Showing Compound 2,3-Diphosphoglyceric acid (FDB022538)

Record Information

Version

1.0

Creation date

2011-09-21 00:15:33 UTC

Update date

2020-09-17 15:38:54 UTC

Primary ID

FDB022538

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2,3-Diphosphoglyceric acid

Description

2,3-Diphosphoglyceric acid, also known as 2,3-disphospho-D-glycerate or DPG, 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. The D-enantiomer of 2,3-bisphosphoglyceric acid. 2,3-Diphosphoglyceric acid is an extremely strong acidic compound (based on its pKa). 2,3-Diphosphoglyceric acid exists in all living species, ranging from bacteria to humans. Within humans, 2,3-diphosphoglyceric acid participates in a number of enzymatic reactions. In particular, 2,3-diphosphoglyceric acid can be biosynthesized from glyceric acid 1,3-biphosphate; which is catalyzed by the enzyme bisphosphoglycerate mutase. In addition, 2,3-diphosphoglyceric acid can be converted into 3-phosphoglyceric acid; which is catalyzed by the enzyme bisphosphoglycerate mutase. In humans, 2,3-diphosphoglyceric acid is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway.

CAS Number

138-81-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2R)-2,3-Bis(onooxy)-propanoate	HMDB
(2R)-2,3-Bis(onooxy)-propanoic acid	HMDB
(2R)-2,3-Bis(phosphonooxy)-propanoate	HMDB
(2R)-2,3-bis(phosphonooxy)-Propanoate	hmdb
(2R)-2,3-Bis(phosphonooxy)-propanoic acid	HMDB
(2R)-2,3-bis(phosphonooxy)-Propanoic acid	hmdb
(2R)-2,3-Bis(phosphonooxy)propanoic acid	HMDB
(2R)-2,3-Bis(phosphonooxy)propionic acid	HMDB
(R)-2,3-Bis(onooxy)-propanoate	HMDB
(R)-2,3-Bis(onooxy)-propanoic acid	HMDB

Showing 1 to 10 of 73 entries

Predicted Properties

Property	Value	Source
Water Solubility	9.69 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.8	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	0.48	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.13 m³·mol⁻¹	ChemAxon
Polarizability	17.96 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

C3H8O10P2

IUPAC name

(2R)-2,3-bis(phosphonooxy)propanoic acid

InChI Identifier

InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1

InChI Key

XOHUEYCVLUUEJJ-UWTATZPHSA-N

Isomeric SMILES

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

Average Molecular Weight

266.0371

Monoisotopic Molecular Weight

265.9592695

Classification

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

Monoalkyl phosphate
Glyceric_acid
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Monosaccharide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2,3-bisphosphoglyceric acid (CHEBI:17720 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Cell and elements:

Cell:

Organ and components:

Testicle

Subcellular:

Biofluid and excreta:

Blood

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	2,3-Diphosphoglyceric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9320000000-fbd8c78fd88d592fab56	Spectrum
Predicted GC-MS	2,3-Diphosphoglyceric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-9410000000-ea4c253779009c08e1bd	Spectrum
Predicted GC-MS	2,3-Diphosphoglyceric 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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0930000000-5127f7f7568a961a8078	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-2900000000-e9e3c8a32ece4b7f9fce	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-006t-9300000000-e09861cf36df495519f6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0090000000-4a9ded352d5912810741	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-066r-1960000000-0d244402e55e5ef9de1d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0ar0-5960000000-1d5a4352115c6c5eb82f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-056r-9330000000-70ae76c58e470fe3b594	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9100000000-6cacbc2756ef980dc5a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00xr-6910000000-871a376b75658c914a1e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00xr-9200000000-ab1b55ce1ad971f1b3f8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-016r-9100000000-2af5a77daca9f7cef852	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9100000000-1d6a9786ab78002b7ac2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0090000000-4a9ded352d5912810741	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-066r-1960000000-fcab8021959f67dc5a44	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ar0-5960000000-1d5a4352115c6c5eb82f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-056r-9330000000-70ae76c58e470fe3b594	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9100000000-37f228e9721638e33212	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0uxr-1490000000-ddf502cfcfd4ff0bca0b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1930000000-6b2743652b0e2aa81960	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00r2-8890000000-64b460dbcc7be6d3e820	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-6900000000-7cbb7d86341bbdc1500a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-5090000000-73e5bca24796a45bebaf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-a07defbdfd47a3f23225	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9f9abb79cd423f7b15f0	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

161681

ChEMBL ID

Not Available

KEGG Compound ID

C01159

Pubchem Compound ID

186004

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01294

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

1315507

KNApSAcK ID

Not Available

HET ID

DG2

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Bisphosphoglycerate mutase	BPGM	P07738
Multiple inositol polyphosphate phosphatase 1	MINPP1	Q9UNW1
Phosphoglycerate mutase 1	PGAM1	P18669
Phosphoglycerate mutase 2	PGAM2	P15259
Probable phosphoglycerate mutase 4	PGAM4	Q8N0Y7