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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:32:56 UTC

Update Date

2023-02-21 17:27:21 UTC

HMDB ID

HMDB0039996

Secondary Accession Numbers

HMDB39996

Metabolite Identification

Common Name

2,3-Dimethyl-5-propylpyrazine

Description

2,3-Dimethyl-5-propylpyrazine belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2,3-Dimethyl-5-propylpyrazine has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and crustaceans. This could make 2,3-dimethyl-5-propylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,3-Dimethyl-5-propylpyrazine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Amylpyrazine	HMDB
N-Pentylpyrazine	HMDB
Pentylpyrazine	HMDB

Chemical Formula

C₉H₁₄N₂

Average Molecular Weight

150.2209

Monoisotopic Molecular Weight

150.115698458

IUPAC Name

2,3-dimethyl-5-propylpyrazine

Traditional Name

2,3-dimethyl-5-propylpyrazine

CAS Registry Number

32262-98-9

SMILES

CCCC1=NC(C)=C(C)N=C1

InChI Identifier

InChI=1S/C9H14N2/c1-4-5-9-6-10-7(2)8(3)11-9/h6H,4-5H2,1-3H3

InChI Key

RHCYSZMTNWMCOO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039996)
Cytoplasm (HMDB: HMDB0039996)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039996)

Source

Exogenous

Exogenous (HMDB: HMDB0039996)

Food

Food (HMDB: HMDB0039996)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Plant

Poaceae (HMDB: HMDB0039996)

Animal

Animal (HMDB: HMDB0039996)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039996)

Biological role

Nutrient (HMDB: HMDB0039996)

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	488.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.44 g/L	ALOGPS
logP	2.06	ALOGPS
logP	1.08	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.75 m³·mol⁻¹	ChemAxon
Polarizability	18.02 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]+	132.88	31661259
DarkChem	[M-H]-	131.689	31661259
DeepCCS	[M+H]+	140.22	30932474
DeepCCS	[M-H]-	136.392	30932474
DeepCCS	[M-2H]-	173.962	30932474
DeepCCS	[M+Na]+	149.5	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.7	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	136.6	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	140.0	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.	2.91 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2898 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	97.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	567.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	295.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.8 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	291.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	563.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	718.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	60.9 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	1201.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	450.4 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	205.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dimethyl-5-propylpyrazine	CCCC1=NC(C)=C(C)N=C1	1517.9	Standard polar	33892256
2,3-Dimethyl-5-propylpyrazine	CCCC1=NC(C)=C(C)N=C1	1119.4	Standard non polar	33892256
2,3-Dimethyl-5-propylpyrazine	CCCC1=NC(C)=C(C)N=C1	1168.3	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 - 2,3-Dimethyl-5-propylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-6900000000-d81db0072fbcdba38ed8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 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-Dimethyl-5-propylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-efe3af1ba8260583872e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 20V, Positive-QTOF	splash10-0udi-0900000000-78992132d5d8feb11de8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 40V, Positive-QTOF	splash10-0ldl-9100000000-17025bf0e69ecf497333	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-3e9cca56ccd449ab3028	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 20V, Negative-QTOF	splash10-0002-0900000000-afd8ef53c044903c0057	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 40V, Negative-QTOF	splash10-0apl-8900000000-c3c14baaeba5c1f0cb05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 10V, Negative-QTOF	splash10-0002-0900000000-50a674f3d9a955d9216b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 20V, Negative-QTOF	splash10-0002-1900000000-0ea87fe69a829564610a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 40V, Negative-QTOF	splash10-02td-9400000000-2ece37a2870b35085fce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 10V, Positive-QTOF	splash10-0udi-0900000000-3ac36e507add6e914f26	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 20V, Positive-QTOF	splash10-0kmi-2900000000-1836ad2fbe50c010eafd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dimethyl-5-propylpyrazine 40V, Positive-QTOF	splash10-0532-9400000000-bcceea973f8f0a07a532	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB019678

KNApSAcK ID

Not Available

Chemspider ID

454081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520566

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1881371

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 2,3-Dimethyl-5-propylpyrazine (HMDB0039996)

MOL for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

3D MOL for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

3D SDF for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

3D-SDF for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

PDB for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

3D PDB for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

SMILES for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

INCHI for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

Structure for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

3D Structure for HMDB0039996 (2,3-Dimethyl-5-propylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra