MiMeDB: Showing metabocard for Propanoyl phosphate (MMDBc0030088)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:53:28 UTC

Update Date

2022-08-31 17:39:37 UTC

Metabolite ID

MMDBc0030088

Metabolite Identification

Common Name

Propanoyl phosphate

Description

Propanoyl phosphate is an alkylphosphate. It is generated during the course of threonine degradation via propanoyl-CoA. The first reaction in the anaerobic threonine dehydratase pathway is catalyzed by catabolic threonine dehydratase which degrades threonine to 2-oxobutanoate (alpha-ketobutyrate) and ammonia. The 2-oxobutanoate then undergoes lyase cleavage with the addition of coenzyme A to form propanoyl-CoA and formate. Once propanoyl-CoA is formed, it is processed via propionyl-phosphate to propionate in a reaction sequence that produces ATP. Acetate kinase AckA can also utilize propionate as a substrate in the final reaction. The enzymes in this pathway are also able to process L-serine, with pyruvate as the final product [EcoCyc].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Propanoyloxy)phosphonate(2-)	ChEBI
Propanoyl phosphate dianion	ChEBI
(Propanoyloxy)phosphonic acid(2-)	Generator
Propanoyl phosphoric acid dianion	Generator
Propanoyl phosphoric acid	Generator

Molecular Formula

C₃H₅O₅P

Average Mass

152.043

Monoisotopic Mass

151.988557419

IUPAC Name

(propanoyloxy)phosphonate

Traditional Name

propanoyl phosphate

CAS Registry Number

121-69-7

SMILES

CCC(=O)OP([O-])([O-])=O

InChI Identifier

InChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2

InChI Key

FMNMEQSRDWIBFO-UHFFFAOYSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Acyl monophosphates

Alternative Parents

Substituents

Acyl monophosphate
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58933 )
a small molecule (PROPIONYL-P )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	37.6 g/L	ALOGPS
logP	0.01	ALOGPS
logP	-0.18	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.19 m³·mol⁻¹	ChemAxon
Polarizability	11.2 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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007535	ADP	Adenosine triphosphate	Not Available	Propionate kinase	VMH	30371894
MMDBr0007550	Phosphate	Coenzyme A	Not Available	Phosphate acetyltransferase	VMH	30371894
MMDBr0014297	Adenosine triphosphate	ADP	Propionate kinase	Phosphorylation	RHEA	34755880
MMDBr0014768	Phosphate	CoA	Phosphate propanoyltransferase	N-Acetylation	RHEA	34755880
MMDBr0014769	Phosphate	CoA	Phosphate propanoyltransferase	Transfer of a propanoyl group	RHEA	34755880
MMDBr0014770	CoA	Phosphate	Phosphate propanoyltransferase	Transfer of a propanoyl group	RHEA	34755880
MMDBr0018583	Propionyl-CoA	Coenzyme A	Phosphate acetyltransferase	N-Acetylation	PathBank	31602464
MMDBr0018584	Propanoyl phosphate	Propionic acid	Acetate kinase	Phosphorylation	PathBank	31602464

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	Proteobacteria	177	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	367	Human feces; Human pleural fluid plaque; Pig ; Human ; Human stool; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Actinobacteria	114	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	112	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Thermotogae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22003434

PDB ID

Not Available

ChEBI ID

58933

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Propanoyl phosphate (MMDBc0030088)

MOL for #<Metabolite:0x0000564af07e68a0>

3D MOL for #<Metabolite:0x0000564af07e68a0>

3D SDF for #<Metabolite:0x0000564af07e68a0>

3D-SDF for #<Metabolite:0x0000564af07e68a0>

PDB for #<Metabolite:0x0000564af07e68a0>

3D PDB for #<Metabolite:0x0000564af07e68a0>

SMILES for #<Metabolite:0x0000564af07e68a0>

INCHI for #<Metabolite:0x0000564af07e68a0>

Structure for #<Metabolite:0x0000564af07e68a0>

3D Structure for #<Metabolite:0x0000564af07e68a0>