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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:11:02 UTC

Update Date

2022-09-22 17:45:00 UTC

HMDB ID

HMDB0243497

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Gulono-1,4-lactone

Description

D-Gulono-1,4-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. Based on a literature review very few articles have been published on D-Gulono-1,4-lactone. This compound has been identified in human blood as reported by (PMID: 31557052 ). D-gulono-1,4-lactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically D-Gulono-1,4-lactone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
D-Galactonate, .gamma.-lactone	HMDB

Chemical Formula

C₆H₁₀O₆

Average Molecular Weight

178.14

Monoisotopic Molecular Weight

178.047738042

IUPAC Name

5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one

Traditional Name

gulono-1,4-lactone

CAS Registry Number

Not Available

SMILES

OCC(O)C1OC(=O)C(O)C1O

InChI Identifier

InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2

InChI Key

SXZYCXMUPBBULW-UHFFFAOYSA-N

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

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

gamma-lactone (CHEBI:5571 )
a small molecule (L-GULONO-1-4-LACTONE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	-2	ALOGPS
logP	-2.7	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.78 m³·mol⁻¹	ChemAxon
Polarizability	15.62 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	139.372	30932474
DeepCCS	[M-H]-	136.599	30932474
DeepCCS	[M-2H]-	173.291	30932474
DeepCCS	[M+Na]+	148.543	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	130.8	32859911
AllCCS	[M+Na-2H]-	131.8	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Gulono-1,4-lactone	OCC(O)C1OC(=O)C(O)C1O	3688.8	Standard polar	33892256
D-Gulono-1,4-lactone	OCC(O)C1OC(=O)C(O)C1O	1929.3	Standard non polar	33892256
D-Gulono-1,4-lactone	OCC(O)C1OC(=O)C(O)C1O	1731.9	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 - D-Gulono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-9500000000-59a9f3f06e48d61e2393	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Gulono-1,4-lactone GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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 - D-Gulono-1,4-lactone 10V, Positive-QTOF	splash10-01t9-1900000000-f19abad99bdf73b1efe5	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 20V, Positive-QTOF	splash10-03di-5900000000-1c33e03f527449eeffe3	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 40V, Positive-QTOF	splash10-0a4i-9100000000-d0f024aeab0e4c79148c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 10V, Negative-QTOF	splash10-00or-3900000000-5f8e27814cf4a835d41a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 20V, Negative-QTOF	splash10-0ar0-6900000000-9a9aef2bcc37f743beab	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 40V, Negative-QTOF	splash10-0596-9100000000-f6f46082ded01b797996	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 10V, Positive-QTOF	splash10-01tc-1900000000-357411ada46438e527f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 20V, Positive-QTOF	splash10-0296-9400000000-9a21baca9dd7690b9d8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 40V, Positive-QTOF	splash10-06y7-9000000000-5a3e7e7c9c04ee2d5e63	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 10V, Negative-QTOF	splash10-056r-2900000000-544fc16c423313a33dcd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 20V, Negative-QTOF	splash10-0a4l-9000000000-38a961d49372af8052fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Gulono-1,4-lactone 40V, Negative-QTOF	splash10-0006-9000000000-3b73ec212cbc4b8626f7	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

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

Not Available

Chemspider ID

588

KEGG Compound ID

C05410

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

608

PDB ID

Not Available

ChEBI ID

5571

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for D-Gulono-1,4-lactone (HMDB0243497)

MOL for HMDB0243497 (D-Gulono-1,4-lactone)

3D MOL for HMDB0243497 (D-Gulono-1,4-lactone)

3D SDF for HMDB0243497 (D-Gulono-1,4-lactone)

3D-SDF for HMDB0243497 (D-Gulono-1,4-lactone)

PDB for HMDB0243497 (D-Gulono-1,4-lactone)

3D PDB for HMDB0243497 (D-Gulono-1,4-lactone)

SMILES for HMDB0243497 (D-Gulono-1,4-lactone)

INCHI for HMDB0243497 (D-Gulono-1,4-lactone)

Structure for HMDB0243497 (D-Gulono-1,4-lactone)

3D Structure for HMDB0243497 (D-Gulono-1,4-lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra