MiMeDB: Showing metabocard for 4-guanidinobutanal (MMDBc0054269)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:02:44 UTC

Update Date

2025-10-07 16:08:27 UTC

Metabolite ID

MMDBc0054269

Metabolite Identification

Common Name

4-guanidinobutanal

Description

4-guanidinobutanal is a guanidine derivative and belongs to the class of amino acids and their derivatives. Its chemical structure features a butanal backbone with a guanidine group, which contributes to its unique reactivity and potential biological roles. This metabolite has been identified in various biochemical contexts, such as in the yeast Saccharomyces cerevisiae, where it was discovered alongside other novel metabolites, indicating its involvement in metabolic pathways within this organism (PMID:36899826 ). Additionally, 4-guanidinobutanal has been detected in the granules of the traditional medicinal plant Isatidis Radix, suggesting its presence in natural product chemistry and potential implications in herbal medicine (PMID:36057409 ). The presence of this compound in diverse biological systems highlights its potential roles in metabolic processes, although specific pathways remain to be fully elucidated.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(4-Oxobutyl)guanidine	ChEBI

Molecular Formula

C₅H₁₁N₃O

Average Mass

129.163

Monoisotopic Mass

129.090211986

IUPAC Name

N-(4-oxobutyl)guanidine

Traditional Name

4-guanidinobutanal

CAS Registry Number

Not Available

SMILES

NC(=N)NCCCC=O

InChI Identifier

InChI=1S/C5H11N3O/c6-5(7)8-3-1-2-4-9/h4H,1-3H2,(H4,6,7,8)

InChI Key

VCOFTLCIPLEZKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Guanidine
Carboximidamide
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butanals (CHEBI:16671 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.55 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	16.93	ChemAxon
pKa (Strongest Basic)	12.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	45.25 m³·mol⁻¹	ChemAxon
Polarizability	13.72 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-4a06eaef72b2ad7d3de9	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-9300000000-c63f3cd099c1411421cb	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-5a5e020d5bf4b04eed87	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9600000000-d9f10fa87e4a02a770f2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9000000000-e4c4dc7c1586790e4ea7	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2414211a72ff5d067aac	2019-02-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	424.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	288.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	37.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	237.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (void)	2025-10-24	271.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	289.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	426.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	739.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	507.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	168.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	488.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	181.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	58.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	259.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	888.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	60.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	226.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (void)	2025-10-24	595.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	567.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	4-guanidinobutanal_TMS_1	C[Si](C)(C)OC=CCCNC(=N)N	standard non polar	2025-10-24	1850.15
Gas Chromatography	4-guanidinobutanal_TMS_2	C[Si](C)(C)NC(=N)NCCCC=O	standard non polar	2025-10-24	1657.6
Gas Chromatography	4-guanidinobutanal_TMS_3	C[Si](C)(C)N=C(N)NCCCC=O	standard non polar	2025-10-24	1661.06
Gas Chromatography	4-guanidinobutanal_TMS_4	C[Si](C)(C)N(CCCC=O)C(=N)N	standard non polar	2025-10-24	2295.87
Gas Chromatography	4-guanidinobutanal_TMS_5	C[Si](C)(C)NC(=N)NCCC=CO[Si](C)(C)C	standard non polar	2025-10-24	2218.2
Gas Chromatography	4-guanidinobutanal_TMS_6	C[Si](C)(C)OC=CCCN(C(=N)N)[Si](C)(C)C	standard non polar	2025-10-24	1986.63
Gas Chromatography	4-guanidinobutanal_TMS_7	C[Si](C)(C)N=C(N)NCCC=CO[Si](C)(C)C	standard non polar	2025-10-24	1663.49
Gas Chromatography	4-guanidinobutanal_TMS_8	C[Si](C)(C)N(C(=N)NCCCC=O)[Si](C)(C)C	standard non polar	2025-10-24	2320.93
Gas Chromatography	4-guanidinobutanal_TMS_9	C[Si](C)(C)N=C(NCCCC=O)N[Si](C)(C)C	standard non polar	2025-10-24	1544.56
Gas Chromatography	4-guanidinobutanal_TMS_10	C[Si](C)(C)NC(=N)N(CCCC=O)[Si](C)(C)C	standard non polar	2025-10-24	2104.18
Gas Chromatography	4-guanidinobutanal_TMS_11	C[Si](C)(C)N=C(N)N(CCCC=O)[Si](C)(C)C	standard non polar	2025-10-24	2357.32
Gas Chromatography	4-guanidinobutanal_TMS_12	C[Si](C)(C)OC=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1693.93
Gas Chromatography	4-guanidinobutanal_TMS_13	C[Si](C)(C)N=C(NCCC=CO[Si](C)(C)C)N[Si](C)(C)C	standard non polar	2025-10-24	2348.96
Gas Chromatography	4-guanidinobutanal_TMS_14	C[Si](C)(C)NC(=N)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1873.4
Gas Chromatography	4-guanidinobutanal_TMS_15	C[Si](C)(C)N=C(N)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1580.73
Gas Chromatography	4-guanidinobutanal_TMS_16	C[Si](C)(C)N=C(NCCCC=O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2262.95
Gas Chromatography	4-guanidinobutanal_TMS_17	C[Si](C)(C)N(CCCC=O)C(=N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1566.04
Gas Chromatography	4-guanidinobutanal_TMS_18	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC=O)[Si](C)(C)C	standard non polar	2025-10-24	2574.26
Gas Chromatography	4-guanidinobutanal_TMS_19	C[Si](C)(C)OC=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2391.35
Gas Chromatography	4-guanidinobutanal_TMS_20	C[Si](C)(C)N=C(NCCC=CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2210.98
Gas Chromatography	4-guanidinobutanal_TMS_21	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1931.18
Gas Chromatography	4-guanidinobutanal_TMS_22	C[Si](C)(C)N=C(N(CCCC=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	3143.91
Gas Chromatography	4-guanidinobutanal_TMS_23	C[Si](C)(C)N=C(N(CCC=CO[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1730.74
Gas Chromatography	4-guanidinobutanal_TMS_1	C[Si](C)(C)OC=CCCNC(=N)N	standard polar	2025-10-24	1840.38
Gas Chromatography	4-guanidinobutanal_TMS_2	C[Si](C)(C)NC(=N)NCCCC=O	standard polar	2025-10-24	2289.71
Gas Chromatography	4-guanidinobutanal_TMS_3	C[Si](C)(C)N=C(N)NCCCC=O	standard polar	2025-10-24	2123.34
Gas Chromatography	4-guanidinobutanal_TMS_4	C[Si](C)(C)N(CCCC=O)C(=N)N	standard polar	2025-10-24	2003.68
Gas Chromatography	4-guanidinobutanal_TMS_5	C[Si](C)(C)NC(=N)NCCC=CO[Si](C)(C)C	standard polar	2025-10-24	2113.37
Gas Chromatography	4-guanidinobutanal_TMS_6	C[Si](C)(C)OC=CCCN(C(=N)N)[Si](C)(C)C	standard polar	2025-10-24	2002.62
Gas Chromatography	4-guanidinobutanal_TMS_7	C[Si](C)(C)N=C(N)NCCC=CO[Si](C)(C)C	standard polar	2025-10-24	2213.31
Gas Chromatography	4-guanidinobutanal_TMS_8	C[Si](C)(C)N(C(=N)NCCCC=O)[Si](C)(C)C	standard polar	2025-10-24	2706.91
Gas Chromatography	4-guanidinobutanal_TMS_9	C[Si](C)(C)N=C(NCCCC=O)N[Si](C)(C)C	standard polar	2025-10-24	2293.67
Gas Chromatography	4-guanidinobutanal_TMS_10	C[Si](C)(C)NC(=N)N(CCCC=O)[Si](C)(C)C	standard polar	2025-10-24	2402.67
Gas Chromatography	4-guanidinobutanal_TMS_11	C[Si](C)(C)N=C(N)N(CCCC=O)[Si](C)(C)C	standard polar	2025-10-24	2280.91
Gas Chromatography	4-guanidinobutanal_TMS_12	C[Si](C)(C)OC=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2643.97
Gas Chromatography	4-guanidinobutanal_TMS_13	C[Si](C)(C)N=C(NCCC=CO[Si](C)(C)C)N[Si](C)(C)C	standard polar	2025-10-24	2093.39
Gas Chromatography	4-guanidinobutanal_TMS_14	C[Si](C)(C)NC(=N)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2071.63
Gas Chromatography	4-guanidinobutanal_TMS_15	C[Si](C)(C)N=C(N)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1802.55
Gas Chromatography	4-guanidinobutanal_TMS_16	C[Si](C)(C)N=C(NCCCC=O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2037.98
Gas Chromatography	4-guanidinobutanal_TMS_17	C[Si](C)(C)N(CCCC=O)C(=N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1886.09
Gas Chromatography	4-guanidinobutanal_TMS_18	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC=O)[Si](C)(C)C	standard polar	2025-10-24	2066.21
Gas Chromatography	4-guanidinobutanal_TMS_19	C[Si](C)(C)OC=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2009.6
Gas Chromatography	4-guanidinobutanal_TMS_20	C[Si](C)(C)N=C(NCCC=CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1886.83
Gas Chromatography	4-guanidinobutanal_TMS_21	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=CO[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1954.32
Gas Chromatography	4-guanidinobutanal_TMS_22	C[Si](C)(C)N=C(N(CCCC=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2451.3
Gas Chromatography	4-guanidinobutanal_TMS_23	C[Si](C)(C)N=C(N(CCC=CO[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1429.99

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02647

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16671

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 4-guanidinobutanal (MMDBc0054269)

MOL for #<Metabolite:0x00007f2df402f2a0>

3D MOL for #<Metabolite:0x00007f2df402f2a0>

3D SDF for #<Metabolite:0x00007f2df402f2a0>

3D-SDF for #<Metabolite:0x00007f2df402f2a0>

PDB for #<Metabolite:0x00007f2df402f2a0>

3D PDB for #<Metabolite:0x00007f2df402f2a0>

SMILES for #<Metabolite:0x00007f2df402f2a0>

INCHI for #<Metabolite:0x00007f2df402f2a0>

Structure for #<Metabolite:0x00007f2df402f2a0>

3D Structure for #<Metabolite:0x00007f2df402f2a0>