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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:23 UTC

Update Date

2023-02-21 17:18:51 UTC

HMDB ID

HMDB0029598

Secondary Accession Numbers

HMDB29598

Metabolite Identification

Common Name

Metenamine

Description

Metenamine, also known as hexamine or HMT, belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions. Metenamine is a drug which is used for prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. this drug is not used to treat infection and should only be used after appropriate eradication of infection with antimicrobial agents. Based on a literature review a small amount of articles have been published on Metenamine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane	ChEBI
Hexamethylenamine	ChEBI
Hexamethylene tetramine	ChEBI
Hexamethylentetramin	ChEBI
Hexamethylentetraminum	ChEBI
Hexamine	ChEBI
Hexaminum	ChEBI
HMT	ChEBI
HMTA	ChEBI
Metenamina	ChEBI
Methenamine	ChEBI
Methenaminum	ChEBI
Uritone	ChEBI
Urotropin	ChEBI
1,3,5,7-Tetraazaadamantane	HMDB
1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane	HMDB
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane	HMDB
1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane hydroiodide	HMDB
1,3,5,7-Tetraazatricyclo[3.3.1.13,7 ]decane	HMDB
1,3,5,7-Tetraazatricyclo[3.3.1.1~3,7~]decane	HMDB
Aceto HMT	HMDB
Aminoform	HMDB
Aminoformaldehyde	HMDB
Ammoform	HMDB
Ammonioformaldehyde	HMDB
Antihydral	HMDB
Carin	HMDB
Cystamin	HMDB
Cystogen	HMDB
Duirexol	HMDB
e239	HMDB
Ekagom H	HMDB
Esametilentetramina	HMDB
Formaldehyde-ammonia 6:4	HMDB
Formamine	HMDB
Formin	HMDB
Formin (heterocycle)	HMDB
Formin (the heterocyclic compound)	HMDB
Grasselerator 102	HMDB
H.m.t.	HMDB
Herax uts	HMDB
Heterin	HMDB
HEX	HMDB
Hexa	HMDB
Hexa (vulcanization accelerator)	HMDB
Hexa-flo-pulver	HMDB
Hexaform	HMDB
Hexaloids	HMDB
Hexamethylamine	HMDB
Hexamethyleneamine	HMDB
Hexamethylenetetraamine	HMDB
Hexamethylenetetramine	HMDB
Hexamethylenetetramine (aliphatic)	HMDB
Hexamethylenetetramine, 8ci	HMDB
Hexamethylenetetramine, acs	HMDB
Hexamethylenetetramine-palladium chloride adduct	HMDB
Hexamethylenetetraminum	HMDB
Hexamethylentetramine	HMDB
Hexamine (heterocycle)	HMDB
Hexamine silver	HMDB
Hexasan	HMDB
Hexilmethylenamine	HMDB
Mandelamine	HMDB
Methamin	HMDB
Methenamin	HMDB
Methenamine silver	HMDB
Metramine	HMDB
Naphthamine	HMDB
Natasol fast orange GR salt	HMDB
Nocceler H	HMDB
Preparation af	HMDB
Resotropin	HMDB
S 4 (Heterocycle)	HMDB
Sanceler H	HMDB
Silver methenamine	HMDB
Tetraazaadamantane	HMDB
Uramin	HMDB
Uratrine	HMDB
Urisol	HMDB
Uro-phosphate	HMDB
Urodeine	HMDB
Urotropine	HMDB
Vesaloin	HMDB
Vesalvine	HMDB
Vulkacit H 30	HMDB
Vulkacit H30	HMDB
Xametrin	HMDB
[16]-Adamazane, inn	HMDB
Methenamine, silver	HMDB
Silver, hexamine	HMDB
Silver, methenamine	HMDB

Chemical Formula

C₆H₁₂N₄

Average Molecular Weight

140.1863

Monoisotopic Molecular Weight

140.106196404

IUPAC Name

1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane

Traditional Name

1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane

CAS Registry Number

100-97-0

SMILES

C1N2CN3CN1CN(C2)C3

InChI Identifier

InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2

InChI Key

VKYKSIONXSXAKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Triazinanes

Sub Class

1,3,5-triazinanes

Direct Parent

1,3,5-triazinanes

Alternative Parents

Substituents

1,3,5-triazinane
Azacycle
Aminal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

polycyclic cage (CHEBI:6824 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029598)
Cytoplasm (HMDB: HMDB0029598)

Source

Exogenous

Exogenous (HMDB: HMDB0029598)

Food

Food (HMDB: HMDB0029598)

Endogenous

Endogenous (HMDB: HMDB0029598)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029598)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	449 mg/mL at 12 °C	Not Available
LogP	-4.150 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	126.842	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001005

Predicted Molecular Properties

Property	Value	Source
Water Solubility	766 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	0.39	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Basic)	5.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.96 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37 m³·mol⁻¹	ChemAxon
Polarizability	14.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	129.859	31661259
DarkChem	[M-H]-	124.313	31661259
DeepCCS	[M+H]+	129.773	30932474
DeepCCS	[M-H]-	127.497	30932474
DeepCCS	[M-2H]-	163.437	30932474
DeepCCS	[M+Na]+	138.052	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	125.9	32859911
AllCCS	[M+NH4]+	134.6	32859911
AllCCS	[M+Na]+	135.8	32859911
AllCCS	[M-H]-	127.4	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	129.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.04 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2392 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	74.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2318.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	530.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	381.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	568.9 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	569.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	159.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1113.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	406.0 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	1362.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	671.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	409.9 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	160.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metenamine	C1N2CN3CN1CN(C2)C3	2025.2	Standard polar	33892256
Metenamine	C1N2CN3CN1CN(C2)C3	1211.0	Standard non polar	33892256
Metenamine	C1N2CN3CN1CN(C2)C3	1163.3	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 - Metenamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-37095c7b831e11e5eee2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metenamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9300000000-e762ea01823717c4bda9	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metenamine LC-ESI-QQ , positive-QTOF	splash10-0006-0900000000-05c8e159897335060443	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metenamine LC-ESI-QQ , positive-QTOF	splash10-01ox-2900000000-86fe33e31cc8f7108c14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metenamine LC-ESI-QQ , positive-QTOF	splash10-01ti-9300000000-7eb44254c8cc65c09acd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metenamine LC-ESI-QQ , positive-QTOF	splash10-004i-9000000000-fd4edf8f48f9c42bca0c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metenamine LC-ESI-QQ , positive-QTOF	splash10-004l-9000000000-371b89c99afba4931848	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 10V, Positive-QTOF	splash10-0006-0900000000-fdd6b719cb07e4102442	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 20V, Positive-QTOF	splash10-0006-0900000000-fdd6b719cb07e4102442	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 40V, Positive-QTOF	splash10-0006-0900000000-fdd6b719cb07e4102442	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 10V, Negative-QTOF	splash10-000i-0900000000-4c20ce3a6256ce9cf869	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 20V, Negative-QTOF	splash10-000i-0900000000-4c20ce3a6256ce9cf869	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 40V, Negative-QTOF	splash10-000i-0900000000-4c20ce3a6256ce9cf869	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 10V, Negative-QTOF	splash10-000i-0900000000-df90583457c277060500	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 20V, Negative-QTOF	splash10-000i-0900000000-df90583457c277060500	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 40V, Negative-QTOF	splash10-000i-0900000000-df90583457c277060500	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 10V, Positive-QTOF	splash10-0006-0900000000-96b1ccc7b2dbac963a64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 20V, Positive-QTOF	splash10-0006-0900000000-96b1ccc7b2dbac963a64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metenamine 40V, Positive-QTOF	splash10-0006-0900000000-96b1ccc7b2dbac963a64	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

DB06799

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000762

KNApSAcK ID

Not Available

Chemspider ID

3959

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methenamine

METLIN ID

Not Available

PubChem Compound

4101

PDB ID

Not Available

ChEBI ID

6824

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1250041

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Metenamine (HMDB0029598)

MOL for HMDB0029598 (Metenamine)

3D MOL for HMDB0029598 (Metenamine)

3D SDF for HMDB0029598 (Metenamine)

3D-SDF for HMDB0029598 (Metenamine)

PDB for HMDB0029598 (Metenamine)

3D PDB for HMDB0029598 (Metenamine)

SMILES for HMDB0029598 (Metenamine)

INCHI for HMDB0029598 (Metenamine)

Structure for HMDB0029598 (Metenamine)

3D Structure for HMDB0029598 (Metenamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra