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5'-deoxyadenosine

AlkaPlorer ID: AK019904

Synonym: "5'-DEOXYADENOSINE", "5'-deoxyadenosine", "5'-Deoxyadenosine"

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

Structure

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

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InChI: InChI=1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

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InChIKey: XGYIMTFOTBMPFP-KQYNXXCUSA-N

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Reference

PubChem CID: 439182

CAS: 4754-39-6

LOTUS: LTS0011251

NPASS: NPC317821

Properties Information

Molecule Weight: 251.246

TPSA？: 119.31000000000002

MolLogP？: -0.9524

Number of H-Donors: 3

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Chlorocebus sabaeus Vero MIC 2.0 ug.mL-1 10.1021/jm960770e
Chlorocebus sabaeus Vero MIC 7.0 ug.mL-1 10.1021/jm960770e
Chlorocebus sabaeus Vero MIC 400.0 ug.mL-1 10.1021/jm960770e
Homo sapiens Heat shock cognate 71 kDa protein Kd 130000.0 nM 10.1021/acs.jmedchem.5b02001
Homo sapiens Heat shock cognate 71 kDa protein Kd 131825.67 nM 10.1021/acs.jmedchem.5b02001
Homo sapiens HeLa MIC 0.1 ug.mL-1 10.1021/jm960770e
Homo sapiens HeLa MIC 400.0 ug.mL-1 10.1021/jm960770e
Homo sapiens S-methyl-5-thioadenosine phosphorylase K cat 4.8 1/sec 10.1016/j.bmcl.2005.03.107
Homo sapiens S-methyl-5-thioadenosine phosphorylase Km 6000.0 nM 10.1016/j.bmcl.2005.03.107
Homo sapiens S-methyl-5-thioadenosine phosphorylase Ratio 0.8 1/uM*sec 10.1016/j.bmcl.2005.03.107
Rattus norvegicus Adenosine A1 receptor Ki 269.0 nM 10.1021/jm00007a014
Rattus norvegicus Adenosine A1 receptor Ki 1820.0 nM 10.1021/jm00020a014
Rattus norvegicus Adenosine A1 receptor Ki 12100.0 nM 10.1021/jm00020a014
Rattus norvegicus Adenosine A2a receptor Ki 596.0 nM 10.1021/jm00007a014
Rattus norvegicus Adenosine A3 receptor Ki 2830.0 nM 10.1021/jm00007a014
Rattus norvegicus Rattus norvegicus GTP shift 6.6 None 10.1021/jm00020a014

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT006965 CC1=C(CCC(=O)O)C2=N/C1=C\c1c(C)c(CCC(=O)O)c3n1[Fe]n1/c(c(C)c(CCC(=O)O)/c1=C/2)=C\C1=N/C(=C\3)C(C)=C1CCC(=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>>C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O R12002
AKRT012348 CSCC[C@H](N)C(=O)O.C[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 R12162
AKRT012349 CSCC[C@H](N)C(=O)O.C[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 MNXR101090
AKRT014069 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@@H](O)[C@@H](O)[C@@H](O)C=O MNXR192383
AKRT014070 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1OC(O)[C@H](O)[C@@H]1O RXN0-6550
AKRT014071 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1O[C@@H](O)C(O)[C@@H]1O MNXR152703
AKRT014072 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1O[C@@H](n2cnc3c(=O)[nH]cnc32)[C@H](O)[C@@H]1O RXN-15568
AKRT014073 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1O[C@H](OP(=O)(O)O)[C@H](O)[C@@H]1O RXN-14304
AKRT014074 C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>Nc1ncnc2[nH]cnc12 RXN-14304
AKRT014512 C[S+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O R01078
AKRT014527 C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.Cc1c2[nH]c(c1CCC(=O)O)Cc1[nH]c(c(CCC(=O)O)c1C)Cc1[nH]c(c(CCC(=O)O)c1C)Cc1[nH]c(c(C)c1CCC(=O)O)C2>>C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O HEMN-RXN
AKRT014533 C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O RXN-8799