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

2021-09-10 22:51:21 UTC

Update Date

2021-09-26 22:54:30 UTC

HMDB ID

HMDB0245804

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Amitrole

Description

Amitrole, also known as aminotriazole or 3-AT, belongs to the class of organic compounds known as triazoles. Triazoles are compounds containing a five-member aromatic ring of two carbon atoms and three nitrogen atoms. Amitrole exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Amitrole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Amitrole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Amitrole 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
1H-1,2,4-Triazol-3-ylamine	ChEBI
2-Amino-1,3,4-triazole	ChEBI
3-Amino-1,2,4-triazole	ChEBI
3-Amino-S-triazole	ChEBI
3-AT	ChEBI
Aminotriazole	ChEBI
Amitrole	MeSH

Chemical Formula

C₂H₄N₄

Average Molecular Weight

84.08

Monoisotopic Molecular Weight

84.043596148

IUPAC Name

2,3-dihydro-1H-1,2,4-triazol-3-imine

Traditional Name

3-amino-1,2,4-triazole

CAS Registry Number

Not Available

SMILES

N=C1NNC=N1

InChI Identifier

InChI=1S/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)

InChI Key

KLSJWNVTNUYHDU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triazoles. Triazoles are compounds containing a five-member aromatic ring of two carbon atoms and three nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Triazoles

Alternative Parents

Substituents

Heteroaromatic compound
1,2,4-triazole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic amine (CHEBI:40036 )
triazoles (CHEBI:40036 )
Pesticides (C11261 )
a small molecule (CPD0-1491 )

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	-2.1	ALOGPS
logP	-1.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	6.15	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.27 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.38 m³·mol⁻¹	ChemAxon
Polarizability	7.34 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]+	119.289	30932474
DeepCCS	[M-H]-	117.394	30932474
DeepCCS	[M-2H]-	152.905	30932474
DeepCCS	[M+Na]+	127.386	30932474
AllCCS	[M+H]+	122.1	32859911
AllCCS	[M+H-H2O]+	117.1	32859911
AllCCS	[M+NH4]+	126.8	32859911
AllCCS	[M+Na]+	128.2	32859911
AllCCS	[M-H]-	114.6	32859911
AllCCS	[M+Na-2H]-	118.6	32859911
AllCCS	[M+HCOO]-	122.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amitrole	N=C1NNC=N1	2719.5	Standard polar	33892256
Amitrole	N=C1NNC=N1	1229.2	Standard non polar	33892256
Amitrole	N=C1NNC=N1	1575.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amitrole,1TMS,isomer #1	C[Si](C)(C)N=C1N=C[NH][NH]1	1229.5	Semi standard non polar	33892256
Amitrole,1TMS,isomer #1	C[Si](C)(C)N=C1N=C[NH][NH]1	1450.1	Standard non polar	33892256
Amitrole,1TMS,isomer #1	C[Si](C)(C)N=C1N=C[NH][NH]1	2180.6	Standard polar	33892256
Amitrole,1TMS,isomer #2	C[Si](C)(C)N1[NH]C=NC1=N	1261.3	Semi standard non polar	33892256
Amitrole,1TMS,isomer #2	C[Si](C)(C)N1[NH]C=NC1=N	1283.0	Standard non polar	33892256
Amitrole,1TMS,isomer #2	C[Si](C)(C)N1[NH]C=NC1=N	2317.1	Standard polar	33892256
Amitrole,1TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)[NH]1	1328.0	Semi standard non polar	33892256
Amitrole,1TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)[NH]1	1329.8	Standard non polar	33892256
Amitrole,1TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)[NH]1	2165.8	Standard polar	33892256
Amitrole,2TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)[NH]1	1347.3	Semi standard non polar	33892256
Amitrole,2TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)[NH]1	1456.5	Standard non polar	33892256
Amitrole,2TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)[NH]1	2052.2	Standard polar	33892256
Amitrole,2TMS,isomer #2	C[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C	1307.2	Semi standard non polar	33892256
Amitrole,2TMS,isomer #2	C[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C	1411.3	Standard non polar	33892256
Amitrole,2TMS,isomer #2	C[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C	2082.6	Standard polar	33892256
Amitrole,2TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C	1372.6	Semi standard non polar	33892256
Amitrole,2TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C	1376.3	Standard non polar	33892256
Amitrole,2TMS,isomer #3	C[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C	2154.0	Standard polar	33892256
Amitrole,3TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)N1[Si](C)(C)C	1466.3	Semi standard non polar	33892256
Amitrole,3TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)N1[Si](C)(C)C	1514.9	Standard non polar	33892256
Amitrole,3TMS,isomer #1	C[Si](C)(C)N=C1N=CN([Si](C)(C)C)N1[Si](C)(C)C	1938.0	Standard polar	33892256
Amitrole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C[NH][NH]1	1493.7	Semi standard non polar	33892256
Amitrole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C[NH][NH]1	1690.7	Standard non polar	33892256
Amitrole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C[NH][NH]1	2411.4	Standard polar	33892256
Amitrole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1[NH]C=NC1=N	1540.6	Semi standard non polar	33892256
Amitrole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1[NH]C=NC1=N	1449.5	Standard non polar	33892256
Amitrole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1[NH]C=NC1=N	2396.1	Standard polar	33892256
Amitrole,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)[NH]1	1599.5	Semi standard non polar	33892256
Amitrole,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)[NH]1	1536.9	Standard non polar	33892256
Amitrole,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)[NH]1	2324.8	Standard polar	33892256
Amitrole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)[NH]1	1800.0	Semi standard non polar	33892256
Amitrole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)[NH]1	1833.8	Standard non polar	33892256
Amitrole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)[NH]1	2213.5	Standard polar	33892256
Amitrole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C(C)(C)C	1765.1	Semi standard non polar	33892256
Amitrole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C(C)(C)C	1803.6	Standard non polar	33892256
Amitrole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C[NH]N1[Si](C)(C)C(C)(C)C	2201.9	Standard polar	33892256
Amitrole,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C(C)(C)C	1816.6	Semi standard non polar	33892256
Amitrole,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C(C)(C)C	1787.9	Standard non polar	33892256
Amitrole,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC(=N)N1[Si](C)(C)C(C)(C)C	2251.5	Standard polar	33892256
Amitrole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2073.5	Semi standard non polar	33892256
Amitrole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2126.6	Standard non polar	33892256
Amitrole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=CN([Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2131.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Amitrole GC-MS (2 TMS)	splash10-03di-6890000000-754b3b51d99b00d9a12a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Amitrole GC-MS (3 TMS)	splash10-000i-3940000000-d9c82cecc0ca53dbd9b7	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amitrole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-26d30fbdb47f1d8b39a2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amitrole 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amitrole 35V, Positive-QTOF	splash10-000i-9000000000-e37b362ad4d2717e1b89	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 10V, Positive-QTOF	splash10-000i-9000000000-c99f58af7e45f848dbda	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 20V, Positive-QTOF	splash10-000i-9000000000-f365faf2b853da634152	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 40V, Positive-QTOF	splash10-0a4i-9000000000-af199e373854b1891b2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 10V, Negative-QTOF	splash10-001i-9000000000-99a9f3545fabfc75dbad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 20V, Negative-QTOF	splash10-001i-9000000000-f5d4b0203fe8de3b4a09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 40V, Negative-QTOF	splash10-0006-9000000000-817d8db3192407931ec9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 10V, Positive-QTOF	splash10-000i-9000000000-4e6256bb02920a209ae7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 20V, Positive-QTOF	splash10-0006-9000000000-2033f0c22a7ff8bc8189	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 40V, Positive-QTOF	splash10-0a4i-9000000000-4ea03026f2d837e93cb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 10V, Negative-QTOF	splash10-001i-9000000000-f5b88d9f005edfd91c77	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 20V, Negative-QTOF	splash10-000x-9000000000-74364c2de00866321ea5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amitrole 40V, Negative-QTOF	splash10-014l-9000000000-1c8a5fd483f4741232f9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
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, 1000 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, 200 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	¹³C NMR Spectrum (1D, 300 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, 400 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, 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	¹H NMR Spectrum (1D, 600 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	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	¹H NMR Spectrum (1D, 800 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	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

1577

KEGG Compound ID

C11261

BioCyc ID

CPD0-1491

BiGG ID

Not Available

Wikipedia Link

Amitrole

METLIN ID

Not Available

PubChem Compound

1639

PDB ID

Not Available

ChEBI ID

40036

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1186891

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 Amitrole (HMDB0245804)

MOL for HMDB0245804 (Amitrole)

3D MOL for HMDB0245804 (Amitrole)

3D SDF for HMDB0245804 (Amitrole)

3D-SDF for HMDB0245804 (Amitrole)

PDB for HMDB0245804 (Amitrole)

3D PDB for HMDB0245804 (Amitrole)

SMILES for HMDB0245804 (Amitrole)

INCHI for HMDB0245804 (Amitrole)

Structure for HMDB0245804 (Amitrole)

3D Structure for HMDB0245804 (Amitrole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra