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Lactoquinomycin

AlkaPlorer ID: AK015434

Synonym: None

IUPAC Name: (11R,15R,17R)-5-[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione

Structure

SMILES: C[C@H]1O[C@@H]2CC(=O)O[C@@H]2C2=C1C(=O)C1=C(C=CC([C@H]3C[C@@H](N(C)C)[C@H](O)[C@@H](C)O3)=C1O)C2=O

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InChI: InChI=1S/C24H27NO8/c1-9-17-19(24-15(31-9)8-16(26)33-24)22(29)12-6-5-11(21(28)18(12)23(17)30)14-7-13(25(3)4)20(27)10(2)32-14/h5-6,9-10,13-15,20,24,27-28H,7-8H2,1-4H3/t9-,10-,13-,14-,15-,20-,24+/m1/s1

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InChIKey: NYJGMJFBEVSQNN-CNRHASOASA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 457.4790000000002

TPSA？: 122.60000000000002

MolLogP？: 1.3116

Number of H-Donors: 2

Number of H-Acceptors: 9

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Candida albicans Candida albicans MIC 5.0 ug.mL-1 10.1021/acs.jnatprod.8b00544
Escherichia coli Escherichia coli MIC 2.0 ug.mL-1 10.1021/acs.jnatprod.8b00544
Homo sapiens cAMP-dependent protein kinase alpha-catalytic subunit Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Cyclin-dependent kinase 1/cyclin B1 Inhibition 2.0 % 10.1021/jm900075g
Homo sapiens Cyclin-dependent kinase 2 Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Dual specificity mitogen-activated protein kinase kinase 1 Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Ephrin type-A receptor 1 Inhibition 8.0 % 10.1021/jm900075g
Homo sapiens Epidermal growth factor receptor erbB1 Inhibition 26.0 % 10.1021/jm900075g
Homo sapiens Fibroblast growth factor receptor 1 Inhibition 38.0 % 10.1021/jm900075g
Homo sapiens Focal adhesion kinase 1 Inhibition 12.0 % 10.1021/jm900075g
Homo sapiens HCT-116 IC50 43.0 nM 10.1021/acs.jnatprod.8b00544
Homo sapiens Hepatocyte growth factor receptor Inhibition 14.0 % 10.1021/jm900075g
Homo sapiens Inhibitor of nuclear factor kappa B kinase beta subunit Inhibition 41.0 % 10.1021/jm900075g
Homo sapiens Insulin-like growth factor I receptor Inhibition 2.0 % 10.1021/jm900075g
Homo sapiens Insulin receptor Inhibition 1.0 % 10.1021/jm900075g
Homo sapiens Macrophage colony stimulating factor receptor Inhibition 6.0 % 10.1021/jm900075g
Homo sapiens MAP kinase ERK1 Inhibition 7.0 % 10.1021/jm900075g
Homo sapiens MAP kinase ERK2 Inhibition 6.0 % 10.1021/jm900075g
Homo sapiens MAP kinase p38 alpha Inhibition 49.0 % 10.1021/jm900075g
Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 5 Inhibition 34.0 % 10.1021/jm900075g
Homo sapiens Nerve growth factor receptor Trk-A Inhibition 14.0 % 10.1021/jm900075g
Homo sapiens PC-3 IC50 15.0 nM 10.1021/acs.jnatprod.8b00544
Homo sapiens Platelet-derived growth factor receptor alpha Inhibition 15.0 % 10.1021/jm900075g
Homo sapiens Platelet-derived growth factor receptor beta Inhibition 32.0 % 10.1021/jm900075g
Homo sapiens Protein kinase C alpha Inhibition 16.0 % 10.1021/jm900075g
Homo sapiens Protein kinase C theta Inhibition 22.0 % 10.1021/jm900075g
Homo sapiens Pyruvate dehydrogenase kinase isoform 1 Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Receptor protein-tyrosine kinase erbB-4 Inhibition 5.0 % 10.1021/jm900075g
Homo sapiens Rho-associated protein kinase 1 Inhibition 1.0 % 10.1021/jm900075g
Homo sapiens Rho-associated protein kinase 2 IC50 11.0 nM 10.1021/acs.jnatprod.8b00544
Homo sapiens Ribosomal protein S6 kinase 1 Inhibition 16.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT Activity nan None 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT IC50 149.0 nM 10.1016/j.bmcl.2013.11.020
Homo sapiens Serine/threonine-protein kinase AKT IC50 149.0 nM 10.1021/jm3003203
Homo sapiens Serine/threonine-protein kinase AKT IC50 149.0 nM 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT IC50 30400.0 nM 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT IC50 38500.0 nM 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT Inhibition 92.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase AKT2 Inhibition 99.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase Aurora-A Inhibition 17.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase Chk1 Inhibition 10.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase NEK2 Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase PLK1 Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Serine/threonine-protein kinase Sgk1 Inhibition 20.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase ABL Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase BTK Inhibition 1.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase CSK Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase FYN Inhibition 17.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase LCK Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase Lyn Inhibition 3.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase receptor FLT3 Inhibition 4.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase SRC Inhibition 0.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase SYK Inhibition 2.0 % 10.1021/jm900075g
Homo sapiens Tyrosine-protein kinase YES Inhibition 14.0 % 10.1021/jm900075g
Homo sapiens Vascular endothelial growth factor receptor 1 Inhibition 29.0 % 10.1021/jm900075g
Homo sapiens Vascular endothelial growth factor receptor 2 Inhibition 21.0 % 10.1021/jm900075g
Staphylococcus aureus Staphylococcus aureus MIC 0.25 ug.mL-1 10.1021/acs.jnatprod.8b00544
None NON-PROTEIN TARGET IC50 50.0 nM 10.1021/jm900075g

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014068 C[C@H]1O[C@@H](c2ccc3c(c2O)C(=O)C2=C(C3=O)[C@H]3OC(=O)C[C@H]3O[C@@H]2C)C[C@@H](N(C)C)[C@@H]1O>>C[C@H]1OC(C2=CC(=O)c3c(O)c4c(c(O)c3C2=O)[C@@H](C)O[C@@H]2CC(=O)O[C@H]42)CC(N(C)C)[C@@H]1O RXN-18117