Cannabis Compound Database: Showing Compound Card for 2-Phospho-D-glyceric acid (CDB004956)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:54:20 UTC

Updated at

2020-11-18 16:39:06 UTC

CannabisDB ID

CDB004956

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Phospho-D-glyceric acid

Description

2-Phospho-D-glyceric acid, also known as 2-phospho-D-glycerate or D-glycerate 2-phosphate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2-Phospho-D-glyceric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phospho-D-glyceric acid exists in all living species, ranging from bacteria to humans. Within humans, 2-phospho-D-glyceric acid participates in a number of enzymatic reactions. In particular, 2-phospho-D-glyceric acid can be biosynthesized from 3-phosphoglyceric acid; which is mediated by the enzyme phosphoglycerate mutase 2. In addition, 2-phospho-D-glyceric acid can be converted into phosphoenolpyruvic acid through the action of the enzyme Alpha-enolase. In humans, 2-phospho-D-glyceric acid is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Outside of the human body, 2-Phospho-D-glyceric acid has been detected, but not quantified in, rices. This could make 2-phospho-D-glyceric acid a potential biomarker for the consumption of these foods. A 2-Phospho-D-glyceric acid in which the glyceric acid moiety has D (R) configuration. 2-Phospho-D-glyceric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Phospho-D-glycerate	ChEBI
2-PHOSPHOGLYCERIC ACID	ChEBI
D-Glycerate 2-phosphate	ChEBI
2-Phospho-(R)-glycerate	Kegg
2-PHOSPHOGLYCERate	Generator
D-Glyceric acid 2-phosphoric acid	Generator
2-Phospho-(R)-glyceric acid	Generator
(2R)-3-Hydroxy-2-(phosphonooxy)propanoate	HMDB
(2R)-3-Hydroxy-2-(phosphonooxy)propanoic acid	HMDB
3-D-Hydroxy-2-phosphonooxy-propanoate	HMDB
3-D-Hydroxy-2-phosphonooxy-propanoic acid	HMDB
D-(+)-2-Phosphoglyceric acid	HMDB
D-2-Phosphoglyceric acid	HMDB
D-Glyceric acid 2-phosphate	HMDB
2-Phospho-D-glyceric acid	HMDB

Chemical Formula

C₃H₇O₇P

Average Molecular Weight

186.06

Monoisotopic Molecular Weight

185.9929

IUPAC Name

(2R)-3-hydroxy-2-(phosphonooxy)propanoic acid

Traditional Name

(+-)-2-phosphoglycerate

CAS Registry Number

3443-57-0

SMILES

OC[C@@H](OP(O)(O)=O)C(O)=O

InChI Identifier

InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)/t2-/m1/s1

InChI Key

GXIURPTVHJPJLF-UWTATZPHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Glyceric_acid
Monoalkyl phosphate
Hydroxy acid
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-phosphoglyceric acid (CHEBI:17835 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-1.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	0.81	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.26 m³·mol⁻¹	ChemAxon
Polarizability	13.36 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	2-Phospho-D-glyceric acid, 4 TMS, GC-MS Spectrum	splash10-014j-1986100000-67b36247ae0c01d6630f	Spectrum
GC-MS	2-Phospho-D-glyceric acid, non-derivatized, GC-MS Spectrum	splash10-014j-1986100000-67b36247ae0c01d6630f	Spectrum
Predicted GC-MS	2-Phospho-D-glyceric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9200000000-8ec7a644e48af8fc9f44	Spectrum
Predicted GC-MS	2-Phospho-D-glyceric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9030000000-cc4abc5e01c64cff2d87	Spectrum
Predicted GC-MS	2-Phospho-D-glyceric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-80caf2498862e856c8fc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-1518e606c03a8697d1b9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-66ec419add3cb3e1fd32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-b7f464912df9166dc597	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-d09faea5291df7a04b70	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-0900000000-09027263f64d0e1059c6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-1900000000-8eeb1d2a8432d1e44448	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f6t-8900000000-3b714e664b948f61ac7e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0023-9000000000-ed83591fbfd15323cd6d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001m-9000000000-39cdf9729f381069e45f	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-9300000000-24ac9683b32428f58197	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9600000000-b12281d6d89eef904e6b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-a07c4a51c820b32ec8bd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-516a86a1a17689399892	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9500000000-b33f3e08e2e8b3d5aed5	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-07016cc3ecca7d5e323b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-e2aa0f15a5d31307fa1e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2900000000-e1c96e130069d9cf375a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-91835bf01523e3aceb24	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-9000000000-d48b603841c58b435069	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycolysis
Gluconeogenesis
Glycogenosis, Type VII. Tarui disease		Not Available
Fanconi-bickel syndrome		Not Available
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bisphosphoglycerate mutase	BPGM	7q33	P07738	details
Phosphoglycerate mutase 2	PGAM2	7p13-p12	P15259	details
Probable phosphoglycerate mutase 4	PGAM4	Xq13	Q8N0Y7	details
Phosphoglycerate mutase 1	PGAM1	10q25.3	P18669	details
Beta-enolase	ENO3	17pter-p11	P13929	details
Gamma-enolase	ENO2	12p13	P09104	details
Alpha-enolase	ENO1	1p36.2	P06733	details
Multiple inositol polyphosphate phosphatase 1	MINPP1	10q23	Q9UNW1	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Beta-enolase	ENO3	17pter-p11	P13929	details
Gamma-enolase	ENO2	12p13	P09104	details
Alpha-enolase	ENO1	1p36.2	P06733	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Gamma-enolase	ENO2	12p13	P09104	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-enolase	ENO1	1p36.2	P06733	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0003391

DrugBank ID

DB01709

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6915

PubChem Compound

439278

PDB ID

Not Available

ChEBI ID

17835

References

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Bisphosphoglycerate mutase

General function:: Involved in catalytic activity
Specific function:: Plays a major role in regulating hemoglobin oxygen affinity by controlling the levels of its allosteric effector 2,3-bisphosphoglycerate (2,3-BPG). Also exhibits mutase (EC 5.4.2.1) and phosphatase (EC 3.1.3.13) activities.
Gene Name:: BPGM
Uniprot ID:: P07738
Molecular weight:: 30004.98

Enzyme Details

2. Phosphoglycerate mutase 2

General function:: Involved in catalytic activity
Specific function:: Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:: PGAM2
Uniprot ID:: P15259
Molecular weight:: 28765.96

Enzyme Details

3. Probable phosphoglycerate mutase 4

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PGAM4
Uniprot ID:: Q8N0Y7
Molecular weight:: 28776.605

Enzyme Details

4. Phosphoglycerate mutase 1

General function:: Involved in catalytic activity
Specific function:: Interconversion of 3- and 2-phosphoglycerate with 2,3-bisphosphoglycerate as the primer of the reaction. Can also catalyze the reaction of EC 5.4.2.4 (synthase) and EC 3.1.3.13 (phosphatase), but with a reduced activity.
Gene Name:: PGAM1
Uniprot ID:: P18669
Molecular weight:: 28803.675

Enzyme Details

5. Beta-enolase

General function:: Involved in magnesium ion binding
Specific function:: Appears to have a function in striated muscle development and regeneration.
Gene Name:: ENO3
Uniprot ID:: P13929
Molecular weight:: 42248.03

Enzyme Details

6. Gamma-enolase

General function:: Involved in magnesium ion binding
Specific function:: Has neurotrophic and neuroprotective properties on a broad spectrum of central nervous system (CNS) neurons. Binds, in a calcium-dependent manner, to cultured neocortical neurons and promotes cell survival (By similarity).
Gene Name:: ENO2
Uniprot ID:: P09104
Molecular weight:: 47268.125

Enzyme Details

7. Alpha-enolase

General function:: Involved in magnesium ion binding
Specific function:: Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production. MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
Gene Name:: ENO1
Uniprot ID:: P06733
Molecular weight:: 36927.84

Enzyme Details

8. Multiple inositol polyphosphate phosphatase 1

General function:: Involved in acid phosphatase activity
Specific function:: Acts as a phosphoinositide 5- and phosphoinositide 6-phosphatase and regulates cellular levels of inositol pentakisphosphate (InsP5) and inositol hexakisphosphate (InsP6). Also acts as a 2,3-bisphosphoglycerate 3-phosphatase, by mediating the dephosphorylation of 2,3-bisphosphoglycerate (2,3-BPG) to produce phospho-D-glycerate without formation of 3-phosphoglycerate. May play a role in bone development (endochondral ossification).
Gene Name:: MINPP1
Uniprot ID:: Q9UNW1
Molecular weight:: 34660.555

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for 2-Phospho-D-glyceric acid (CDB004956)

Structure for CDB004956 (2-Phospho-D-glyceric acid)

Enzymes