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]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.