CAS 2457-80-9|Methylthioadenosine|5′-Deoxy-5′-(methylthio)adenosine|methylthioadenosine|(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol|MTA|5'-(Methylthio)adenos...

General Information

Structure

Molecular Formula

C₁₁H₁₅N₅O₃S

Molecular Mass

297.3335

Exact Mass

297.08956037

Charge

0

InChI

InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1

InChIKey

WUUGFSXJNOTRMR-IOSLPCCCSA-N

Canonic Smiles

CSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N

Isomeric Smiles

CSC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-0.61

LogD (pH = 5.5)

-0.73

Log P

-0.61

Rotatable Bonds

3

H Donor

3

H Acceptors

7

Lipinski's Rule of Five

true

Acid pKa

5.02

Polar Surface Area

119.31

Polarizability

29.26

Molar Refractivity

74.03

LOG S

-2.27

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

Methylthioadenosine5′-Deoxy-5′-(methylthio)adenosineMTA5'-(Methylthio)adenosine1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-β-D-ribofuranoseVitamin L25'-(Methylthio)-5'-deoxyadenosine5'-S-Methyl-5'-thioadenosineNSC 3354225'-Deoxy-5'-(methylthio)adenosine5'-Deoxy(methylthio)adenosine5'-S-Methyl-5'-thioadenosine5'-S-Methylthioadenosine5'-MethylthioadenosineS-methyl-5'-thioadenosineThiomethyladenosine5'-S-methyl-5'-thioadenosineMTAMethylthioadenosineS-Methyl-5'-thioadenosine9-(5-S-methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine5'-Methylthioadenosine5'-Deoxy-5'-(methylthio)adenosine5-Methylthioadenosine

IUPAC Traditional name

methylthioadenosine 5-methylthioadenosine

IUPAC name

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

Names and Identifiers

Registration numbers

Beilstein Number

42420

PubChem SID

248939151622284798145510

CAS Number

2457-80-9

MDL Number

MFCD00010533

PubChem CID

439176

UniProt Database

C1EPN0A5F5R2A1WZR2Q8XMY8B5BL97Q8Z9E2B8F704A8FSA3B4TXR1B7JL13B9DNJ2Q92BL9Q5HNU8B0BRW3B7MBE2

EnzymePortal Database

Q2LUH4A7ZHQ1O24915Q10DK7Q7VDN6Q9YAQ8B6EKZ7Q2FRU6A6VH76Q9ZMY2B8FRL9Q2RJW1B6YUF8Q8PUQ3F6X2V8

BRENDA Database

2.3.1.2284.1.1.172.5.1.43.5.4.403.2.2.92.5.1.1282.1.1.332.1.1.82.4.2.12.1.1.1002.5.1.1142.4.2.442.3.1.2294.4.1.B4

MetaboLights Database

MTBLS4012MTBLS452MTBLS1115MTBLS312MTBLS3725MTBLS3627MTBLS2205MTBLS4618MTBLS2878MTBLS180MTBLS1033MTBLS1801MTBLS4365MTBLS4366MTBLS3306

SABIO-RK Database

1642390873230921593700927331410414985197415941219070101420514103

Rhea Database

RHEA:16481RHEA:30515RHEA:42864RHEA:19973RHEA:42880RHEA:42868RHEA:49708RHEA:21744RHEA:23244RHEA:37471RHEA:13617RHEA:63292RHEA:12300RHEA:42872RHEA:36487RHEA:33387

BKMS React Database

4561430958113296511313618310184611831440205293740034847

IntEnz Database

EC 3.5.4.31EC 2.5.1.114EC 3.2.2.16EC 2.3.1.229EC 2.5.1.79EC 2.3.1.228EC 4.4.1.14EC 2.5.1.n7EC 3.2.2.9EC 2.5.1.126EC 2.5.1.23EC 2.5.1.22EC 2.5.1.4

BRENDA Ligand Database

293734847505315113402051183143648101846136183128131132968019157830958

HMDB Database

HMDB0001173

PubMed Citation Links

22735334

Reactom Database

R-HSA-8868783R-HSA-351215R-HSA-1237160R-HSA-5358494R-HSA-6782893R-HSA-351210

CHEBI ID

CHEBI:12771CHEBI:20494CHEBI:12055CHEBI:20491CHEBI:12064CHEBI:1986CHEBI:17509CHEBI:1966CHEBI:18175CHEBI:14605CHEBI:44181

NMRShiftDB Database

20231623

VirtualMetabolicHuman Database

Reaxys Registry

CHEMBL

SureChEMBL Database

CompTox Database

MetaCyc Database

5-METHYLTHIOADENOSINE

KEGG ID

C00170

DrugBank ID

DB02282

BindingDB Database

22111

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... ADORA2B(136), ADORA3(140)mouse ... Mtap(66902)rat ... Adora1(29290), Adora2a(25369)

Safety Information

GHS Hazard statements

H302

RTECS

AU7410000

Storage Temperature

-20°C

German water hazard class

3

GHS Pictograms

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

GHS Signal Word

Warning

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Physical Property

Apperance

Powder

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

TRC

D242600

5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethi

Sigma Aldrich

D5011

Application
5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways. Methylthioadenosine is used in studies on bacterial quorum sensing pathways that envolve enzymes such as 5′-Methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTAN).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D5011.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:17509

Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.

Molecule Details

References

PubChem Literature

From Data Sources

• Hartmann, S., et al.: Clin. Chem., 52, 1127 (1969)

• Olopade, O., et al.: Cancer Res., 53, 2410 (1969)

• Penner, N., et al.: J. Pharm. Biomed. Anal., 52, 534 (1969)

• Pegg, A., et al.: Biochem. J., 115, 241 (1969)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:134202