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2'-deoxyadenosine 5'-monophosphate(2-)

AlkaPlorer ID: AK003818

Synonym: "deoxy-5'-adenylic acid", 'Deoxyadenosine monophosphate', "2'-deoxyadenosine 5'-monophosphate", "2'-Deoxyadenosine 5'-phosphate", "2'-deoxy-5'-adenosine monophosphate", "deoxyadenosine 5'-monophosphate", 'dAMP(2-)', "2'-Deoxyadenosine 5'-monophosphate", "deoxyadenosine 5'-phosphate", 'dAMP', 'deoxy-AMP', "2'-deoxyadenylic acid", "2'-deoxyadenosine 5'-(dihydrogen phosphate)", "2'-deoxy-AMP", "2'-DEOXYADENOSINE-5'-MONOPHOSPHATE", "2'-dAMP", 'Deoxyadenylic acid', "2'-deoxyadenosine monophosphate"

IUPAC Name: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate

Structure

SMILES: NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](COP(=O)(O)O)O3)C2=NC=N1

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InChI: InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

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InChIKey: KHWCHTKSEGGWEX-RRKCRQDMSA-N

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Reference

PubChem CID: 12599

CAS: 25191-20-2

LOTUS: LTS0155783

SuperNatural Ⅲ: SN0186047-02

NPASS: NPC323828

Properties Information

Molecule Weight: 331.225

TPSA？: 165.83999999999995

MolLogP？: -0.8338000000000001

Number of H-Donors: 4

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli K-12 Beta-lactamase AmpC Potency 562.3 nM None
Homo sapiens Adenylate kinase 1 Kcat 240.0 /s 10.1016/j.bmcl.2014.07.036
Homo sapiens Adenylate kinase 1 Kcat/Km 0.16 10'6/M/s 10.1016/j.bmcl.2014.07.036
Homo sapiens Adenylate kinase 1 Km 1500000.0 nM 10.1016/j.bmcl.2014.07.036
Homo sapiens Adenylate kinase 2 Kcat 110.0 /s 10.1016/j.bmcl.2014.07.036
Homo sapiens Adenylate kinase 2 Kcat/Km 0.5 10'6/M/s 10.1016/j.bmcl.2014.07.036
Homo sapiens Adenylate kinase 2 Km 210000.0 nM 10.1016/j.bmcl.2014.07.036
Homo sapiens Alpha-synuclein Potency 14125.4 nM None
Homo sapiens Chromobox protein homolog 1 Potency 44668.4 nM None
Homo sapiens DNA polymerase iota Potency 14125.4 nM None
Homo sapiens Geminin Potency 25929.0 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 10322.5 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 79432.8 nM None
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 25929.0 nM None
Homo sapiens Runt-related transcription factor 1/Core-binding factor subunit beta Potency 31622.8 nM None
Homo sapiens Sphingomyelin phosphodiesterase Potency 31622.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 2310.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 3264.3 nM None
None Unchecked Activity nan None 10.1021/acs.jmedchem.0c01747

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT015549 Cn1cnc2c(ncn2[C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c1=N>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1 RXN-18739
AKRT016495 N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]3O)c2[nH]1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1 None
AKRT021389 Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1 None
AKRT021881 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](COP(=O)(O)O)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)OP(=O)(O)O)O1 None
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
AKRT022226 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1.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](COP(=O)(O)OP(=O)(O)O)O1.Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1 None
AKRT022227 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1.O=P(O)(O)OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]1O>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1.O=P(O)(O)OC[C@H]1OC(O)[C@H](O)[C@@H]1O None
AKRT022228 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2[nH]cnc12 57824
AKRT022229 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@@H]2OP(=O)(O)OC[C@H]2O1 MNXR136084
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
AKRT022231 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O1 DEOXYADENYLATE-KINASE-RXN
AKRT022232 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O1 MNXR152578
AKRT022233 Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>O=P(O)(O)OC[C@H]1OC(O)C[C@@H]1O 57824
AKRT022235 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](COP(=O)(O)O)O1 R01547
AKRT022245 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](COP(=O)(O)O)O1 RXN-14195
AKRT022251 Nc1ncnc2c1ncn2[C@H]1C[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1 enzymemap_56892
AKRT022720 O=C(O)CC(Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)C(=O)O>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1 enzymemap_85781
AKRT024212 O=c1[nH]cnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1>>Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1 MNXR131036