Molecule

Deoxyadenosine

AlkaPlorer ID: AK012799

Synonym: None

IUPAC Name: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

Structure

SMILES: NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1

InChI: InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1

InChIKey: OLXZPDWKRNYJJZ-RRKCRQDMSA-N

Reference

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

PubChem CID: 172885164

CAS: 16373-93-6

LOTUS: LTS0010529

SuperNatural Ⅲ: SN0269101-06

NPASS: NPC209525

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Fritillaria verticillata	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Homo sapiens	Homo	Hominidae	Primates	Mammalia	Chordata	Metazoa	Eukaryota
Fritillaria taipaiensis	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Euryale ferox	Euryale	Nymphaeaceae	Nymphaeales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Saccharomyces cerevisiae	Saccharomyces	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota
Linum usitatissimum	Linum	Linaceae	Malpighiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Fritillaria przewalskii	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Fritillaria cirrhosa	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Mus musculus	Mus	Muridae	Rodentia	Mammalia	Chordata	Metazoa	Eukaryota
Fritillaria unibracteata	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Ganoderma sinense	Ganoderma	Polyporaceae	Polyporales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Ganoderma lucidum	Ganoderma	Polyporaceae	Polyporales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Escherichia coli	Escherichia	Enterobacteriaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria
Fritillaria delavayi	Fritillaria	Liliaceae	Liliales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 251.246

TPSA？: 119.31000000000002

MolLogP？: -0.9508000000000004

Number of H-Donors: 3

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bos taurus	Adenosine deaminase	Km	31000.0	nM	10.1016/s0960-894x(99)00639-3
Bos taurus	Adenosine deaminase	Ratio	11.4	None	10.1016/s0960-894x(99)00639-3
Bos taurus	Adenosine deaminase	Relative Vmax	122.0	None	10.1016/s0960-894x(99)00639-3
Bos taurus	Adenosine deaminase	Vmax	353.0	uM min-1 (mg of protein)-1	10.1016/s0960-894x(99)00639-3
Canis lupus familiaris	MDCK	MIC	200.0	ug.mL-1	10.1021/jm00035a010
Coxsackievirus B4	Coxsackievirus B4	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Duck hepatitis B virus	Duck hepatitis B virus	Activity	40.0	%	10.1021/jm100803c
Hepatitis B virus	Hepatitis B virus	Activity	36.0	%	10.1021/jm100803c
Homo sapiens	Adenosine A1 receptor	Inhibition	5.0	%	10.1016/j.ejmech.2021.113607
Homo sapiens	Adenosine A2a receptor	Inhibition	2.0	%	10.1016/j.ejmech.2021.113607
Homo sapiens	Adenosine A2b receptor	Inhibition	12.0	%	10.1016/j.ejmech.2021.113607
Homo sapiens	Adenosine A3 receptor	Inhibition	5.0	%	10.1016/j.ejmech.2021.113607
Homo sapiens	ATH-8 cell line	ED50	100.0	uM	10.1021/jm00391a003
Homo sapiens	ATH-8 cell line	ID50	100.0	uM	10.1021/jm00391a003
Homo sapiens	Deoxycytidine kinase	Kcat	0.37	/s	10.1021/jm800134t
Homo sapiens	Deoxycytidine kinase	Kcat	2.1	/s	10.1021/jm800134t
Homo sapiens	Deoxycytidine kinase	Km	8500.0	nM	10.1021/jm800134t
Homo sapiens	Deoxycytidine kinase	Km	115000.0	nM	10.1021/jm800134t
Homo sapiens	Deoxycytidine kinase	Ratio	0.0182	/s/microM	10.1021/jm800134t
Homo sapiens	Deoxycytidine kinase	Ratio	0.0435	/s/microM	10.1021/jm800134t
Homo sapiens	DU-145	IC50	250000.0	nM	10.1039/C3MD00159H
Homo sapiens	HaCaT	IC50	250000.0	nM	10.1039/C3MD00159H
Homo sapiens	HEL	MIC	100.0	ug.mL-1	10.1021/jm00035a010
Homo sapiens	HeLa	MIC	200.0	ug.mL-1	10.1021/jm00035a010
Homo sapiens	MCF7	IC50	250000.0	nM	10.1039/C3MD00159H
Homo sapiens	MT4	CD50	100.0	uM	10.1021/jm00118a033
Homo sapiens	MT4	Protection	10.0	%	10.1021/jm00391a003
Homo sapiens	MT4	Toxicity	10.0	%	10.1021/jm00391a003
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	112.32	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	106.41	%	10.1124/mol.112.084152
Homo sapiens	Thymidine kinase, cytosolic	Activity	nan	None	10.1021/jm00100a029
Homo sapiens	Thymidine kinase, cytosolic	ID50	1000.0	uM	10.1021/jm00100a029
Human alphaherpesvirus 1	Human alphaherpesvirus 1	MIC	150.0	ug.mL-1	10.1021/jm00102a010
Human alphaherpesvirus 1	Human alphaherpesvirus 1	MIC	400.0	ug.mL-1	10.1021/jm00035a010
Human alphaherpesvirus 2	Human alphaherpesvirus 2	MIC	100.0	ug.mL-1	10.1021/jm00102a010
Human immunodeficiency virus 1	Human immunodeficiency virus 1	ED50	100.0	uM	10.1021/jm00118a033
Human immunodeficiency virus 1	Human immunodeficiency virus 1	MIC	20.0	ug.mL-1	10.1021/jm00102a010
Human respirovirus 3	Human respirovirus 3	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Mammalian orthoreovirus 1	Mammalian orthoreovirus 1	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Poliovirus 1	Poliovirus 1	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Rattus norvegicus	Adenosine A1 receptor	Displacement	31.0	%	10.1021/jm00007a014
Rattus norvegicus	Adenosine A1 receptor	Ki	23300.0	nM	10.1021/jm00020a014
Rattus norvegicus	Adenosine A2a receptor	Displacement	39.0	%	10.1021/jm00007a014
Rattus norvegicus	Adenosine A3 receptor	Displacement	28.0	%	10.1021/jm00007a014
Rattus norvegicus	Adenylate cyclase type V	IC50	15000.0	nM	10.1021/jm0303599
Rattus norvegicus	C6	IC50	250000.0	nM	10.1039/C3MD00159H
Rattus norvegicus	L6	IC50	250000.0	nM	10.1039/C3MD00159H
Respiratory syncytial virus	Respiratory syncytial virus	MIC	20.0	ug.mL-1	10.1021/jm00035a010
Semliki Forest virus	Semliki Forest virus	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Sindbis virus	Sindbis virus	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Staphylococcus aureus	Deoxyadenosine kinase	Kcat	1.82	/s	10.1128/aac.00081-07
Staphylococcus aureus	Deoxyadenosine kinase	Kcat/Km	6.22	10'4/M/s	10.1128/aac.00081-07
Staphylococcus aureus	Deoxyadenosine kinase	Km	29200.0	nM	10.1128/aac.00081-07
Staphylococcus aureus	Deoxyadenosine kinase	Vmax	4.1	U/mg	10.1128/aac.00081-07
Trichomonas vaginalis	Trichomonas vaginalis	GI	48.7	%	10.1016/j.bmcl.2012.03.087
Vaccinia virus	Vaccinia virus	MIC	150.0	ug.mL-1	10.1021/jm00102a010
Vaccinia virus	Vaccinia virus	MIC	400.0	ug.mL-1	10.1021/jm00035a010
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	200.0	ug.mL-1	10.1021/jm00102a010
Vesicular stomatitis virus	Vesicular stomatitis virus	MIC	400.0	ug.mL-1	10.1021/jm00035a010
Woodchuck hepatitis virus	Woodchuck hepatitis virus	Activity	1.5	None	10.1128/aac.00325-07
None	ADMET	CC50	nan	None	10.1021/jm100803c
None	ADMET	MIC	400.0	ug.mL-1	10.1021/jm00035a010
None	ESM	MIC	400.0	ug.mL-1	10.1021/jm00035a010
None	No relevant target	Drug metabolism	0.96	L/mol/min	10.1021/acs.jmedchem.1c00790
None	No relevant target	P	0.283	None	10.1021/jm00128a017
None	Unchecked	IC50	30.0	nM	10.1021/jm00146a020
None	Unchecked	IC50	180000.0	nM	10.1021/jm00146a020
None	Unchecked	Inhibition	13.0	%	10.1016/j.bmc.2009.03.028
None	Unchecked	Inhibition	29.0	%	10.1021/jm9006356
None	Unchecked	Inhibition	nan	%	10.1128/aac.00425-07
None	Unchecked	Kcat	0.24	/s	10.1021/jm800134t
None	Unchecked	Kcat	1.9	/s	10.1021/jm800134t
None	Unchecked	Ki	230.0	nM	10.1128/aac.00425-07
None	Unchecked	Ki	11000.0	nM	10.1021/jm9006356
None	Unchecked	Ki	100000.0	nM	10.1021/jm9006356
None	Unchecked	Km	44000.0	nM	10.1021/jm800134t
None	Unchecked	Km	311000.0	nM	10.1021/jm800134t
None	Unchecked	Ratio	0.0055	/s/microM	10.1021/jm800134t
None	Unchecked	Ratio	0.0061	/s/microM	10.1021/jm800134t
None	Unchecked	Ratio Ki	9.0	None	10.1021/jm9006356

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT001308	C#[O+].Cc1ncc(COP(=O)(O)OP(=O)(O)O)c(N)n1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1.O=CO>>Nc1cncn1[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O	MNXR162307
AKRT012352	CSCC[C@H](N)C(=O)O.Cc1ncc(COP(=O)(O)OP(=O)(O)O)c(N)n1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O	MNXR162307
AKRT014541	C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	MNXR137472
AKRT016637	N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O[C@H]4C[C@H](n5cnc6c(N)ncnc65)O[C@@H]4CO)[C@@H](O)[C@H]3O)c2[nH]1>>N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	None
AKRT016638	N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)O[C@H]4C[C@H](n5cnc6c(N)ncnc65)O[C@@H]4CO)[C@@H](O)[C@H]3O)c2[nH]1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	enzymemap_54446
AKRT021024	Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1.Nc1ncnc2[nH]cnc12>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	MNXR131621
AKRT021069	Nc1nc(=O)[nH]c2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	MNXR191588
AKRT021552	Nc1nc2c(ncn2[C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1.Nc1ncnc2[nH]cnc12>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	MNXR131626
AKRT021617	Nc1ncnc2[nH]cnc12.O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	R02557
AKRT021621	Nc1ncnc2[nH]cnc12.O=c1[nH]cnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	MNXR131047
AKRT021880	Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1	None
AKRT022215	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1nc(=O)[nH]c2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	RXN-15140
AKRT022216	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2[nH]cnc12	DEOXYADENPHOSPHOR-RXN
AKRT022217	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](C(=O)O)O1	enzymemap_7123
AKRT022218	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1	R02088
AKRT022219	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1	enzymemap_45159
AKRT022220	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](OP(=O)(O)O)[C@@H](CO)O1	enzymemap_45299
AKRT022221	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](OP(=O)(O)OP(=O)(O)O)[C@@H](CO)O1	enzymemap_45187
AKRT022222	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>O=CC[C@H](O)[C@H](O)CO	RXN-20660
AKRT022223	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>O=P(O)(O)O[C@@H]1C[C@H](O)[C@@H](CO)O1	DEOXYADENPHOSPHOR-RXN
AKRT022224	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>O=c1[nH]cnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	R02556
AKRT022225	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>OC[C@H]1O[C@@H](n2cnc3c(O)ncnc32)C[C@@H]1O	ADDALT-RXN
AKRT022230	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	R02088
AKRT022234	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	67652
AKRT022244	Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	67648
AKRT022250	Nc1ncnc2c1ncn2[C@H]1C[C@H](OP(=O)(O)O)[C@@H](CO)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1	RXN-14524