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NADH(2-)

AlkaPlorer ID: AK011476

Synonym: '1,4-DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE', 'NADH dianion', 'NADH', 'Reduced nicotinamide adenine dinucleotide', 'Dihydronicotinamide adenine dinucleotide', 'nicotinamide adenine dinucleotide (reduced)', 'DPNH'

IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate

Structure

SMILES: N=C(O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](N4C=NC5=C(N)N=CN=C54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1

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InChI: InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

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InChIKey: BOPGDPNILDQYTO-NNYOXOHSSA-N

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Properties Information

Molecule Weight: 665.4460000000005

TPSA？: 318.61000000000007

MolLogP？: -1.6364299999999978

Number of H-Donors: 9

Number of H-Acceptors: 18

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Escherichia coli K-12 Enoyl-[acyl-carrier-protein] reductase Kcat 10.8 /s 10.1016/j.bmcl.2020.127651
Escherichia coli K-12 Enoyl-[acyl-carrier-protein] reductase Kcat/Km 0.15 microM/s 10.1016/j.bmcl.2020.127651
Escherichia coli K-12 Enoyl-[acyl-carrier-protein] reductase Km 70200.0 nM 10.1016/j.bmcl.2020.127651
Homo sapiens Histone deacetylase 6 Inhibition -5.88 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 4.98 % 10.6019/CHEMBL4808148
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.98 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.01 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 6.97 % 10.21203/rs.3.rs-23951/v1
None Unchecked Kcat 0.16 /s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat 0.38 /s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat 3.44 /s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat 3.65 /s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat/Km 0.004 microM/s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat/Km 0.009 microM/s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat/Km 0.07 microM/s 10.1016/j.bmcl.2020.127651
None Unchecked Kcat/Km 0.11 microM/s 10.1016/j.bmcl.2020.127651
None Unchecked Km 30900.0 nM 10.1016/j.bmcl.2020.127651
None Unchecked Km 41700.0 nM 10.1016/j.bmcl.2020.127651
None Unchecked Km 44200.0 nM 10.1016/j.bmcl.2020.127651
None Unchecked Km 51500.0 nM 10.1016/j.bmcl.2020.127651

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT016778 NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=CC1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1 enzymemap_48398
AKRT016779 NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1.O=Cc1ccncc1>>NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1C(=O)c1ccncc1 RXN-18722
AKRT016780 NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1>>NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=CC1 MNXR130677
AKRT016781 NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O RXN0-4401
AKRT016782 NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O MNXR130677