Jump To Section:

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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:27:26 UTC

Update Date

2021-09-26 22:53:49 UTC

HMDB ID

HMDB0245382

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3-Butanedione monoxime

Description

2,3-Butanedione monoxime, also known as diacetyl monooxime or DAM, belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl). Based on a literature review a significant number of articles have been published on 2,3-Butanedione monoxime. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,3-butanedione monoxime is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,3-Butanedione monoxime 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

Value	Source
2,3-Butadione monooxime	ChEBI
2,3-Butanedione 3-monoxime	ChEBI
2,3-Butanedione oxime	ChEBI
2,3-Butanedione-2-monoxime	ChEBI
2-Hydroxyimino-3-butanone	ChEBI
2-Oximino-3-butanone	ChEBI
3-(Hydroxyimino)-2-butanone	ChEBI
3-Oximino-2-butanone	ChEBI
3-oxo-2-Butanone oxime	ChEBI
Biacetyl monooxime	ChEBI
Biacetyl monoxime	ChEBI
DAM	ChEBI
DAM (oxime)	ChEBI
Diacetyl monooxime	ChEBI
Diacetyl monoxime	ChEBI
Isonitrosoethyl methyl ketone	ChEBI
2,3-BDMO	HMDB
2,3-Butanedione monooxime	HMDB
KBDO	HMDB
Butanedione monoxime	HMDB
Diacetylmonoxime	HMDB
Potassium 2,3-butanedione monoximate	HMDB

Chemical Formula

C₄H₇NO₂

Average Molecular Weight

101.105

Monoisotopic Molecular Weight

101.047678469

IUPAC Name

3-(hydroxyimino)butan-2-one

Traditional Name

2,3-butanedione monoxime

CAS Registry Number

Not Available

SMILES

CC(=O)C(C)=NO

InChI Identifier

InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3

InChI Key

FSEUPUDHEBLWJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl).

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Oximes

Direct Parent

Ketoximes

Alternative Parents

Substituents

Ketoxime
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	0.11	ALOGPS
logP	0.4	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	6.5	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.36 m³·mol⁻¹	ChemAxon
Polarizability	9.82 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]+	121.017	30932474
DeepCCS	[M-H]-	118.587	30932474
DeepCCS	[M-2H]-	154.895	30932474
DeepCCS	[M+Na]+	129.485	30932474
AllCCS	[M+H]+	125.9	32859911
AllCCS	[M+H-H2O]+	121.6	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.1	32859911
AllCCS	[M-H]-	123.6	32859911
AllCCS	[M+Na-2H]-	127.5	32859911
AllCCS	[M+HCOO]-	131.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.4241 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1090.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	364.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	109.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	308.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	312.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	158.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	213.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	850.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	476.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	368.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	153.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Butanedione monoxime	CC(=O)C(C)=NO	1287.7	Standard polar	33892256
2,3-Butanedione monoxime	CC(=O)C(C)=NO	982.7	Standard non polar	33892256
2,3-Butanedione monoxime	CC(=O)C(C)=NO	894.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Butanedione monoxime,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)=NO	1104.4	Semi standard non polar	33892256
2,3-Butanedione monoxime,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)=NO	1022.2	Standard non polar	33892256
2,3-Butanedione monoxime,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(C)=NO	1769.1	Standard polar	33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO	1304.3	Semi standard non polar	33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO	1216.8	Standard non polar	33892256
2,3-Butanedione monoxime,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(C)=NO	1890.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Butanedione monoxime GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-0ae61c80523b369f0012	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Butanedione monoxime 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 - 2,3-Butanedione monoxime 10V, Positive-QTOF	splash10-0006-9100000000-e8f7cf12225b5a16644a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 20V, Positive-QTOF	splash10-0006-9000000000-db15a804dc61430ea8f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 40V, Positive-QTOF	splash10-0006-9000000000-39a1996b6efbc076acb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 10V, Negative-QTOF	splash10-0udi-6900000000-321d395340f72b182650	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 20V, Negative-QTOF	splash10-014i-9200000000-12ffacc3ef4c64a9f736	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Butanedione monoxime 40V, Negative-QTOF	splash10-0006-9000000000-f796ba68f1900cd9a85d	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

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

4911363

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diacetyl_monoxime

METLIN ID

Not Available

PubChem Compound

6398969

PDB ID

Not Available

ChEBI ID

4480

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1595041

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 2,3-Butanedione monoxime (HMDB0245382)

MOL for HMDB0245382 (2,3-Butanedione monoxime)

3D MOL for HMDB0245382 (2,3-Butanedione monoxime)

3D SDF for HMDB0245382 (2,3-Butanedione monoxime)

3D-SDF for HMDB0245382 (2,3-Butanedione monoxime)

PDB for HMDB0245382 (2,3-Butanedione monoxime)

3D PDB for HMDB0245382 (2,3-Butanedione monoxime)

SMILES for HMDB0245382 (2,3-Butanedione monoxime)

INCHI for HMDB0245382 (2,3-Butanedione monoxime)

Structure for HMDB0245382 (2,3-Butanedione monoxime)

3D Structure for HMDB0245382 (2,3-Butanedione monoxime)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra