ECMDB: Ethylenediamine (ECMDB20274) (M2MDB001114)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)XML

Proteins (1004)

Record Information

Version

2.0

Creation Date

2012-05-31 14:36:39 -0600

Update Date

2015-07-07 10:42:07 -0600

Secondary Accession Numbers

ECMDB20274

Identification

Name:

Ethylenediamine

Description

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000,000 kg being produced in 1998.In terms of quantities produced, ethylenediamine is the most significant diamine (aside from diaminohexane, which is a precursor to Nylon 6-6). Related derivatives of ethylenediamine include tetramethylethylenediamine, abbreviated (TMEDA), (CH3)2N-CH2CH2-N(CH3)2 and tetraethylethylenediamine, abbreviated (TEEDA), (C2H5)2N-CH2CH2-N(C2H5)2The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil."

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1,2-Diamino-ethaan
1,2-Diamino-ethano
1,2-Diaminoaethan
1,2-Diaminoethane
1,2-Diaminoethane dihydrochloride
1,2-Ethanediamine
1,2-Ethanediamine, dihydrochloride
1,2-Ethylenediamine
1,2-ETHYLENEDIAMINE(HYDROCHLORIDE)
1,4-Butanediamine
1,4-Diaminobutane
Aethaldiamin
Aethylenediamin
b-Aminoethylamine
Beta-Aminoethylamine
Chlor-ethamine
Diaminoethane
Dimethylenediamine
Dimethylenediamine dihydrochloride
Dimethylenediamine diydrochloride
Ethane-1,2-diamine
Ethanediamine
Ethyleendiamine
Ethylendiamine
Ethylenediamine di HCL
Ethylenediamine dihydrochloride
Ethylenediamine hydrochloride (van)
Ethylenediamine, dihydrochloride
Ethylenediammonium chloride
Ethylenediammonium dichloride
H2NCH2CH2NH2
Putrescine
Tetramethylenediamine
β-Aminoethylamine

Chemical Formula:

C₂H₉N₂

Weight:

Average: 61.1063
Monoisotopic: 61.076573298

InChI Key:

PIICEJLVQHRZGT-UHFFFAOYSA-O

InChI:

InChI=1S/C2H8N2/c3-1-2-4/h1-4H2/p+1

CAS number:

333-18-6

IUPAC Name:

2-aminoethan-1-aminium

Traditional IUPAC Name:

2-aminoethanaminium

SMILES:

NCC[NH3+]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Liquid

Charge:

Melting point:

9 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	130 g/L	ALOGPS
logP	-3	ALOGPS
logP	-1.4	ChemAxon
logS	0.13	ALOGPS
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	29.16 m³·mol⁻¹	ChemAxon
Polarizability	7.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Hydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + Ethylenediamine
S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine
Adenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + Phosphate
Agmatine + Water <> Putrescine + Urea + Ethylenediamine
Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + Water
S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine
Hydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + Ethylenediamine
S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine

SMPDB Pathways:

Glutathione metabolism	PW000833
beta-Alanine metabolism	PW000896

KEGG Pathways:

ABC transporters ec02010
Arginine and proline metabolism ec00330
Cysteine and methionine metabolism ec00270
Glutathione metabolism ec00480
Metabolic pathways eco01100
beta-Alanine metabolism ec00410

EcoCyc Pathways:

Not Available

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
70± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-4985de1c5392d9cbd49c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-6fa8e4a5f9a4a9689d32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3393ca3f2cf9de78a66f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-14ea32757884af230295	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-c12a1fd0714f37802d9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9000000000-84423b037087f58ff30c	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	30347
HMDB ID	Not Available
Pubchem Compound ID	5063660
Kegg ID	C00134
ChemSpider ID	4240651
Wikipedia ID	Ethylenediamine
BioCyc ID	CPD-3682
EcoCyc ID	CPD-3682

Enzymes

Protein Details

1. Spermidine synthase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM), which serves as an aminopropyl donor
Gene Name:: speE
Uniprot ID:: P09158
Molecular weight:: 32321

Reactions

S-adenosylmethioninamine + putrescine = 5'-S-methyl-5'-thioadenosine + spermidine.

Protein Details

2. Spermidine N(1)-acetyltransferase

General function:: Involved in N-acetyltransferase activity
Specific function:: Regulates polyamine concentration by their degradation. Acts on spermidine, forming N(1)- and N(8)-acetylspermidine
Gene Name:: speG
Uniprot ID:: P0A951
Molecular weight:: 21887

Reactions

Acetyl-CoA + an alkane-alpha,omega-diamine = CoA + an N-acetyldiamine.

Protein Details

3. Ornithine decarboxylase, constitutive

General function:: Involved in carboxy-lyase activity
Specific function:: L-ornithine = putrescine + CO(2)
Gene Name:: speC
Uniprot ID:: P21169
Molecular weight:: 79416

Reactions

L-ornithine = putrescine + CO(2).

Protein Details

4. Ornithine decarboxylase, inducible

General function:: Involved in carboxy-lyase activity
Specific function:: L-ornithine = putrescine + CO(2)
Gene Name:: speF
Uniprot ID:: P24169
Molecular weight:: 82415

Reactions

L-ornithine = putrescine + CO(2).

Protein Details

5. Putrescine aminotransferase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the aminotransferase reaction from putrescine to 2-oxoglutarate, leading to glutamate and 4-aminobutanal, which spontaneously cyclizes to form 1-pyrroline. Is also able to transaminate cadaverine and, in lower extent, spermidine, but not ornithine. Alpha-ketobutyrate and pyruvate can also act as amino acceptors, although much less efficiently
Gene Name:: patA
Uniprot ID:: P42588
Molecular weight:: 49661

Reactions

Putrescine + 2-oxoglutarate = L-glutamate + 1-pyrroline + H(2)O.

Protein Details

6. Agmatinase

General function:: Involved in agmatinase activity
Specific function:: Catalyzes the formation of putrescine from agmatine
Gene Name:: speB
Uniprot ID:: P60651
Molecular weight:: 33557

Reactions

Agmatine + H(2)O = putrescine + urea.

Protein Details

7. Gamma-glutamylputrescine synthetase

General function:: Involved in glutamate-ammonia ligase activity
Specific function:: Involved in the breakdown of putrescine via the biosynthesis of gamma-L-glutamylputrescine
Gene Name:: puuA
Uniprot ID:: P78061
Molecular weight:: 53177

Reactions

ATP + L-glutamate + putrescine = ADP + phosphate + gamma-L-glutamylputrescine.

Ethylenediamine (ECMDB20274) (M2MDB001114)

Structure for #<Compound:0x97d986bc>

Enzymes

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