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

2021-09-11 00:31:03 UTC

Update Date

2021-09-26 22:57:15 UTC

HMDB ID

HMDB0247512

Secondary Accession Numbers

None

Metabolite Identification

Common Name

7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine

Description

7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine, also known as MBMTPP, 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 a significant number of articles have been published on 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 7-methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 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


  Mrv1652309112102312D          

 14 15  0  0  0  0            999 V2000
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247512

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=C(C)C(SC)=C2C=NC=CN12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2S2/c1-7-9(13-2)8-6-11-4-5-12(8)10(7)14-3/h4-6H,1-3H3

> <INCHI_KEY>
MYLBTCQBKAKUTJ-UHFFFAOYSA-N

> <FORMULA>
C10H12N2S2

> <MOLECULAR_WEIGHT>
224.34

> <EXACT_MASS>
224.044190742

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
24.196638839292042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.2512340440000003

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6423970551517408

> <JCHEM_POLAR_SURFACE_AREA>
17.3

> <JCHEM_REFRACTIVITY>
65.7961

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.590  -0.533   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.258  -2.073   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       1.650  -4.013   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       1.650   1.408   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    3   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0247512
HETATM    1  C1  UNL     1       4.127   0.118  -0.167  1.00  0.00           C  
HETATM    2  S1  UNL     1       2.899  -1.162  -0.224  1.00  0.00           S  
HETATM    3  C2  UNL     1       1.227  -0.595  -0.142  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.154  -1.454  -0.174  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.207  -2.936  -0.277  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.045  -0.722  -0.093  1.00  0.00           C  
HETATM    7  S2  UNL     1      -2.650  -1.496  -0.105  1.00  0.00           S  
HETATM    8  C6  UNL     1      -3.998  -0.351   0.009  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.675   0.566  -0.014  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.430   1.670   0.081  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.790   2.895   0.149  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.545   2.998   0.122  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.314   1.894   0.027  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.687   0.670  -0.041  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.135  -0.406  -0.213  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.133   0.617   0.821  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.153   0.811  -1.033  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.713  -3.323  -0.773  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.137  -3.268  -0.764  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.225  -3.401   0.749  1.00  0.00           H  
HETATM   21  H7  UNL     1      -4.130   0.328  -0.862  1.00  0.00           H  
HETATM   22  H8  UNL     1      -4.946  -0.986  -0.007  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.020   0.146   0.993  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.507   1.643   0.107  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.426   3.787   0.227  1.00  0.00           H  
HETATM   26  H12 UNL     1       2.384   1.958   0.004  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4   14   14
CONECT    4    5    6    6
CONECT    5   18   19   20
CONECT    6    7    9
CONECT    7    8
CONECT    8   21   22   23
CONECT    9   10   14
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13
CONECT   13   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
MBMTPP	HMDB
7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine	MeSH

Chemical Formula

C₁₀H₁₂N₂S₂

Average Molecular Weight

224.34

Monoisotopic Molecular Weight

224.044190742

IUPAC Name

7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine

Traditional Name

7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine

CAS Registry Number

Not Available

SMILES

CSC1=C(C)C(SC)=C2C=NC=CN12

InChI Identifier

InChI=1S/C10H12N2S2/c1-7-9(13-2)8-6-11-4-5-12(8)10(7)14-3/h4-6H,1-3H3

InChI Key

MYLBTCQBKAKUTJ-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
Aryl thioether
Alkylarylthioether
Pyrazine
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Azacycle
Thioether
Sulfenyl compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organosulfur compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.21	ALOGPS
logP	2.25	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-1.6	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	2	ChemAxon
Refractivity	65.8 m³·mol⁻¹	ChemAxon
Polarizability	24.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M-2H]-	180.407	30932474
DeepCCS	[M+Na]+	155.945	30932474
AllCCS	[M+H]+	145.3	32859911
AllCCS	[M+H-H2O]+	141.4	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.1	32859911
AllCCS	[M-H]-	148.7	32859911
AllCCS	[M+Na-2H]-	149.1	32859911
AllCCS	[M+HCOO]-	149.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.6691 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.72 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1484.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	408.5 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	507.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	999.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	156.2 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	1284.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	316.1 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	59.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine	CSC1=C(C)C(SC)=C2C=NC=CN12	2667.4	Standard polar	33892256
7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine	CSC1=C(C)C(SC)=C2C=NC=CN12	2006.7	Standard non polar	33892256
7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine	CSC1=C(C)C(SC)=C2C=NC=CN12	2018.8	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 - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-4950000000-b1201c502953062af1ac	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(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 - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 10V, Negative-QTOF	splash10-00di-0390000000-7ac55b84b3c00c500772	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 20V, Negative-QTOF	splash10-0002-9020000000-dd1612ff66c6506fd2ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 40V, Negative-QTOF	splash10-0002-7910000000-a74a2da6ffa279bafd4d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 10V, Positive-QTOF	splash10-004i-0090000000-a50fd49342d78e84671f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 20V, Positive-QTOF	splash10-004i-0390000000-db492d9d93194f3a5179	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine 40V, Positive-QTOF	splash10-02t9-2900000000-0b242c3003aca874b5fe	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

113963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128585

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 ]

Showing metabocard for 7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine (HMDB0247512)

MOL for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

3D MOL for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

3D SDF for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

3D-SDF for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

PDB for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

3D PDB for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

SMILES for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

INCHI for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

Structure for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

3D Structure for HMDB0247512 (7-Methyl-6,8-bis(methylthio)pyrrolo(1,2-a)pyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra