Compounds > s-adenosyl-3-thiopropylamine
Page last updated: 2024-12-08

s-adenosyl-3-thiopropylamine

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Description

S-adenosyl-3-thiopropylamine: decarboxylated S-adenosylhomocysteine; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

S-adenosyl-3-thiopropylamine : A thioadenosine that is adenosine in which the hydroxy group at C-5' is replaced by a 3-aminopropyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID171251
CHEMBL ID538693
CHEBI ID79030
SCHEMBL ID1398379
MeSH IDM0059947

Synonyms (18)

Synonym
chebi:79030 ,
CHEMBL538693 ,
bdbm50294572
(2r,3r,4s,5s)-2-(6-amino-9h-purin-9-yl)-5-((3-aminopropylthio)methyl)tetrahydrofuran-3,4-diol
5''-(aminopropylthio)-5''-deoxy-adenosine
(2s,3s,4r,5r)-2-(3-aminopropylsulfanylmethyl)-5-(6-aminopurin-9-yl)oxolane-3,4-diol
5'-s-(3-aminopropyl)-5'-thioadenosine
adenosine, 5'-s-(3-aminopropyl)-5'-thio-
s-adenosyl-3-thiopropylamine
53186-57-5
dcadohcy
dc-sah
SCHEMBL1398379
s-(5')-adenosyl-3-thiopropylamine
DTXSID50201247
mfcd17215932
s-(5'-adenosyl)-3-thiopropylamine, >=98.0% (hplc)
Q27148104
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
thioadenosine
organic sulfideCompounds having the structure RSR (R =/= H). Such compounds were once called thioethers.
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA (cytosine-5)-methyltransferase 1Homo sapiens (human)IC50 (µMol)45.00000.01861.64886.0000AID424255
Histone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)Ki100.00000.00000.06370.3000AID1054112; AID702374
DNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)IC50 (µMol)17.00000.20001.21647.5000AID424256
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
DNA methylation-dependent heterochromatin formationDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
DNA-templated transcriptionDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
positive regulation of gene expressionDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
negative regulation of gene expressionDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
methylationDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
epigenetic programming of gene expressionDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
negative regulation of gene expression via chromosomal CpG island methylationDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
cellular response to amino acid stimulusDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
chromosomal DNA methylation maintenance following DNA replicationDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
cellular response to bisphenol ADNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferationDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell apoptotic processDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell differentiation involved in phenotypic switchingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
positive regulation of cell population proliferationHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
gene expressionHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
heterochromatin formationHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
telomere organizationHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
methylationHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
regulation of receptor signaling pathway via JAK-STATHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
regulation of transcription regulatory region DNA bindingHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
DNA repairHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
DNA damage checkpoint signalingHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
positive regulation of gene expressionDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
methylationDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
DNA bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
RNA bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
DNA (cytosine-5-)-methyltransferase activityDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
protein bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
zinc ion bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
methyl-CpG bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
DNA-methyltransferase activityDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
promoter-specific chromatin bindingDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
nucleic acid bindingHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
DNA bindingHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
protein bindingHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
histone methyltransferase activityHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
histone H3 methyltransferase activityHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
histone H3K79 trimethyltransferase activityHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
histone H3K79 methyltransferase activityHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
transcription corepressor activityDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
DNA (cytosine-5-)-methyltransferase activityDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
protein bindingDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
DNA-methyltransferase activityDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
metal ion bindingDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
DNA (cytosine-5-)-methyltransferase activity, acting on CpG substratesDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
DNA bindingDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
female germ cell nucleusDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
nucleusDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
nucleoplasmDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
replication forkDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
pericentric heterochromatinDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
nucleusDNA (cytosine-5)-methyltransferase 1Homo sapiens (human)
nucleusHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
nucleoplasmHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
cytoplasmHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
intracellular membrane-bounded organelleHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
protein-containing complexHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
nucleusHistone-lysine N-methyltransferase, H3 lysine-79 specificHomo sapiens (human)
nucleusDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
nucleoplasmDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
catalytic complexDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
nucleusDNA (cytosine-5)-methyltransferase 3BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1192322Inhibition of N-terminally FLAG-tagged wild type EZH2 in EZH2/SUZ12/EED/RbAp48 complex (unknown origin) expressed in baculovirus infected in SF9 cells assessed as inhibition of methylation of nucleosomes at H3K27 at 20 uM by scintillation counting in pres2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
SAH derived potent and selective EZH2 inhibitors.
AID425816Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei LAB 110 EATRO after 48 hrs by Z1 zoulter counter2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID424256Inhibition of human recombinant DNMT3b22009Bioorganic & medicinal chemistry letters, May-15, Volume: 19, Issue:10
Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors.
AID422448Antitrypanosomal activity against diamidine and melarsoprol-resistant bloodstream form of Trypanosoma brucei brucei isolate KETRI 243-As10-3 after 48 hrs by Z1 zoulter counter2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID422446Antitrypanosomal activity against pentamidine and melarsoprol-resistant bloodstream form of Trypanosoma brucei brucei isolate KETRI 243 after 48 hrs by Z1 zoulter counter2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID1881231Binding affinity to full length human N-terminal his6-tagged DNMT2 expressed in Escherichia coli Rosetta2(DE3)pLysS at 100 uM incubated for 5 mins by microscale thermophoresis assay2022Journal of medicinal chemistry, 07-28, Volume: 65, Issue:14
Discovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment.
AID422447Antitrypanosomal activity against pentamidine-resistant bloodstream form of Trypanosoma brucei brucei isolate KETRI 269 after 48 hrs by Z1 zoulter counter2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID425817Activity at bloodstream Trypanosoma brucei brucei 5'-deoxy-5'-(methylthio)-adenosine phosphorylase by spectrophotometry relative to control2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID1054112Competitive inhibition of recombinant human DOT1L using adenosine/deazaadenosine as substrate and SAM cofactor2013Journal of medicinal chemistry, Nov-27, Volume: 56, Issue:22
A medicinal chemistry perspective for targeting histone H3 lysine-79 methyltransferase DOT1L.
AID702374Inhibition of human recombinant DOT1L catalytic domain amino acid (1 to 472) using [3H]-SAM after 30 mins by scintillation counter2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Synthesis and structure-activity relationship investigation of adenosine-containing inhibitors of histone methyltransferase DOT1L.
AID425815Activity at bloodstream Trypanosoma brucei brucei 5'-deoxy-5'-(methylthio)-adenosine phosphorylase by spectrophotometry in presence of 50 mM PO4- relative to control2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Novel trypanocidal analogs of 5'-(methylthio)-adenosine.
AID1881232Inhibition of full length human N-terminal his6-tagged DNMT2 expressed in Escherichia coli Rosetta2(DE3)pLysS at 100 uM using tRNA asp as substrate and SAM as co-substrate incubated for 5 mins by tritium incorporation assay relative to control2022Journal of medicinal chemistry, 07-28, Volume: 65, Issue:14
Discovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment.
AID424255Inhibition of human recombinant DNMT12009Bioorganic & medicinal chemistry letters, May-15, Volume: 19, Issue:10
Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (30.00)18.7374
1990's0 (0.00)18.2507
2000's2 (20.00)29.6817
2010's4 (40.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.27 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (10.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
putrescine
[no description available]		2.0610alkane-alpha,omega-diamineantioxidant;
fundamental metabolite
spermidine
[no description available]		2.0610polyazaalkane;
triamine		autophagy inducer;
fundamental metabolite;
geroprotector
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		1.9510adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
sinefungin
[no description available]		2.4110adenosines;
non-proteinogenic alpha-amino acid		antifungal agent;
antimicrobial agent
homocysteine
Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.		2.3620amino acid zwitterion;
homocysteine;
serine family amino acid		fundamental metabolite;
mouse metabolite
5-iodotubercidin
7-iodotubercidin: inhibits Toxoplasma gondii adenosine kinase		3.1810organoiodine compound
5'-methylthiotubercidin
[no description available]		2.0410
n(4)-adenosyl-n(4)-methyl-2,4-diaminobutanoic acid
[no description available]		2.5920
s-adenosylhomocysteine
S-Adenosylhomocysteine: 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions.. S-adenosyl-L-homocysteine : An organic sulfide that is the S-adenosyl derivative of L-homocysteine.		4.7290adenosines;
amino acid zwitterion;
homocysteine derivative;
homocysteines;
organic sulfide		cofactor;
EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor;
EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor;
epitope;
fundamental metabolite
5'-methylthioadenosine
5'-methylthioadenosine: structure. 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.		2.0410thioadenosinealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
s-adenosyl-3-methylthiopropylamine
S-adenosyl-3-methylthiopropylamine: decarboxylated S-adenosylmethionine		1.9510adenosines;
sulfonium compound		Escherichia coli metabolite;
human urinary metabolite;
mouse metabolite;
rat metabolite
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		1.9510organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
epz004777
[no description available]		3.1810N-glycosyl compound
epz-5676
[no description available]		3.18105'-deoxyribonucleoside
ConditionIndicatedRelationship StrengthStudiesTrials
Disease
A definite pathologic process with a characteristic set of signs and symptoms. It may affect the whole body or any of its parts, and its etiology, pathology, and prognosis may be known or unknown.		0310
Benign Neoplasms
[description not available]		02.4110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.4110