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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:31:40 UTC

Update Date

2021-09-26 22:55:39 UTC

HMDB ID

HMDB0246510

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Methylhistamine

Description

4-Methylhistamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 4-Methylhistamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Methylhistamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-methylhistamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Methylhistamine 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
5-Methylhistamine	ChEBI
4-Methylhistamine dihydrochloride	HMDB
4-Methylhistamine hydride	HMDB

Chemical Formula

C₆H₁₁N₃

Average Molecular Weight

125.175

Monoisotopic Molecular Weight

125.095297366

IUPAC Name

2-(5-methyl-1H-imidazol-4-yl)ethan-1-amine

Traditional Name

4-methylhistamine

CAS Registry Number

Not Available

SMILES

CC1=C(CCN)N=CN1

InChI Identifier

InChI=1S/C6H11N3/c1-5-6(2-3-7)9-4-8-5/h4H,2-3,7H2,1H3,(H,8,9)

InChI Key

UGYXPZQILZRKJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

2-arylethylamines

Alternative Parents

Substituents

2-arylethylamine
Aralkylamine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:74760 )
aralkylamino compound (CHEBI:74760 )
a small molecule (CPD-10830 )

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	-0.4	ALOGPS
logP	-0.5	ChemAxon
logS	-0.01	ALOGPS
pKa (Strongest Acidic)	14.74	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.81 m³·mol⁻¹	ChemAxon
Polarizability	14.05 Å³	ChemAxon
Number of Rings	1	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]+	126.751	30932474
DeepCCS	[M-H]-	123.627	30932474
DeepCCS	[M-2H]-	160.624	30932474
DeepCCS	[M+Na]+	135.472	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.2	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	126.4	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	131.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	7.7217 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	342.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	54.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.5 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	225.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	927.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	507.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	33.5 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	527.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	793.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	658.2 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	351.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylhistamine	CC1=C(CCN)N=CN1	2270.0	Standard polar	33892256
4-Methylhistamine	CC1=C(CCN)N=CN1	1531.3	Standard non polar	33892256
4-Methylhistamine	CC1=C(CCN)N=CN1	1412.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methylhistamine,1TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=C[NH]1	1536.3	Semi standard non polar	33892256
4-Methylhistamine,1TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=C[NH]1	1555.6	Standard non polar	33892256
4-Methylhistamine,1TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=C[NH]1	1960.7	Standard polar	33892256
4-Methylhistamine,1TMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C	1527.6	Semi standard non polar	33892256
4-Methylhistamine,1TMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C	1492.0	Standard non polar	33892256
4-Methylhistamine,1TMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C	2121.2	Standard polar	33892256
4-Methylhistamine,2TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=CN1[Si](C)(C)C	1657.7	Semi standard non polar	33892256
4-Methylhistamine,2TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=CN1[Si](C)(C)C	1672.6	Standard non polar	33892256
4-Methylhistamine,2TMS,isomer #1	CC1=C(CCN[Si](C)(C)C)N=CN1[Si](C)(C)C	1860.8	Standard polar	33892256
4-Methylhistamine,2TMS,isomer #2	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	1798.1	Semi standard non polar	33892256
4-Methylhistamine,2TMS,isomer #2	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	1754.0	Standard non polar	33892256
4-Methylhistamine,2TMS,isomer #2	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=C[NH]1	1928.3	Standard polar	33892256
4-Methylhistamine,3TMS,isomer #1	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	1920.8	Semi standard non polar	33892256
4-Methylhistamine,3TMS,isomer #1	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	1860.2	Standard non polar	33892256
4-Methylhistamine,3TMS,isomer #1	CC1=C(CCN([Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C	1850.4	Standard polar	33892256
4-Methylhistamine,1TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=C[NH]1	1801.9	Semi standard non polar	33892256
4-Methylhistamine,1TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=C[NH]1	1788.8	Standard non polar	33892256
4-Methylhistamine,1TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=C[NH]1	2071.2	Standard polar	33892256
4-Methylhistamine,1TBDMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C(C)(C)C	1774.5	Semi standard non polar	33892256
4-Methylhistamine,1TBDMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C(C)(C)C	1683.0	Standard non polar	33892256
4-Methylhistamine,1TBDMS,isomer #2	CC1=C(CCN)N=CN1[Si](C)(C)C(C)(C)C	2180.0	Standard polar	33892256
4-Methylhistamine,2TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2141.9	Semi standard non polar	33892256
4-Methylhistamine,2TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2073.2	Standard non polar	33892256
4-Methylhistamine,2TBDMS,isomer #1	CC1=C(CCN[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2044.6	Standard polar	33892256
4-Methylhistamine,2TBDMS,isomer #2	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2228.0	Semi standard non polar	33892256
4-Methylhistamine,2TBDMS,isomer #2	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2171.6	Standard non polar	33892256
4-Methylhistamine,2TBDMS,isomer #2	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]1	2092.5	Standard polar	33892256
4-Methylhistamine,3TBDMS,isomer #1	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2546.5	Semi standard non polar	33892256
4-Methylhistamine,3TBDMS,isomer #1	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2453.9	Standard non polar	33892256
4-Methylhistamine,3TBDMS,isomer #1	CC1=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C	2158.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0032-9200000000-bc9882056b1d71bcffa5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylhistamine 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-Methylhistamine 10V, Positive-QTOF	splash10-0a4i-1900000000-d7d5b56185b8e29b9ae4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylhistamine 20V, Positive-QTOF	splash10-0a4i-9600000000-f2203fdee1740d3dfdf5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylhistamine 40V, Positive-QTOF	splash10-053u-9000000000-c2f15f4413986661cc69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylhistamine 10V, Negative-QTOF	splash10-001i-9200000000-c93d45eb9945e770c096	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylhistamine 20V, Negative-QTOF	splash10-00xr-9400000000-9025f6ff1a1ed56a4d04	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylhistamine 40V, Negative-QTOF	splash10-00kf-9000000000-822ca0512145b152290d	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

34368

KEGG Compound ID

C17929

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Methylhistamine

METLIN ID

Not Available

PubChem Compound

37463

PDB ID

Not Available

ChEBI ID

74760

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 4-Methylhistamine (HMDB0246510)

MOL for HMDB0246510 (4-Methylhistamine)

3D MOL for HMDB0246510 (4-Methylhistamine)

3D SDF for HMDB0246510 (4-Methylhistamine)

3D-SDF for HMDB0246510 (4-Methylhistamine)

PDB for HMDB0246510 (4-Methylhistamine)

3D PDB for HMDB0246510 (4-Methylhistamine)

SMILES for HMDB0246510 (4-Methylhistamine)

INCHI for HMDB0246510 (4-Methylhistamine)

Structure for HMDB0246510 (4-Methylhistamine)

3D Structure for HMDB0246510 (4-Methylhistamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra