ECMDB: Pantothenic acid (ECMDB00210) (M2MDB000085)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)Transporters (5)XML

Proteins (803)

Record Information

Version

2.0

Creation Date

2012-05-31 10:23:43 -0600

Update Date

2015-09-13 12:56:06 -0600

Secondary Accession Numbers

ECMDB00210

Identification

Name:

Pantothenic acid

Description

Pantothenic acid, also called vitamin B5, is a water-soluble vitamin required to sustain life. Pantothenic acid is needed to form coenzyme-A (CoA), and is thus critical in the metabolism and synthesis of carbohydrates, proteins, and fats. Its name is derived from the Greek pantothen meaning "from everywhere" and small quantities of pantothenic acid are found in nearly every food, with high amounts in whole grain cereals, legumes, eggs, meat, and royal jelly.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(+)-Pantothenate
(+)-Pantothenic acid
(R)-pantothenic acid
(D)-(+)-Pantothenate
(D)-(+)-Pantothenic acid
(R)-pantothenate
(R)-pantothenic acid
Chick antidermatitis factor
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-β-alanine
D-Pantothenate
D-Pantothenic acid
Delta-Pantothenate
Delta-Pantothenic acid
Pantothenate
Vitamin B5
Vitamin B₅
δ-Pantothenate
δ-Pantothenic acid

Chemical Formula:

C₉H₁₇NO₅

Weight:

Average: 219.235
Monoisotopic: 219.110672659

InChI Key:

GHOKWGTUZJEAQD-UHFFFAOYSA-N

InChI:

InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)

CAS number:

79-83-4

IUPAC Name:

3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid

Traditional IUPAC Name:

(+)-pantothenic acid

SMILES:

CC(C)(CO)C(O)C(=O)NCCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carbonyl group
Primary alcohol
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pantothenic acid (CHEBI:46905 )
Water-soluble vitamins (C00864 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

< 25 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	1000.0 mg/mL [MERCK INDEX (1996)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	60.5 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.4	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	51.51 m³·mol⁻¹	ChemAxon
Polarizability	21.99 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:

SMPDB Pathways:

Pantothenate and CoA biosynthesis	PW000828
beta-Alanine metabolism	PW000896

KEGG Pathways:

Metabolic pathways eco01100
Pantothenate and CoA biosynthesis ec00770
beta-Alanine metabolism ec00410

EcoCyc Pathways:

phosphopantothenate biosynthesis I PANTO-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0zfu-1950000000-e17ccf50735fd5171fc4	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0f6t-3921000000-6a2222a87b5ffd328cee	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0920000000-9785638e8fe83ade2497	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0zfr-0920000000-5f3d78d9671cf3e9e436	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0910000000-1ad24073d09589d69733	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-8910000000-e9fba0c36e325b52e91f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00fs-9665200000-38141a3794d53c37aba5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0090000000-4077cb3290a3d501c967	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000j-9520000000-21cefac627d830ed5bbf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000j-9400000000-d7cac2e845877b5d4c45	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-a56de6ea4cc94ead9287	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-958b1047fc59d5fa55ab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-9100000000-5cf3012f98b80b72b87c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00ks-9330000000-5220625c440a0e4d0e1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00ks-9330000000-da413d79b085b05c74fa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000j-9410000000-e4934ca5cda48554f8bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-0090000000-d74155da6ca6fff432c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9560000000-663aa7cea0b521907df1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-006x-9200000000-475c18425c9352988ee1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01bc-9000000000-afcfa162e86332d3cfa2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-421f28522574e5fa8eae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0f6x-9470000000-cfd10935dbbb59770f3f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0090000000-460a4bec2421708c0e18	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-2190000000-6eec23d0d7031fc1e28b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dl-9460000000-a6391c9eace085a7cd68	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-006x-9450000000-f677ff82e7d7f3f58ba1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fe0-9230000000-5d3b471f56b2c2e5535b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9200000000-12b30ec690e561fbee15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-167b8eb76324b5c3850a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-3790000000-e2e626db270df267d7db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-7910000000-01cff3f952409e9e9550	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-a56f834482e2844f6924	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. Pubmed: 182198
Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7. Pubmed: 3788840
Fry PC, Fox HM, Tao HG: Metabolic response to a pantothenic acid deficient diet in humans. J Nutr Sci Vitaminol (Tokyo). 1976;22(4):339-46. Pubmed: 1011047
Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6. Pubmed: 2499220
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
Loftus EV Jr, Tremaine WJ, Nelson RA, Shoemaker JD, Sandborn WJ, Phillips SF, Hasan Y: Dexpanthenol enemas in ulcerative colitis: a pilot study. Mayo Clin Proc. 1997 Jul;72(7):616-20. Pubmed: 9212762
Preibisz J, Chlewicka I: [Digitalis treatment in acute myocardial infarct. Determination of serum drug levels] Pol Arch Med Wewn. 1977 Dec;58(6):585-91. Pubmed: 600836
Roth-Maier DA, Wauer A, Stangl GI, Kirchgessner M: Precaecal digestibility of niacin and pantothenic acid from different foods. Int J Vitam Nutr Res. 2000 Jan;70(1):8-13. Pubmed: 10683755
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
Srinivasan V, Christensen N, Wyse BW, Hansen RG: Pantothenic acid nutritional status in the elderly--institutionalized and noninstitutionalized. Am J Clin Nutr. 1981 Sep;34(9):1736-42. Pubmed: 7025609
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:

Kataoka, Michihiko; Shimizu, Sakayu; Doi, Yukiko; Yamada, Hideaki. Stereospecific reduction of ethyl 2'-ketopantothenate to ethyl D-(+)-pantothenate with microbial cells as a catalyst. Applied and Environmental Microbiology (1990), 56(11), 3595-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16454
HMDB ID	HMDB00210
Pubchem Compound ID	6613
Kegg ID	C00864
ChemSpider ID	963
Wikipedia	Pantothenic acid
BioCyc ID	PANTOTHENATE
EcoCyc ID	PANTOTHENATE

Enzymes

Protein Details

1. Pantothenate kinase

General function:: Involved in pantothenate kinase activity
Specific function:: ATP + (R)-pantothenate = ADP + (R)-4'- phosphopantothenate
Gene Name:: coaA
Uniprot ID:: P0A6I3
Molecular weight:: 36359

Reactions

ATP + (R)-pantothenate = ADP + (R)-4'-phosphopantothenate.

Protein Details

2. Pantothenate synthetase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the condensation of pantoate with beta-alanine in an ATP-dependent reaction via a pantoyl-adenylate intermediate
Gene Name:: panC
Uniprot ID:: P31663
Molecular weight:: 31597

Reactions

ATP + (R)-pantoate + beta-alanine = AMP + diphosphate + (R)-pantothenate.

Transporters

Protein Details

1. Sodium/pantothenate symporter

General function:: Involved in sodium ion transmembrane transporter activity
Specific function:: Catalyzes the sodium-dependent uptake of extracellular pantothenate
Gene Name:: panF
Uniprot ID:: P16256
Molecular weight:: 51717

Protein Details

2. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

3. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

4. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

5. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Pantothenic acid (ECMDB00210) (M2MDB000085)

Structure for #<Compound:0xa2de225c>

Enzymes

Reactions

Reactions

Transporters