NP-MRD: Showing NP-Card for (R)-(-)-Pantolactone (NP0002719)

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Record Information

Version

1.0

Created at

2020-11-23 19:38:43 UTC

Updated at

2021-08-19 23:59:17 UTC

NP-MRD ID

NP0002719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-(-)-Pantolactone

Provided By

BMRB

Description

Dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone, also known as (R)-pantoyl lactone or 2,4-dihydroxy-3,3-dimethylbutyric acid gamma-lactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1981 (PMID: 7020480). Based on a literature review very few articles have been published on dihydro-3-hydroxy-4,4-dimethyl- 2(3H)-Furanone (PMID: 17984079) (PMID: 15195978).

Structure

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

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3R)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone	ChEBI
(R)-Pantoyl lactone	ChEBI
Pantolactone, 2-(14)C-labeled CPD, (+,-)-isomer	HMDB
Pantolactone, (R)-isomer	HMDB
Pantolactone, (S)-isomer	HMDB
Pantolactone	HMDB
2,4-Dihydroxy-3,3-dimethylbutyric acid gamma-lactone	HMDB
Pantoyl lactone	HMDB

Chemical Formula

C₆H₁₀O₃

Average Mass

130.1418 Da

Monoisotopic Mass

130.06299 Da

IUPAC Name

(3R)-3-hydroxy-4,4-dimethyloxolan-2-one

Traditional Name

pantolactone

CAS Registry Number

Not Available

SMILES

CC1(C)COC(=O)[C@@H]1O

InChI Identifier

InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1

InChI Key

SERHXTVXHNVDKA-BYPYZUCNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	92.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	224.61 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.800 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.27	ALOGPS
logP	0.18	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.52 m³·mol⁻¹	ChemAxon
Polarizability	12.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303902

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029751

KNApSAcK ID

Not Available

Chemspider ID

388488

KEGG Compound ID

C01012

BioCyc ID

PANTOYL-LACTONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439368

PDB ID

Not Available

ChEBI ID

16719

Good Scents ID

rw1140771

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Peinado RA, Moreno J, Medina M, Mauricio JC: Changes in volatile compounds and aromatic series in sherry wine with high gluconic acid levels subjected to aging by submerged flor yeast cultures. Biotechnol Lett. 2004 May;26(9):757-62. doi: 10.1023/b:bile.0000024102.58987.de. [PubMed:15195978 ]
Wilken DR, Dyar RE: Analysis of stereochemistry of enzymically formed pantoyl lactone or pantoic acid by gas chromatography and circular dichroism. Anal Biochem. 1981 Mar 15;112(1):9-16. doi: 10.1016/0003-2697(81)90253-0. [PubMed:7020480 ]

Showing NP-Card for (R)-(-)-Pantolactone (NP0002719)

MOL for NP0002719 ((R)-(-)-Pantolactone)

3D MOL for NP0002719 ((R)-(-)-Pantolactone)

3D SDF for NP0002719 ((R)-(-)-Pantolactone)

3D-SDF for NP0002719 ((R)-(-)-Pantolactone)

PDB for NP0002719 ((R)-(-)-Pantolactone)

3D PDB for NP0002719 ((R)-(-)-Pantolactone)

SMILES for NP0002719 ((R)-(-)-Pantolactone)

INCHI for NP0002719 ((R)-(-)-Pantolactone)

Structure for NP0002719 ((R)-(-)-Pantolactone)

3D Structure for NP0002719 ((R)-(-)-Pantolactone)