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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-09-24 16:05:23 UTC

Update Date

2022-09-22 18:35:13 UTC

HMDB ID

HMDB0240389

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pantoic acid

Description

Pantoic acid (along with beta-alanine) is used to synthesize pantothenic acid (vitamin B5) in most microorganisms and plants. Pantothenic acid is a structural component of coenzyme A (CoA) which is involved in essential biological processes such as the citric acid cycle (TCA cycle) and the synthesis of carbohydrates, proteins, and fat. Pantothenic acid is found widespread in foods but especially in egg yolk, offal, fish, whole-grains, legumes, mushrooms, avocados, broccoli, and royal jelly (from bees).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Pantoate	ChEBI
(R)-Pantoic acid	HMDB
(R)-Pantoate	HMDB
Pantoic acid	ChEBI

Chemical Formula

C₆H₁₂O₄

Average Molecular Weight

148.1571

Monoisotopic Molecular Weight

148.073558872

IUPAC Name

(2R)-2,4-dihydroxy-3,3-dimethylbutanoic acid

Traditional Name

(R)-pantoic acid

CAS Registry Number

1112-33-0

SMILES

CC(C)(CO)[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1

InChI Key

OTOIIPJYVQJATP-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

pantoic acid (CHEBI:18697 )

Ontology

Not Available

Exogenous (HMDB: HMDB0240389)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.59	ALOGPS
logP	-0.49	ChemAxon
logS	0.32	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.01 m³·mol⁻¹	ChemAxon
Polarizability	14.36 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	131.653	30932474
DeepCCS	[M-H]-	127.824	30932474
DeepCCS	[M-2H]-	165.329	30932474
DeepCCS	[M+Na]+	140.868	30932474
AllCCS	[M+H]+	134.3	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	138.0	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	130.3	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	135.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pantoic acid	CC(C)(CO)[C@@H](O)C(O)=O	2485.4	Standard polar	33892256
Pantoic acid	CC(C)(CO)[C@@H](O)C(O)=O	1208.6	Standard non polar	33892256
Pantoic acid	CC(C)(CO)[C@@H](O)C(O)=O	1266.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pantoic acid,1TMS,isomer #1	CC(C)(CO[Si](C)(C)C)[C@@H](O)C(=O)O	1365.0	Semi standard non polar	33892256
Pantoic acid,1TMS,isomer #2	CC(C)(CO)[C@@H](O[Si](C)(C)C)C(=O)O	1341.8	Semi standard non polar	33892256
Pantoic acid,1TMS,isomer #3	CC(C)(CO)[C@@H](O)C(=O)O[Si](C)(C)C	1267.6	Semi standard non polar	33892256
Pantoic acid,2TMS,isomer #1	CC(C)(CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O	1405.3	Semi standard non polar	33892256
Pantoic acid,2TMS,isomer #2	CC(C)(CO[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C	1376.4	Semi standard non polar	33892256
Pantoic acid,2TMS,isomer #3	CC(C)(CO)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1338.8	Semi standard non polar	33892256
Pantoic acid,3TMS,isomer #1	CC(C)(CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1427.8	Semi standard non polar	33892256
Pantoic acid,1TBDMS,isomer #1	CC(C)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O	1599.7	Semi standard non polar	33892256
Pantoic acid,1TBDMS,isomer #2	CC(C)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1587.7	Semi standard non polar	33892256
Pantoic acid,1TBDMS,isomer #3	CC(C)(CO)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1490.9	Semi standard non polar	33892256
Pantoic acid,2TBDMS,isomer #1	CC(C)(CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O	1866.0	Semi standard non polar	33892256
Pantoic acid,2TBDMS,isomer #2	CC(C)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C	1824.5	Semi standard non polar	33892256
Pantoic acid,2TBDMS,isomer #3	CC(C)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1815.8	Semi standard non polar	33892256
Pantoic acid,3TBDMS,isomer #1	CC(C)(CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2080.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pantoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00e9-9300000000-1533cf69a587ccbc946b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pantoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 10V, Positive-QTOF	splash10-001i-1900000000-7d32d9fe2f4c45ee7840	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 20V, Positive-QTOF	splash10-0fk9-9500000000-27fa4de1f52b9b39c2c7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 40V, Positive-QTOF	splash10-0abc-9100000000-4b387706b53ffaba5f68	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 10V, Negative-QTOF	splash10-0f6t-2900000000-ea603b384234b8b971d2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 20V, Negative-QTOF	splash10-00di-9600000000-c12f5dc91e63440b6213	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 40V, Negative-QTOF	splash10-00di-9000000000-921e587537e7f7b8173d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 10V, Negative-QTOF	splash10-0002-1900000000-d6c062a26d684557b37c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 20V, Negative-QTOF	splash10-00ba-9500000000-a1678e241f40c3991ed8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 40V, Negative-QTOF	splash10-05i3-9000000000-ff04a60d16aa9928a044	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 10V, Positive-QTOF	splash10-001r-4900000000-8f94035a9aca264573f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 20V, Positive-QTOF	splash10-074i-9100000000-d5f8b375fb7c5c114d19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pantoic acid 40V, Positive-QTOF	splash10-052f-9000000000-eff6aae246d496dfde6f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00007622

Chemspider ID

388387

KEGG Compound ID

C00522

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pantoic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18697

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

STANSLY PG, SCHLOSSER ME: The biological activity of pantolactone and pantoic acid. J Biol Chem. 1945 Dec;161:513-5. [PubMed:21006934 ]

Showing metabocard for Pantoic acid (HMDB0240389)

MOL for HMDB0240389 (Pantoic acid)

3D MOL for HMDB0240389 (Pantoic acid)

3D SDF for HMDB0240389 (Pantoic acid)

3D-SDF for HMDB0240389 (Pantoic acid)

PDB for HMDB0240389 (Pantoic acid)

3D PDB for HMDB0240389 (Pantoic acid)

SMILES for HMDB0240389 (Pantoic acid)

INCHI for HMDB0240389 (Pantoic acid)

Structure for HMDB0240389 (Pantoic acid)

3D Structure for HMDB0240389 (Pantoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra