P. aeruginosa Metabolome Database: D-4'-Phosphopantothenate (PAMDB000227)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000227

Identification

Name:

D-4'-Phosphopantothenate

Description:

D-4'-Phosphopantothenate is a product of the phosphorylatation of Pantothenate by Pantothenate kinase. It is an intermediate in coenzyme A (CoA) biosynthesis pathway. Coenzyme A is a cofactor of ubiquitous occurrence in plants, bacteria, and animals. It is needed in a large number of enzymatic reactions central to intermediary metabolism, including the oxidation of fatty acids, carbohydrates, and amino acids. Only plants and microorganisms like Pseudomonas aeruginosa are capable of synthesizing this compound de novo.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(R)-4'-phosphopantothenate
(R)-4'-phosphopantothenic acid
4'-P-Pantothenate
4'-P-Pantothenic acid
4'-Phosphopantothenate
4'-Phosphopantothenic acid
4'PPA
D-4'-Phosphopantothenate
D-4'-Phosphopantothenic acid

Chemical Formula:

C₉H₁₈NO₈P

Average Molecular Weight:

299.2149

Monoisotopic Molecular Weight:

299.077003069

InChI Key:

XHFVGHPGDLDEQO-UHFFFAOYSA-N

InChI:

InChI=1S/C9H18NO8P/c1-9(2,5-18-19(15,16)17)7(13)8(14)10-4-3-6(11)12/h7,13H,3-5H2,1-2H3,(H,10,14)(H,11,12)(H2,15,16,17)

CAS number:

Not Available

IUPAC Name:

3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid

Traditional IUPAC Name:

3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid

SMILES:

CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-acyl-amine
Monosaccharide
Fatty amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.09 mg/mL	ALOGPS
logP	-1.5	ALOGPS
logP	-1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.39 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	62.38 m³·mol^-1	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Metabolic pathways pae01100
Pantothenate and CoA biosynthesis pae00770
beta-Alanine metabolism pae00410

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-5392000000-359b42878651b9d9c2e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ul0-7960000000-5e1d3f9b32192536e41d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-f9de3989fd11e22afcbe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9370000000-f7d945402a704f305bba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-14a239b738777adfeee4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a3802c65fdf7fe039457	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15905
HMDB ID	HMDB01016
Pubchem Compound ID	41635
Kegg ID	C03492
ChemSpider ID	128
Wikipedia ID	Not Available
BioCyc ID	4-P-PANTOTHENATE
EcoCyc ID	4-P-PANTOTHENATE

D-4'-Phosphopantothenate (PAMDB000227)

Structure for D-4'-Phosphopantothenate (PAMDB000227)