Molecule

rifamycin S

AlkaPlorer ID: AK003878

Synonym: None

IUPAC Name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate

Structure

SMILES: CO[C@H]1/C=C/O[C@@]2(C)OC3=C(C)C(O)=C4C(=O)C(=CC(=O)C4=C3C2=O)N=C(O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C

InChI: InChI=1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N

Reference

Biosynthetic origins of the oxygen atoms in the ansamycin antibiotics rifamycin B, O, and S

PubChem CID: 6436726

CAS: 13553-79-2

LOTUS: LTS0256211

NPASS: NPC485812

Source

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

Properties Information

Molecule Weight: 695.7620000000003

TPSA？: 198.48

MolLogP？: 4.470620000000005

Number of H-Donors: 4

Number of H-Acceptors: 12

RingCount: 5

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Enterococcus faecalis	Enterococcus faecalis	MIC	16.0	ug.mL-1	10.1021/np050272l
Escherichia coli	Escherichia coli	MIC	128.0	ug.mL-1	10.1021/np050272l
Escherichia coli	Escherichia coli	MIC90	780.0	nM	10.1016/j.bmcl.2011.08.054
Escherichia coli	Escherichia coli	MIC90	100000.0	nM	10.1016/j.bmcl.2011.08.054
Haemophilus influenzae	Haemophilus influenzae	MIC	0.01	ug.mL-1	10.1021/np050272l
Mycobacterium tuberculosis	DNA-directed RNA polymerase beta chain	IC50	10.0	nM	10.1016/j.bmcl.2011.08.054
Mycobacterium tuberculosis	DNA-directed RNA polymerase beta chain	logIC50	-2.173	None	10.1016/j.bmcl.2011.08.054
Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	30.0	nM	10.1016/j.bmcl.2011.08.054
Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	400.0	nM	10.1016/j.bmcl.2011.08.054
Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	0.1	ug.mL-1	10.1021/np050272l
Staphylococcus aureus	Staphylococcus aureus	MIC	0.01	ug.mL-1	10.1021/np050272l
Staphylococcus aureus	Staphylococcus aureus	MIC	0.016	ug.mL-1	10.1016/j.bmcl.2007.08.048
Staphylococcus aureus	Staphylococcus aureus	MIC	4.0	ug.mL-1	10.1016/j.bmcl.2007.08.048
Staphylococcus aureus	Staphylococcus aureus	MIC	64.0	ug.mL-1	10.1016/j.bmcl.2007.08.048
Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	0.1	ug.mL-1	10.1021/np050272l
None	Unchecked	IC50	36000.0	nM	10.1016/j.bmcl.2011.08.054
None	Unchecked	logIC50	1.557	None	10.1016/j.bmcl.2011.08.054

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011288	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O	RXN-20243
AKRT011292	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O.O=C(CO)[C@@H](O)[C@H](O)COP(=O)(O)O>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(OC(=O)CO)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C	RXN-20244
AKRT011293	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C	R06999