MiMeDB: Showing metabocard for (R)-4'-phosphopantothenic acid (MMDBc0033113)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:35:20 UTC

Update Date

2024-04-30 20:00:31 UTC

Metabolite ID

MMDBc0033113

Metabolite Identification

Common Name

(R)-4'-phosphopantothenic acid

Description

D-4'-Phosphopantothenate 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. [Biocyc COA-PWY]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₈NO₈P

Average Mass

299.2149

Monoisotopic Mass

299.077003069

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

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)/t7-/m0/s1

InChI Key

XHFVGHPGDLDEQO-ZETCQYMHSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

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)	2025-10-24	475.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	336.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	92.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	280.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	262.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	219.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	542.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	605.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	549.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	143.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	306.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	154.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	64.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	402.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	550.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	44.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	184.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	707.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	573.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_1	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard non polar	2025-10-24	1672.56
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_2	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1918.24
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_3	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O	standard non polar	2025-10-24	1771.95
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_4	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2641.05
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_5	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2207.95
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_6	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard non polar	2025-10-24	2057.19
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_7	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1992.28
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_8	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1914.45
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_9	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1121.7
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_10	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O	standard non polar	2025-10-24	1374.81
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_11	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2796.35
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_12	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1544.76
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_13	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1242.86
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_14	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard non polar	2025-10-24	2242.65
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_15	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1744.4
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_16	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1651.29
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_17	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2175.49
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_18	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1814.51
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_19	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2001.17
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_20	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2376.98
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_21	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1818.59
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_22	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1017.72
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_23	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1788.74
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_1	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard polar	2025-10-24	1593.64
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_2	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	2144.04
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_3	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O	standard polar	2025-10-24	2161.24
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_4	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1797.87
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_5	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	2859.61
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_6	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard polar	2025-10-24	2043.57
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_7	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2118.07
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_8	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	2212.25
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_9	CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2014.36
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_10	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O	standard polar	2025-10-24	2164.7
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_11	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1621.41
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_12	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	1431.85
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_13	CC(C)(COP(=O)(O)O)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1851.36
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_14	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O	standard polar	2025-10-24	1234.73
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_15	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1722.49
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_16	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	1414.29
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_17	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2315.13
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_18	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1941.34
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_19	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)NCCC(=O)O[Si](C)(C)C	standard polar	2025-10-24	1628.17
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_20	CC(C)(COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	882.366
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_21	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1829.18
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_22	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1615.89
Gas Chromatography	(R)-4'-phosphopantothenic acid_TMS_23	CC(C)(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	854.823

Biological Properties

Cellular Locations

Mitochondria

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
MMDBp0192635	Pantothenate kinase 4	Enzyme	Q9NVE7	Homo sapiens
MMDBp0192636	Pantothenate kinase 2, mitochondrial	Unknown	Q9BZ23	Homo sapiens
MMDBp0192637	Pantothenate kinase 1	Enzyme	Q8TE04	Homo sapiens
MMDBp0192638	Pantothenate kinase 3	Enzyme	Q9H999	Homo sapiens
MMDBp0193763	Phosphopantothenate--cysteine ligase	Enzyme	Q9HAB8	Homo sapiens

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
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Firmicutes	469	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	475	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Cattle ; Sheep ; Chicken ; Turkey ; Dog	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	162	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	123	Human feces; Human appendix biopsy; Human ; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	11	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria/Eubacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	8	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Proteobacteria	4	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Cattle ; Sheep ; Chicken ; Turkey ; Dog	Metabolic reconstruction
Bacteria/Eubacteria	Acidobacteria	3
Bacteria/Eubacteria	Aquificae	3
Bacteria/Eubacteria	Chlorobi	4
Bacteria/Eubacteria	Chloroflexi	6
Bacteria/Eubacteria	Deinococcus-thermus	4
Bacteria/Eubacteria	Dictyoglomi	1
Bacteria/Eubacteria	Elusimicrobia	2
Bacteria/Eubacteria	Thermotogae	7
Bacteria/Eubacteria	Cyanobacteria	8
Bacteria	nah	1
Archaea/Archaea	Euryarchaeota	5		Metabolic reconstruction

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 ]

Showing metabocard for (R)-4'-phosphopantothenic acid (MMDBc0033113)

MOL for #<Metabolite:0x00005624ca14e408>

3D MOL for #<Metabolite:0x00005624ca14e408>

3D SDF for #<Metabolite:0x00005624ca14e408>

3D-SDF for #<Metabolite:0x00005624ca14e408>

PDB for #<Metabolite:0x00005624ca14e408>

3D PDB for #<Metabolite:0x00005624ca14e408>

SMILES for #<Metabolite:0x00005624ca14e408>

INCHI for #<Metabolite:0x00005624ca14e408>

Structure for #<Metabolite:0x00005624ca14e408>

3D Structure for #<Metabolite:0x00005624ca14e408>