MiMeDB: Showing metabocard for Carboxyphosphate (MMDBc0031968)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:56:55 UTC

Update Date

2025-11-05 17:12:59 UTC

Metabolite ID

MMDBc0031968

Metabolite Identification

Common Name

Carboxyphosphate

Description

Carboxyphosphate is a chemical intermediate classified as a phosphate ester. It plays a crucial role in biochemical pathways, particularly in ATP-dependent carboxylases, where it is proposed to function as an intermediate during the carboxylation of substrates. Although carboxyphosphate has not been directly isolated or observed experimentally (PMID:25405523 ), computational studies suggest that it can exist as either a monoanion or dianion, adopting a novel pseudochair conformation characterized by an intramolecular charge-assisted hydrogen bond (CAHB) (PMID:25405523 ). This unique conformation is significant in understanding the catalytic mechanism of enzymes like biotin carboxylase, where carboxyphosphate is involved in the transfer of CO₂ to biotin (PMID:26020841 ). High-resolution crystal structures have provided insights into the binding interactions and transition states associated with carboxyphosphate, indicating that it stabilizes a tetrahedral dianionic transition state during catalysis (PMID:26020841 ). Furthermore, the CHARMM force field has been utilized to analyze the energetic properties of carboxyphosphate, revealing significant differential contributions to the CAHB strength between its closed and open forms (PMID:25405523 ). Overall, these findings enhance our understanding of carboxyphosphate's role in enzymatic reactions involving carboxylation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Carbonic acid, monoanhydride with phosphoric acid	ChEBI
Carbonic-phosphoric anhydride	ChEBI
Carboxy phosphate	ChEBI
Carbonate, monoanhydride with phosphate	Generator
Carboxy phosphoric acid	Generator
Carboxyphosphoric acid	Generator
Carbonic acid, monoanhydride with phosphoric acid, ion(2-)	MeSH
Carboxyphosphate	MeSH

Molecular Formula

CH₃O₆P

Average Mass

142.003

Monoisotopic Mass

141.966724815

IUPAC Name

(carboxyoxy)phosphonic acid

Traditional Name

carboxyoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

OC(=O)OP(O)(O)=O

InChI Identifier

InChI=1S/CH3O6P/c2-1(3)7-8(4,5)6/h(H,2,3)(H2,4,5,6)

InChI Key

LQQCGEGRINLHDP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic phosphoric acids and derivatives. These are organic compounds containing phosphoric acid or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Not Available

Direct Parent

Organic phosphoric acids and derivatives

Alternative Parents

Substituents

Organic phosphoric acid derivative
Carbonic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	12.5 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-0.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.19	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	20.66 m³·mol⁻¹	ChemAxon
Polarizability	8.65 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-8900000000-91cd1bd8db20d4c76f86	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-1090227de7fb90e690e4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9000000000-0c83a0c51f343d4f7dda	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9100000000-e5e3900a6ec7fe53ef32	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-9997b83bf2d4f914bdc1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d4a56ece1e7d450beb01	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (retained)	2025-10-23	486.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	367.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	39.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (void)	2025-10-23	258.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	275.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	346.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	475.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	748.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	773.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	230.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	368.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	253.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	73.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	402.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	698.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	103.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	335.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	590.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	555.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Carboxyphosphate_TMS_1	C[Si](C)(C)OC(=O)OP(=O)(O)O	standard non polar	2025-10-24	1628.84
Gas Chromatography	Carboxyphosphate_TMS_2	C[Si](C)(C)OP(=O)(O)OC(=O)O	standard non polar	2025-10-24	2187.37
Gas Chromatography	Carboxyphosphate_TMS_3	C[Si](C)(C)OC(=O)OP(=O)(O)O[Si](C)(C)C	standard non polar	2025-10-24	1870.74
Gas Chromatography	Carboxyphosphate_TMS_4	C[Si](C)(C)OP(=O)(OC(=O)O)O[Si](C)(C)C	standard non polar	2025-10-24	1600.12
Gas Chromatography	Carboxyphosphate_TMS_5	C[Si](C)(C)OC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1774.88
Gas Chromatography	Carboxyphosphate_TMS_1	C[Si](C)(C)OC(=O)OP(=O)(O)O	standard polar	2025-10-24	1996.42
Gas Chromatography	Carboxyphosphate_TMS_2	C[Si](C)(C)OP(=O)(O)OC(=O)O	standard polar	2025-10-24	2200.82
Gas Chromatography	Carboxyphosphate_TMS_3	C[Si](C)(C)OC(=O)OP(=O)(O)O[Si](C)(C)C	standard polar	2025-10-24	1891.96
Gas Chromatography	Carboxyphosphate_TMS_4	C[Si](C)(C)OP(=O)(OC(=O)O)O[Si](C)(C)C	standard polar	2025-10-24	1894.01
Gas Chromatography	Carboxyphosphate_TMS_5	C[Si](C)(C)OC(=O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2367.1

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-18238

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

195870

PDB ID

Not Available

ChEBI ID

90099

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for Carboxyphosphate (MMDBc0031968)

MOL for #<Metabolite:0x00007f9ace2f3df0>

3D MOL for #<Metabolite:0x00007f9ace2f3df0>

3D SDF for #<Metabolite:0x00007f9ace2f3df0>

3D-SDF for #<Metabolite:0x00007f9ace2f3df0>

PDB for #<Metabolite:0x00007f9ace2f3df0>

3D PDB for #<Metabolite:0x00007f9ace2f3df0>

SMILES for #<Metabolite:0x00007f9ace2f3df0>

INCHI for #<Metabolite:0x00007f9ace2f3df0>

Structure for #<Metabolite:0x00007f9ace2f3df0>

3D Structure for #<Metabolite:0x00007f9ace2f3df0>