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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:54:18 UTC

Update Date

2021-10-01 18:49:51 UTC

HMDB ID

HMDB0245856

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Deoxyglucosone

Description

3-Deoxyglucosone belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Based on a literature review a significant number of articles have been published on 3-Deoxyglucosone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-deoxyglucosone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Deoxyglucosone 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₁₀O₅

Average Molecular Weight

162.141

Monoisotopic Molecular Weight

162.052823422

IUPAC Name

4,5,6-trihydroxy-2-oxohexanal

Traditional Name

3-deoxyglucosone

CAS Registry Number

Not Available

SMILES

OCC(O)C(O)CC(=O)C=O

InChI Identifier

InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2

InChI Key

ZGCHLOWZNKRZSN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Medium-chain aldehyde
Beta-hydroxy ketone
Alpha-ketoaldehyde
1,2-diol
Ketone
Secondary alcohol
Polyol
Aldehyde
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

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	-1.6	ALOGPS
logP	-1.6	ChemAxon
logS	0.26	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.38 m³·mol⁻¹	ChemAxon
Polarizability	14.63 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]+	133.938	30932474
DeepCCS	[M-H]-	130.231	30932474
DeepCCS	[M-2H]-	167.81	30932474
DeepCCS	[M+Na]+	143.059	30932474
AllCCS	[M+H]+	137.3	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	141.0	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	131.0	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Deoxyglucosone	OCC(O)C(O)CC(=O)C=O	2947.9	Standard polar	33892256
3-Deoxyglucosone	OCC(O)C(O)CC(=O)C=O	1416.5	Standard non polar	33892256
3-Deoxyglucosone	OCC(O)C(O)CC(=O)C=O	1542.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Deoxyglucosone,4TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(C=C(C=O)O[Si](C)(C)C)O[Si](C)(C)C	1868.2	Semi standard non polar	33892256
3-Deoxyglucosone,4TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(C=C(C=O)O[Si](C)(C)C)O[Si](C)(C)C	1766.7	Standard non polar	33892256
3-Deoxyglucosone,4TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(C=C(C=O)O[Si](C)(C)C)O[Si](C)(C)C	1716.5	Standard polar	33892256
3-Deoxyglucosone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C=C(C=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2765.7	Semi standard non polar	33892256
3-Deoxyglucosone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C=C(C=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2477.6	Standard non polar	33892256
3-Deoxyglucosone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(C=C(C=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2193.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0nmi-9400000000-9d62ca57cbbe910b72e0	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Deoxyglucosone GC-MS (TBDMS_2_5) - 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 - 3-Deoxyglucosone 10V, Positive-QTOF	splash10-004i-4900000000-31f51d6502205058d105	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Deoxyglucosone 20V, Positive-QTOF	splash10-00g0-9400000000-3f30de686f245cbbe28d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Deoxyglucosone 40V, Positive-QTOF	splash10-052f-9000000000-20f6d2049d9f87b60692	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Deoxyglucosone 10V, Negative-QTOF	splash10-029x-2900000000-878cfb225e7b8a57ad65	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Deoxyglucosone 20V, Negative-QTOF	splash10-05fu-9100000000-d8c27511c192cd6b304f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Deoxyglucosone 40V, Negative-QTOF	splash10-0006-9000000000-f9d8541250d8b6b5c575	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

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

10784988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Deoxyglucosone

METLIN ID

Not Available

PubChem Compound

15120156

PDB ID

Not Available

ChEBI ID

Not Available

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 ]

Enzymes

Enzyme Details

1. Alcohol dehydrogenase [NADP(+)]

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
Gene Name:: AKR1A1
Uniprot ID:: P14550
Molecular weight:: 36572.71

Enzyme Details

2. Aldo-keto reductase family 1 member A1

General function:: Not Available
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosaccharides and bile acids, with a preference for negatively charged substrates, such as glucuronate and succinic semialdehyde (By similarity). Plays an important role in ascorbic acid biosynthesis by catalyzing the reduction of D-glucuronic acid and D-glucurono-gamma-lactone (By similarity). Functions as a detoxifiying enzyme by reducing a range of toxic aldehydes. Reduces methylglyoxal and 3-deoxyglucosone, which are present at elevated levels under hyperglycemic conditions and are cytotoxic. Involved also in the detoxification of lipid-derived aldehydes like acrolein (By similarity). Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs (By similarity). Displays no reductase activity towards retinoids (PubMed:12732097).
Gene Name:: AKR1A1
Uniprot ID:: P50578
Molecular weight:: 36581.71

Showing metabocard for 3-Deoxyglucosone (HMDB0245856)

MOL for HMDB0245856 (3-Deoxyglucosone)

3D MOL for HMDB0245856 (3-Deoxyglucosone)

3D SDF for HMDB0245856 (3-Deoxyglucosone)

3D-SDF for HMDB0245856 (3-Deoxyglucosone)

PDB for HMDB0245856 (3-Deoxyglucosone)

3D PDB for HMDB0245856 (3-Deoxyglucosone)

SMILES for HMDB0245856 (3-Deoxyglucosone)

INCHI for HMDB0245856 (3-Deoxyglucosone)

Structure for HMDB0245856 (3-Deoxyglucosone)

3D Structure for HMDB0245856 (3-Deoxyglucosone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes