P. aeruginosa Metabolome Database: S-Adenosylmethioninamine (PAMDB000216)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000216

Identification

Name:

S-Adenosylmethioninamine

Description:

S-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt
(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt
3-amino-propyl-S-adenosine
3-Amino-propyl-S-adenosine
S-adenosylmethioninamine
S-methyl-S-adenosyl homocysteamine
DAdoMet
DcSAM
Decarboxylated AdoMet
Decarboxylated S-adenosylmethionine
Decarboxylated SAM
S-Adenosyl-(5')-3-methylthiopropylamine
S-Adenosyl-L-methioninamine
S-Adenosylmethioninamine
S-Methyl-S-adenosyl homocysteamine

Chemical Formula:

C₁₄H₂₃N₆O₃S

Average Molecular Weight:

355.436

Monoisotopic Molecular Weight:

355.155234322

InChI Key:

ZUNBITIXDCPNSD-LSRJEVITSA-N

InChI:

InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1

CAS number:

22365-13-5

IUPAC Name:

{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium

Traditional IUPAC Name:

decarboxylated sam

SMILES:

C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
6-aminopurine
Purine
Imidazopyrimidine
Aminopyrimidine
Imidolactam
Pyrimidine
Primary aromatic amine
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Oxolane
Imidazole
Azole
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonium compound (CHEBI:15625 )
adenosines (CHEBI:15625 )
Biogenic amines (C01137 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	1.27 mg/mL	ALOGPS
logP	0.28	ALOGPS
logP	-2.8	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	10.09	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.4 m³·mol^-1	ChemAxon
Polarizability	36.97 Å³	ChemAxon
Number of Rings	3	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:

S-Adenosylmethionine + Hydrogen ion <> S-Adenosylmethioninamine + Carbon dioxide
S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + Spermidine
Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine
S-Adenosylmethioninamine + Putrescine <> 5'-Methylthioadenosine + Spermidine
S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine
S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine
Putrescine + S-Adenosylmethioninamine > Hydrogen ion + Spermidine + 5'-Methylthioadenosine
S-adenosyl-L-methionine + Hydrogen ion > Carbon dioxide + S-Adenosylmethioninamine
Putrescine + S-Adenosylmethioninamine > Spermidine + Hydrogen ion + 5'-S-methyl-5'-thioadenosine

Pathways:

Arginine and proline metabolism pae00330
Cysteine and methionine metabolism pae00270
Glutathione metabolism pae00480
Metabolic pathways pae01100
beta-Alanine metabolism pae00410

Spectra

Spectra:

References

References:

Fontecave, M., Atta, M., Mulliez, E. (2004). "S-adenosylmethionine: nothing goes to waste." Trends Biochem Sci 29:243-249. Pubmed: 15130560
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Pegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15625
HMDB ID	HMDB00988
Pubchem Compound ID	1078
Kegg ID	C01137
ChemSpider ID	388529
Wikipedia ID	Not Available
BioCyc ID	S-ADENOSYLMETHIONINAMINE
EcoCyc ID	S-ADENOSYLMETHIONINAMINE

S-Adenosylmethioninamine (PAMDB000216)

Structure for S-Adenosylmethioninamine (PAMDB000216)