Phosphoenolpyruvate
Athanor · official
C3H5O6P · 168.04 g/mol
IUPAC name: 2-phosphonooxyprop-2-enoic acid
Also called PEP, phosphoenolpyruvic acid
Names and identifiers
- IUPAC name
- 2-phosphonooxyprop-2-enoic acid
- Synonyms
- PEP, phosphoenolpyruvic acid, Phosphoenolpyruvic acid
+ 36 more
2-(phosphonooxy)prop-2-enoic acid, 2-Phosphonooxyprop-2-enoic acid, 2-(phosphonooxy)-2-propenoic acid, 545YL308OW, 2-(phosphonooxy)-2-propenoate, CHEBI:44897, DTXSID80861797, CHEBI:18021, DTXSID00223277, RefChem:173566, DTXCID00145768, DTXCID90197579, 1-carboxyethenoxy(oxonio)phosphinate, 2-(hydroxy(oxonio)phosphoryl)oxyprop-2-enoate, 200-804-3, 2-Propenoic acid, 2-(phosphonooxy)-, 2-Dihydroxyphosphinoyloxyacrylic acid, Phosphopyruvic acid, 2-(Phosphonooxy)acrylic acid, P-enol-pyruvate, C3H5O6P, P-enolpyruvate, UNII-545YL308OW, 1nhx, EINECS 205-312-2, Phosphoenol pyruvic acid, bmse000107, Acrylic acid, 2-hydroxy-, dihydrogen phosphate, SCHEMBL7908, GTPL4692, CHEMBL1235228, propenoic acid, 2-phosphonooxy-, 2-PHOSPHOENOLPYRUVIC ACID, 2-(phosphonooxy)prop-2-enoicacid, BDBM50366413, EBC-44181
- Molecular formula
- C3H5O6P
- Empirical formula
- C3H5O6P
- Molecular weight
- 168.04 g/mol
- Exact mass
- 167.98237
- CAS number
- 138-08-9
- PubChem CID
- 1005
- Canonical SMILES
- C=C(C(=O)O)OP(=O)(O)O
- Isomeric SMILES
- C=C(C(=O)O)OP(=O)(O)O
- InChI
- InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
- InChIKey
- DTBNBXWJWCWCIK-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 10
- Rings
- 0
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0
- H-bond donors
- 3
- H-bond acceptors
- 3 computed here · PubChem 6
- Rotatable bonds
- 3
- TPSA (Ų)
- 104.1 computed here · PubChem 104
- Formal charge
- 0
- XLogP3
- -1.1 PubChem
- Complexity
- 201 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
- C21.44%
- H3.00%
- O57.13%
- P18.43%
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
- -0.31 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.49 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.26 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 168.04
- log P ≤ 5 (Crippen): -0.31
- 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
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: Smolecule, ChemoSapiens, BLD Pharm.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Varian · 600 MHz · Water) · Human Metabolome Database (HMDB) (Bruker · D2O) · SpectraBase
- 13C NMRHuman Metabolome Database (HMDB) (Bruker · D2O) · SpectraBase
- 1H-1H NMRHuman Metabolome Database (HMDB)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- GC-MSHuman 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 Europe (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies · GC-EI-TOF · POSITIVE) · MassBank of North America (MoNA) (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies · GC-EI-TOF · positive)
- MS-MSHuman Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative)
- LC-MSMassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · NEGATIVE) · MassBank Europe (API3000, Applied Biosystems · LC-ESI-QQ · POSITIVE)
- 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) · MassBank of North America (MoNA) (ESI · negative)
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]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [3]MassBank Europe · 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
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.