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Xiamycin

AlkaPlorer ID: AK023076

Synonym: None

IUPAC Name: (16R,17S,18S,21S)-18-hydroxy-17,21-dimethyl-10-azapentacyclo[11.8.0.03,11.04,9.016,21]henicosa-1,3(11),4,6,8,12-hexaene-17-carboxylic acid

Structure

SMILES: C[C@@]1(C(=O)O)[C@@H](O)CC[C@]2(C)C3=CC4=C(C=C3CC[C@@H]12)NC1=CC=CC=C14

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InChI: InChI=1S/C23H25NO3/c1-22-10-9-20(25)23(2,21(26)27)19(22)8-7-13-11-18-15(12-16(13)22)14-5-3-4-6-17(14)24-18/h3-6,11-12,19-20,24-25H,7-10H2,1-2H3,(H,26,27)/t19-,20+,22-,23+/m1/s1

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InChIKey: XUTJPVCJXVRRLB-SKWRMQMOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Streptomyces olivaceus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 363.4570000000001

TPSA？: 73.32

MolLogP？: 4.386800000000004

Number of H-Donors: 3

Number of H-Acceptors: 2

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis IZ 13.5 mm 10.1016/j.bmcl.2010.09.010
Candida albicans Candida albicans Activity nan None 10.1016/j.bmcl.2010.09.010
Chlorocebus sabaeus Vero CC50 138120.0 nM 10.1021/acs.jnatprod.5b00634
Enterococcus faecalis Enterococcus faecalis IZ 12.0 mm 10.1016/j.bmcl.2010.09.010
Escherichia coli Escherichia coli Activity nan None 10.1016/j.bmcl.2010.09.010
Homo sapiens CWR22R IC50 30000.0 nM 10.1016/j.bmcl.2010.09.010
Homo sapiens HeLa CC50 44.3 ug.mL-1 10.1016/j.bmcl.2010.09.010
Homo sapiens HT-29 IC50 30000.0 nM 10.1016/j.bmcl.2010.09.010
Homo sapiens K562 GI50 36.7 ug.mL-1 10.1016/j.bmcl.2010.09.010
Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition nan % 10.1016/j.bmcl.2010.09.010
Mus musculus L929 GI50 49.8 ug.mL-1 10.1016/j.bmcl.2010.09.010
Mycolicibacterium vaccae Mycolicibacterium vaccae IZ 14.0 mm 10.1016/j.bmcl.2010.09.010
Penicillium chrysogenum Penicillium chrysogenum Activity nan None 10.1016/j.bmcl.2010.09.010
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity nan None 10.1016/j.bmcl.2010.09.010
Pseudomonas aeruginosa Pseudomonas aeruginosa IZ 15.0 mm 10.1016/j.bmcl.2010.09.010
Sporobolomyces salmonicolor Sporobolomyces salmonicolor Activity nan None 10.1016/j.bmcl.2010.09.010
Staphylococcus aureus Staphylococcus aureus IZ 14.0 mm 10.1016/j.bmcl.2010.09.010
Staphylococcus aureus Staphylococcus aureus IZ 15.0 mm 10.1016/j.bmcl.2010.09.010
None NON-PROTEIN TARGET EC50 20140.0 nM 10.1021/acs.jnatprod.5b00634
None NON-PROTEIN TARGET IC50 29990.0 nM 10.1016/j.bmcl.2010.09.010
None NON-PROTEIN TARGET IC50 30000.0 nM 10.1016/j.bmcl.2010.09.010
None Unchecked Ratio CC50/EC50 7.0 None 10.1021/acs.jnatprod.5b00634

Metabolism Information