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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:54:10 UTC

Update Date

2023-02-21 17:23:12 UTC

HMDB ID

HMDB0033173

Secondary Accession Numbers

HMDB33173

Metabolite Identification

Common Name

4-Methylpyrrolo[1,2-a]pyrazine

Description

4-Methylpyrrolo[1,2-a]pyrazine belongs to the class of organic compounds known as pyrrolopyrazines. Pyrrolopyrazines are compounds containing a pyrrolopyrazine moiety, which consists of a pyrrole ring fused to a pyrazine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4. Based on a literature review very few articles have been published on 4-Methylpyrrolo[1,2-a]pyrazine.

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

C₈H₈N₂

Average Molecular Weight

132.1625

Monoisotopic Molecular Weight

132.068748266

IUPAC Name

4-methylpyrrolo[1,2-a]pyrazine

Traditional Name

4-methylpyrrolo[1,2-a]pyrazine

CAS Registry Number

64608-60-2

SMILES

CC1=CN=CC2=CC=CN12

InChI Identifier

InChI=1S/C8H8N2/c1-7-5-9-6-8-3-2-4-10(7)8/h2-6H,1H3

InChI Key

GCXGRZISVBCADH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolopyrazines. Pyrrolopyrazines are compounds containing a pyrrolopyrazine moiety, which consists of a pyrrole ring fused to a pyrazine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrazines

Sub Class

Not Available

Direct Parent

Pyrrolopyrazines

Alternative Parents

Substituents

Pyrrolopyrazine
Pyrazine
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033173)
Cytoplasm (HMDB: HMDB0033173)

Source

Exogenous

Exogenous (HMDB: HMDB0033173)

Food

Food (HMDB: HMDB0033173)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033173)

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	1445 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	20.2 g/L	ALOGPS
logP	1.26	ALOGPS
logP	0.59	ChemAxon
logS	-0.82	ALOGPS
pKa (Strongest Basic)	-0.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.13 m³·mol⁻¹	ChemAxon
Polarizability	14.14 Å³	ChemAxon
Number of Rings	2	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]+	125.744	31661259
DarkChem	[M-H]-	122.686	31661259
DeepCCS	[M-2H]-	160.686	30932474
DeepCCS	[M+Na]+	135.739	30932474
AllCCS	[M+H]+	124.3	32859911
AllCCS	[M+H-H2O]+	119.4	32859911
AllCCS	[M+NH4]+	129.0	32859911
AllCCS	[M+Na]+	130.3	32859911
AllCCS	[M-H]-	124.6	32859911
AllCCS	[M+Na-2H]-	125.9	32859911
AllCCS	[M+HCOO]-	127.3	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.	2.87 minutes	32390414
Predicted by Siyang on May 30, 2022	8.3557 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	201.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	372.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.6 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	222.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	647.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	554.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	37.0 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	560.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	594.1 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	206.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylpyrrolo[1,2-a]pyrazine	CC1=CN=CC2=CC=CN12	2063.5	Standard polar	33892256
4-Methylpyrrolo[1,2-a]pyrazine	CC1=CN=CC2=CC=CN12	1306.7	Standard non polar	33892256
4-Methylpyrrolo[1,2-a]pyrazine	CC1=CN=CC2=CC=CN12	1307.3	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 - 4-Methylpyrrolo[1,2-a]pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3900000000-b1ed06e5a1e928ad6530	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 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 - 4-Methylpyrrolo[1,2-a]pyrazine 10V, Positive-QTOF	splash10-001i-0900000000-bae00382ff563e6da946	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 20V, Positive-QTOF	splash10-001i-0900000000-7097a7864c734f5806e7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 40V, Positive-QTOF	splash10-0fsl-9300000000-72efaeb7e6c584c2719a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 10V, Negative-QTOF	splash10-001i-0900000000-66a088e2fa6c7338bdf3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 20V, Negative-QTOF	splash10-001i-0900000000-fecf71392ef73817b531	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 40V, Negative-QTOF	splash10-001i-4900000000-977e06e1093ac647380b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 10V, Negative-QTOF	splash10-001i-0900000000-546ff4527c4c3d89ff23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 20V, Negative-QTOF	splash10-001i-0900000000-0e5a4c7303ac85910a92	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 40V, Negative-QTOF	splash10-01ox-9300000000-c27fe00219a56b210672	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 10V, Positive-QTOF	splash10-001i-0900000000-ccaafacb3cf306c2544d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 20V, Positive-QTOF	splash10-053r-7900000000-d0f5b2bb375e192317eb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylpyrrolo[1,2-a]pyrazine 40V, Positive-QTOF	splash10-0fal-9100000000-10ffeee030328f24ddf9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB011182

KNApSAcK ID

Not Available

Chemspider ID

507119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

583433

PDB ID

Not Available

ChEBI ID

173356

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1630521

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 4-Methylpyrrolo[1,2-a]pyrazine (HMDB0033173)

MOL for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

3D MOL for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

3D SDF for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

3D-SDF for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

PDB for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

3D PDB for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

SMILES for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

INCHI for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

Structure for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

3D Structure for HMDB0033173 (4-Methylpyrrolo[1,2-a]pyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra