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CHEBI:234322 - methylthioadenosine-DADMe immucillin-A

ChEBI IDCHEBI:234322
ChEBI Namemethylthioadenosine-DADMe immucillin-A
Stars
DefinitionA pyrrolopyrimidine that is 5H-pyrrolo[3,2-d]pyrimidin-4-amine substituted by a {(3R,4S)-3-hydroxy-4-[(methylsulfanyl)methyl]pyrrolidin-1-yl}methyl group at position 7. It is a potent inhibitor of human 5'-methylthioadenosine phosphorylase (Ki = 86 pM) with anti-tumour activity.
Secondary ChEBI IDCHEBI:45867
Last Modified4 September 2025
Submitterrnash
DownloadsMolfile
FormulaC13H19N5OS
Net Charge0
Average Mass293.396
Monoisotopic Mass293.13103
SMILESCSC[C@H]1CN(Cc2cnc3c(N)ncnc23)C[C@@H]1O
InChIInChI=1S/C13H19N5OS/c1-20-6-9-4-18(5-10(9)19)3-8-2-15-12-11(8)16-7-17-13(12)14/h2,7,9-10,15,19H,3-6H2,1H3,(H2,14,16,17)/t9-,10+/m1/s1
InChIKeyNTHMDFGHOCNNOE-ZJUUUORDSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
EC 2.4.2.28 (S-methyl-5'-thioadenosine phosphorylase) inhibitor  An EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of S-methyl-5'-thioadenosine phosphorylase (EC 2.4.2.28).
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) has role antineoplastic agent (CHEBI:35610)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) has role apoptosis inducer (CHEBI:68495)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) has role EC 2.4.2.28 (S-methyl-5'-thioadenosine phosphorylase) inhibitor (CHEBI:235466)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a aromatic amine (CHEBI:33860)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a methyl sulfide (CHEBI:86315)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a monohydroxypyrrolidine (CHEBI:46777)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a pyrrolopyrimidine (CHEBI:38670)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a secondary alcohol (CHEBI:35681)
methylthioadenosine-DADMe immucillin-A (CHEBI:234322) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol
Synonyms  Source
MTDIASUBMITTER
methylthio-DADMe-immucillin ASUBMITTER
(3R,4S)-1-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-ylmethyl)-4-methylsulfanylmethyl-pyrrolidin-3-olSUBMITTER
MT-DADMe-ImmAChEBI
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(methylthio)methyl]-3-pyrrolidinolChEBI
methylthio-DADMe-immucillin-AChEBI
Manual XrefsDatabases
TDIPDBeChem
DB08606DrugBank
Registry NumbersSources
CAS:653592-04-2IUBMB
Citations