Molecule

Methylthioadenosine

AlkaPlorer ID: AK010640

Synonym: None

IUPAC Name: (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol

Structure

SMILES: CSC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O

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

Reference

Metabolic Profiling of <i>Escherichia coli</i>-Based Cell-Free Expression Systems for Process Optimization

PubChem CID: 439176

CAS: 2457-80-9

LOTUS: LTS0058305

SuperNatural Ⅲ: SN0420588-13

NPASS: NPC136349

{

NPAtlas: NPA008075

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Saccharomyces cerevisiae	Saccharomyces	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota
Glehnia littoralis	Glehnia	Apiaceae	Apiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Mus musculus	Mus	Muridae	Rodentia	Mammalia	Chordata	Metazoa	Eukaryota
Chlamydomonas reinhardtii	Chlamydomonas	Chlamydomonadaceae	Chlamydomonadales	Chlorophyceae	Chlorophyta	Viridiplantae	Eukaryota
Escherichia coli	Escherichia	Enterobacteriaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria
Pinellia ternata	Pinellia	Araceae	Alismatales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 297.34000000000003

TPSA？: 119.31000000000002

MolLogP？: -0.6093000000000002

Number of H-Donors: 3

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	Adenosine A2b receptor	Ki	8200.0	nM	10.1021/jm031092g
Homo sapiens	Adenosine A2b receptor	Ki	13900.0	nM	10.1021/jm031092g
Homo sapiens	Adenosine A2 receptor	Affinity constant	10.0	uM	10.1021/jm00345a001
Homo sapiens	Adenosine A3 receptor	Efficacy	46.0	%	10.1021/jm031092g
Homo sapiens	Adenosine A3 receptor	IC50	71000.0	nM	10.1021/jm031092g
Homo sapiens	Adenosine A3 receptor	Ki	680.0	nM	10.1021/jm031092g
Homo sapiens	Adenosine receptor	Affinity constant	nan	None	10.1021/jm00345a001
Homo sapiens	Adenosylhomocysteinase	Activity	48.0	%	10.1021/jm00112a039
Homo sapiens	Adenosylhomocysteinase	Activity	66.0	%	10.1021/jm00112a039
Homo sapiens	Adenosylhomocysteinase	Activity	86.0	%	10.1021/jm00112a039
Homo sapiens	Adenosylhomocysteinase	Activity	94.0	%	10.1021/jm00112a039
Homo sapiens	Adenosylhomocysteinase	Activity	101.0	%	10.1021/jm00112a039
Homo sapiens	Catechol O-methyltransferase	Ki	5400000.0	nM	10.1021/jm00143a002
Homo sapiens	CCRF-CEM	IC50	150000.0	nM	10.1021/jm00112a039
Homo sapiens	Fatty acid synthase	Ki	1500000.0	nM	10.1016/j.bmcl.2004.01.051
Homo sapiens	Indolethylamine N-methyltransferase	Ki	700000.0	nM	10.1021/jm00364a021
Homo sapiens	MOLT-4	IC50	11000.0	nM	10.1021/jm00112a039
Homo sapiens	PRMT5/MEP50 complex	Kd	661.0	nM	10.1021/acs.jmedchem.1c01900
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	K cat	0.0065	1/sec	10.1016/j.bmcl.2005.03.107
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	K cat	4.6	1/sec	10.1016/j.bmcl.2005.03.107
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	Km	4600.0	nM	10.1016/j.bmcl.2005.03.107
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	Km	5000.0	nM	10.1021/jm050269z
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	Km	106000.0	nM	10.1016/j.bmcl.2005.03.107
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	Ratio	0.0001	1/uM*sec	10.1016/j.bmcl.2005.03.107
Homo sapiens	S-methyl-5-thioadenosine phosphorylase	Ratio	3.2	1/uM*sec	10.1016/j.bmcl.2005.03.107
Mus musculus	L1210	Activity	0.19	None	10.1021/jm00112a039
Mus musculus	L1210	Activity	0.2	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L1210	Activity	1.22	None	10.1021/jm00112a039
Mus musculus	L1210	Activity	1.59	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L1210	Activity	1.93	None	10.1021/jm00112a039
Mus musculus	L1210	Activity	3.64	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L1210	Control	53.0	%	10.1021/jm00125a012
Mus musculus	L1210	IC50	600000.0	nM	10.1021/jm00125a012
Mus musculus	L1210	IC50	850000.0	nM	10.1021/jm00112a039
Mus musculus	L5178Y	Activity	0.43	None	10.1021/jm00112a039
Mus musculus	L5178Y	Activity	0.47	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L5178Y	Activity	1.24	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L5178Y	Activity	1.85	None	10.1021/jm00112a039
Mus musculus	L5178Y	Activity	2.79	None	10.1021/jm00112a039
Mus musculus	L5178Y	Activity	3.03	nM (10e6*cells)-1	10.1021/jm00125a012
Mus musculus	L5178Y	Control	57.0	%	10.1021/jm00125a012
Mus musculus	L5178Y	IC50	60000.0	nM	10.1021/jm00125a012
Mus musculus	L5178Y	IC50	200000.0	nM	10.1021/jm00112a039
Mus musculus	S-methyl-5-thioadenosine phosphorylase	Control	100.0	%	10.1021/jm00112a039
Mus musculus	S-methyl-5-thioadenosine phosphorylase	Km	1300.0	nM	10.1021/jm00112a039
Plasmodium falciparum	Spermidine synthase	IC50	159000.0	nM	10.1021/jm7016144
Rattus norvegicus	Adenosine A1 receptor	IC50	680.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A1 receptor	IC50	15100.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A1 receptor	Ki	150.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A1 receptor	Ki	210.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A1 receptor	Ki	240.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A1 receptor	Ratio	22.2	None	10.1021/jm031092g
Rattus norvegicus	Adenosine A2a receptor	Ki	1130.0	nM	10.1021/jm031092g
Rattus norvegicus	Adenosine A2a receptor	Ki	1180.0	nM	10.1021/jm031092g
Rattus norvegicus	Spermidine synthase	Activity	9.0	%	10.1021/jm00137a014
Rattus norvegicus	Spermidine synthase	Activity	12.0	%	10.1021/jm00137a014
Rattus norvegicus	Spermidine synthase	Activity	41.0	%	10.1021/jm00137a014
Rattus norvegicus	Spermidine synthase	Activity	44.0	%	10.1021/jm00137a014
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)	5-methylthioadenosine/S-adenosylhomocysteine deaminase	Kcat	7.2	/s	10.1038/nature05981
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)	5-methylthioadenosine/S-adenosylhomocysteine deaminase	Kcat/Km	1.5	10^5/M/s	10.1038/nature05981
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)	5-methylthioadenosine/S-adenosylhomocysteine deaminase	Km	44000.0	nM	10.1038/nature05981
Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	100000.0	nM	10.1128/aac.00480-07
Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	nan	None	10.1128/aac.00480-07
None	Unchecked	Activity	100.0	%	10.1128/aac.00480-07
None	Unchecked	Activity	nan	None	10.1016/j.bmc.2007.11.075
None	Unchecked	Inhibition	nan	%	10.1021/jm3001532

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000296	C(=O)OCC(COCCC(N)C(=O)O)OC()=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR173654
AKRT000330	C(=O)OC[C@H](COCCC(N)C(=O)O)OC()=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR176371
AKRT000446	*C(=O)[C@H](CC[S@+](C)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O)NC(=O)CC(=O)CC[C@H](C)NC(=O)[C@@H](CC(N)=O)NC(=O)CCCCCCCCCCCCC>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-21115
AKRT000569	NC(=O)[C@H](Cc1c[nH]c(CC[C@H](N)C(=O)O)n1)NC()=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR176003
AKRT000833	OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(=O)n(CC[C@H](N)C(=O)O)c2=O)[C@H](O)[C@@H]1OP(=O)(O)O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR174169
AKRT007369	CCCC(=O)CC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10022
AKRT007383	CCCC(=O)N[C@@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR133123
AKRT007385	CCCC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10024
AKRT007876	CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10020
AKRT008091	CCCCCCCC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10025
AKRT008455	CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10023
AKRT010189	CC[C@H](N)C(=O)O.C[SAH]>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	enzymemap_40528
AKRT012615	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.C[C@@H](O)CC(=O)N[C@H]1CCOC1=O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-10026
AKRT012616	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NCCCCNCCCN.O=C=O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR137342
AKRT012617	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@@H](CCOc1ccc(/C(=N/O)C(=O)N[C@H]2CN([C@@H](C(=O)O)c3ccc(O)cc3)C2=O)cc1)C(=O)O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR147999
AKRT012618	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@@H](O)[C@@H](O)[C@@H](O)C=O	MNXR191996
AKRT012619	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1OC(O)[C@H](O)[C@@H]1O	METHYLTHIOADENOSINE-NUCLEOSIDASE-RXN
AKRT012620	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O	RXN-10035
AKRT012621	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)[C@H](O)[C@@H]1O	25025
AKRT012622	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@H](OP(=O)(O)O)[C@H](O)[C@@H]1O	5-METHYLTHIOADENOSINE-PHOSPHORYLASE-RXN
AKRT012623	CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>Nc1ncnc2[nH]cnc12	5-METHYLTHIOADENOSINE-PHOSPHORYLASE-RXN
AKRT012672	C[33S]>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.NC1(C(=O)O)CC1	None
AKRT014502	C[S+](CCCN)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-15699
AKRT014511	C[S+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	R00075
AKRT014532	C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	RXN-14518
AKRT014772	C[S](CCC(=O)C(=O)O)CC1OC(n2cnc3c(N)ncnc32)C(O)C1O>>CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR154643