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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:33:14 UTC

Update Date

2023-02-21 17:27:22 UTC

HMDB ID

HMDB0040002

Secondary Accession Numbers

HMDB40002

Metabolite Identification

Common Name

1-(2-Thienyl)-1,2-propanedione

Description

1-(2-Thienyl)-1,2-propanedione belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group. Based on a literature review very few articles have been published on 1-(2-Thienyl)-1,2-propanedione.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Thienyl)propane-1,2-dione	HMDB
2-Pyruvoylthiophene	HMDB

Chemical Formula

C₇H₆O₂S

Average Molecular Weight

154.186

Monoisotopic Molecular Weight

154.008850126

IUPAC Name

1-(thiophen-2-yl)propane-1,2-dione

Traditional Name

1-(thiophen-2-yl)propane-1,2-dione

CAS Registry Number

13678-69-8

SMILES

CC(=O)C(=O)C1=CC=CS1

InChI Identifier

InChI=1S/C7H6O2S/c1-5(8)7(9)6-3-2-4-10-6/h2-4H,1H3

InChI Key

FDYDDUUWFJQMQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl ketones

Alternative Parents

Substituents

Aryl ketone
Alpha-diketone
Heteroaromatic compound
Thiophene
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040002)
Cytoplasm (HMDB: HMDB0040002)

Source

Exogenous

Exogenous (HMDB: HMDB0040002)

Food

Food (HMDB: HMDB0040002)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040002)

Biological role

Nutrient (HMDB: HMDB0040002)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	237.00 to 238.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	11670 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.965 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.73	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.87	ChemAxon
pKa (Strongest Basic)	-8.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.7 m³·mol⁻¹	ChemAxon
Polarizability	14.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.97	31661259
DarkChem	[M-H]-	127.316	31661259
DeepCCS	[M+H]+	136.169	30932474
DeepCCS	[M-H]-	133.93	30932474
DeepCCS	[M-2H]-	169.587	30932474
DeepCCS	[M+Na]+	143.752	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	124.7	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	132.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.47 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1318 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1474.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	463.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	371.4 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	457.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	215.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	977.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	337.1 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	1059.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	488.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.7 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	85.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(2-Thienyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=CS1	2018.4	Standard polar	33892256
1-(2-Thienyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=CS1	1154.9	Standard non polar	33892256
1-(2-Thienyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=CS1	1242.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(2-Thienyl)-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CS1	1450.6	Semi standard non polar	33892256
1-(2-Thienyl)-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CS1	1448.0	Standard non polar	33892256
1-(2-Thienyl)-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CS1	1672.1	Semi standard non polar	33892256
1-(2-Thienyl)-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CS1	1672.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2-Thienyl)-1,2-propanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3900000000-3261ef1e2dc890b02b18	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 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 - 1-(2-Thienyl)-1,2-propanedione 10V, Positive-QTOF	splash10-0a4r-0900000000-2cd637e13cf04345126f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 20V, Positive-QTOF	splash10-052r-4900000000-b9ed096435d3516c4ee5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 40V, Positive-QTOF	splash10-000i-9300000000-4794474026fde8907cde	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 10V, Negative-QTOF	splash10-0udi-0900000000-912cbfa0b1b5b5b412fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 20V, Negative-QTOF	splash10-001i-9700000000-0052bde92f80364dfc9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 40V, Negative-QTOF	splash10-0a4i-9100000000-6537ccf6d0e41fef675f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 10V, Positive-QTOF	splash10-0a4i-0900000000-989de56749f0bfdedabf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 20V, Positive-QTOF	splash10-03dl-6900000000-61ab3a855dee97d82c1f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 40V, Positive-QTOF	splash10-03dl-9700000000-d646308d069fd4f32742	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 10V, Negative-QTOF	splash10-0f89-9700000000-4ee98701a7f3361f6f46	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 20V, Negative-QTOF	splash10-001i-9000000000-7d99ce9954aa98dbedf6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(2-Thienyl)-1,2-propanedione 40V, Negative-QTOF	splash10-053r-9000000000-bbf148bf79102ad395c1	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB019684

KNApSAcK ID

Not Available

Chemspider ID

75476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83652

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1586661

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1-(2-Thienyl)-1,2-propanedione (HMDB0040002)

MOL for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

3D MOL for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

3D SDF for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

3D-SDF for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

PDB for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

3D PDB for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

SMILES for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

INCHI for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

Structure for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

3D Structure for HMDB0040002 (1-(2-Thienyl)-1,2-propanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra