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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 07:23:28 UTC

Update Date

2023-02-21 17:16:51 UTC

HMDB ID

HMDB0003929

Secondary Accession Numbers

HMDB03929

Metabolite Identification

Common Name

5-Aminoimidazole

Description

Because of its ability to mimic a low energy status of the cell, the cell-permeable nucleoside 5-aminoimidazole-4-carboxamide (AICA) riboside was proposed as an antineoplastic agent switching off major energy-consuming processes associated with the malignant phenotype (lipid production, DNA synthesis, cell proliferation, cell migration, etc.). Key to the antineoplastic action of AICA riboside is its conversion to ZMP, an AMP mimetic that at high concentrations activates the AMP-activated protein kinase (AMPK). (PMID: 16985054 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aminoimidazole	Kegg
4-Aminoimidazole	Kegg
5-Aminoimidazole	ChEBI

Chemical Formula

C₃H₅N₃

Average Molecular Weight

83.0919

Monoisotopic Molecular Weight

83.048347175

IUPAC Name

1H-imidazol-5-amine

Traditional Name

5-aminoimidazole

CAS Registry Number

4919-03-3

SMILES

NC1=CN=CN1

InChI Identifier

InChI=1S/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)

InChI Key

QRZMXADUXZADTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Aminoimidazoles

Alternative Parents

Substituents

Aminoimidazole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminoimidazole (CHEBI:16607 )
a small molecule (AMINO-IMIDAZOLE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0003929)

Source

Endogenous

Endogenous (HMDB: HMDB0003929)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	319 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.88	ChemAxon
logS	0.58	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	22.97 m³·mol⁻¹	ChemAxon
Polarizability	7.97 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
DarkChem	[M+H]+	112.546	31661259
DarkChem	[M-H]-	107.531	31661259
DeepCCS	[M+H]+	116.231	30932474
DeepCCS	[M-H]-	114.302	30932474
DeepCCS	[M-2H]-	149.865	30932474
DeepCCS	[M+Na]+	124.379	30932474
AllCCS	[M+H]+	119.3	32859911
AllCCS	[M+H-H2O]+	114.2	32859911
AllCCS	[M+NH4]+	124.2	32859911
AllCCS	[M+Na]+	125.6	32859911
AllCCS	[M-H]-	114.9	32859911
AllCCS	[M+Na-2H]-	118.7	32859911
AllCCS	[M+HCOO]-	122.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Aminoimidazole	NC1=CN=CN1	2568.1	Standard polar	33892256
5-Aminoimidazole	NC1=CN=CN1	1145.3	Standard non polar	33892256
5-Aminoimidazole	NC1=CN=CN1	1228.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Aminoimidazole,1TMS,isomer #1	C[Si](C)(C)NC1=CN=C[NH]1	1321.4	Semi standard non polar	33892256
5-Aminoimidazole,1TMS,isomer #1	C[Si](C)(C)NC1=CN=C[NH]1	1222.3	Standard non polar	33892256
5-Aminoimidazole,1TMS,isomer #1	C[Si](C)(C)NC1=CN=C[NH]1	2094.1	Standard polar	33892256
5-Aminoimidazole,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1N	1305.8	Semi standard non polar	33892256
5-Aminoimidazole,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1N	1206.3	Standard non polar	33892256
5-Aminoimidazole,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1N	2028.8	Standard polar	33892256
5-Aminoimidazole,2TMS,isomer #1	C[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C	1258.1	Semi standard non polar	33892256
5-Aminoimidazole,2TMS,isomer #1	C[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C	1412.1	Standard non polar	33892256
5-Aminoimidazole,2TMS,isomer #1	C[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C	1832.9	Standard polar	33892256
5-Aminoimidazole,2TMS,isomer #2	C[Si](C)(C)NC1=CN=CN1[Si](C)(C)C	1419.7	Semi standard non polar	33892256
5-Aminoimidazole,2TMS,isomer #2	C[Si](C)(C)NC1=CN=CN1[Si](C)(C)C	1366.1	Standard non polar	33892256
5-Aminoimidazole,2TMS,isomer #2	C[Si](C)(C)NC1=CN=CN1[Si](C)(C)C	1947.4	Standard polar	33892256
5-Aminoimidazole,3TMS,isomer #1	C[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1487.1	Semi standard non polar	33892256
5-Aminoimidazole,3TMS,isomer #1	C[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1493.3	Standard non polar	33892256
5-Aminoimidazole,3TMS,isomer #1	C[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	1585.7	Standard polar	33892256
5-Aminoimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CN=C[NH]1	1518.5	Semi standard non polar	33892256
5-Aminoimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CN=C[NH]1	1430.7	Standard non polar	33892256
5-Aminoimidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CN=C[NH]1	2303.3	Standard polar	33892256
5-Aminoimidazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1N	1524.1	Semi standard non polar	33892256
5-Aminoimidazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1N	1384.1	Standard non polar	33892256
5-Aminoimidazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1N	2165.5	Standard polar	33892256
5-Aminoimidazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	1680.2	Semi standard non polar	33892256
5-Aminoimidazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	1808.9	Standard non polar	33892256
5-Aminoimidazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	1971.5	Standard polar	33892256
5-Aminoimidazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CN=CN1[Si](C)(C)C(C)(C)C	1878.1	Semi standard non polar	33892256
5-Aminoimidazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CN=CN1[Si](C)(C)C(C)(C)C	1794.9	Standard non polar	33892256
5-Aminoimidazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=CN=CN1[Si](C)(C)C(C)(C)C	2138.3	Standard polar	33892256
5-Aminoimidazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2129.6	Semi standard non polar	33892256
5-Aminoimidazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2095.2	Standard non polar	33892256
5-Aminoimidazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1903.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Aminoimidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-b7f12da8e2a5e1822034	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Aminoimidazole 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 - 5-Aminoimidazole 10V, Positive-QTOF	splash10-001i-9000000000-775bbd8098911ec4aa11	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 20V, Positive-QTOF	splash10-0a59-9000000000-075581ac53eac2cff1cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 40V, Positive-QTOF	splash10-054o-9000000000-63146729dde1e3b109e2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 10V, Negative-QTOF	splash10-001i-9000000000-ef930e78c28038c9badf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 20V, Negative-QTOF	splash10-053r-9000000000-0acc92e0f19da4e18a20	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 40V, Negative-QTOF	splash10-014i-9000000000-c8e07ecd5bf1e8146136	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 10V, Negative-QTOF	splash10-001i-9000000000-3c279b1eddb7eb96d639	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 20V, Negative-QTOF	splash10-001i-9000000000-f5a9901a1d655bdceefb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 40V, Negative-QTOF	splash10-014l-9000000000-2655b37ef52173453d6c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 10V, Positive-QTOF	splash10-001i-9000000000-cc88d9cd94ae7b2c176d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 20V, Positive-QTOF	splash10-0a5c-9000000000-72413771e65dbb225a23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Aminoimidazole 40V, Positive-QTOF	splash10-052f-9000000000-b8c30c58a1f18729c4c4	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)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

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

FDB023250

KNApSAcK ID

Not Available

Chemspider ID

470

KEGG Compound ID

C05239

BioCyc ID

CPD-54

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6989

PubChem Compound

484

PDB ID

Not Available

ChEBI ID

16607

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

Laikind PK, Seegmiller JE, Gruber HE: Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Anal Biochem. 1986 Jul;156(1):81-90. [PubMed:3740420 ]
Beckers A, Organe S, Timmermans L, Vanderhoydonc F, Deboel L, Derua R, Waelkens E, Brusselmans K, Verhoeven G, Swinnen JV: Methotrexate enhances the antianabolic and antiproliferative effects of 5-aminoimidazole-4-carboxamide riboside. Mol Cancer Ther. 2006 Sep;5(9):2211-7. [PubMed:16985054 ]

Showing metabocard for 5-Aminoimidazole (HMDB0003929)

MOL for HMDB0003929 (5-Aminoimidazole)

3D MOL for HMDB0003929 (5-Aminoimidazole)

3D SDF for HMDB0003929 (5-Aminoimidazole)

3D-SDF for HMDB0003929 (5-Aminoimidazole)

PDB for HMDB0003929 (5-Aminoimidazole)

3D PDB for HMDB0003929 (5-Aminoimidazole)

SMILES for HMDB0003929 (5-Aminoimidazole)

INCHI for HMDB0003929 (5-Aminoimidazole)

Structure for HMDB0003929 (5-Aminoimidazole)

3D Structure for HMDB0003929 (5-Aminoimidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra