Showing Compound Phosphohydroxypyruvic acid (FDB022377)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:01 UTC

Update date

2020-09-17 15:40:30 UTC

Primary ID

FDB022377

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phosphohydroxypyruvic acid

Description

Phosphohydroxypyruvic acid, also known as 3-phosphooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. Phosphohydroxypyruvic acid is a moderately acidic compound (based on its pKa). Phosphohydroxypyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid through the action of the enzyme D-3-phosphoglycerate dehydrogenase. In addition, phosphohydroxypyruvic acid and L-glutamic acid can be converted into phosphoserine and oxoglutaric acid through its interaction with the enzyme phosphoserine aminotransferase. In humans, phosphohydroxypyruvic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. A carboxyalkyl phosphate that is pyruvic acid substituted at position 3 by a 3-phosphonooxy group.

CAS Number

3913-50-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
3-Phosphohydroxypyruvic acid	ChEBI
Hydroxypyruvic acid phosphate	ChEBI
3-Phosphonooxypyruvic acid	Kegg
3-Phosphohydroxypyruvate	Kegg
3-Phosphooxypyruvate	Kegg
Hydroxypyruvate phosphate	Generator
Hydroxypyruvic acid phosphoric acid	Generator
3-Phosphonooxypyruvate	Generator
3-Phosphooxypyruvic acid	Generator
Phosphohydroxypyruvate	Generator
2-oxo-3-(Phosphonooxy)-propanoate	HMDB
2-oxo-3-(Phosphonooxy)-propanoic acid	HMDB
3-Phosphonatooxypyruvate	HMDB
2-Oxo-3-(phosphonooxy)propanoic acid	HMDB
2-Oxo-3-(phosphonooxy)propionic acid	HMDB
Phosphohydroxypyruvic acid	HMDB
2-oxo-3-(Onooxy)-propanoate	HMDB
2-oxo-3-(Onooxy)-propanoic acid	HMDB
2-oxo-3-(phosphonooxy)-Propanoate	hmdb
2-oxo-3-(phosphonooxy)-Propanoic acid	hmdb
3-Ohydroxypyruvate	Generator
3-Ohydroxypyruvic acid	ChEBI
3-Onatooxypyruvate	HMDB
3-Onooxypyruvate	Generator
3-Onooxypyruvic acid	ChEBI
Hydroxypyruvate ate	Generator
Hydroxypyruvic acid ate	ChEBI
Hydroxypyruvic acid ic acid	Generator
Ohydroxypyruvate	Generator
Ohydroxypyruvic acid	ChEBI
phosphohydroxypyruvic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	13.4 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-0.87	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.02	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	30.56 m³·mol⁻¹	ChemAxon
Polarizability	12.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H5O7P

IUPAC name

2-oxo-3-(phosphonooxy)propanoic acid

InChI Identifier

InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)

InChI Key

LFLUCDOSQPJJBE-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C(=O)COP(O)(O)=O

Average Molecular Weight

184.0414

Monoisotopic Molecular Weight

183.977289026

Classification

Description

Belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Glycerone phosphates

Alternative Parents

Substituents

Glycerone phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Monosaccharide
Keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxyalkyl phosphate (CHEBI:30933 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Phosphohydroxypyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9300000000-33ff06735f8214248ea3	Spectrum
Predicted GC-MS	Phosphohydroxypyruvic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-9510000000-f67b2feb11cbb37fdf47	Spectrum
Predicted GC-MS	Phosphohydroxypyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-4411ba8f6713e6b68f94	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00s9-0900000000-457227604cff5cdecb73	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g0-6900000000-5ced177e050ba3272f0f	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-3900000000-22820af5ec79da81207b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-0127ef53c9426c592779	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-4ba77bd112070310c576	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-1900000000-0d44a3e3fb04adf7390b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9400000000-29a2afefebab0a9dc88b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0016-9000000000-2f054e3a4d1b04f903f2	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9500000000-d989c4c4b7671c11809a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-7e6d85bfb63dfb4e3ea0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-25	View Spectrum