Molecule

rifamycin O

AlkaPlorer ID: AK004163

Synonym: 'NSC 182391', 'Rifamycin O', 'rifamycin O', 'Rifamycin, 4-O-(carboxymethyl)-1-deoxy-1,4-dihydro-4-hydroxy-1-oxo-, gamma-lactone'

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

Structure

SMILES: CO[C@H]1/C=C/O[C@@]2(C)OC3=C(C)C(O)=C4C(=O)C(=CC5(OCC(=O)O5)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/C39H47NO14/c1-17-11-10-12-18(2)37(48)40-24-15-39(51-16-26(42)53-39)29-27(33(24)46)32(45)22(6)35-28(29)36(47)38(8,54-35)50-14-13-25(49-9)19(3)34(52-23(7)41)21(5)31(44)20(4)30(17)43/h10-15,17,19-21,25,30-31,34,43-45H,16H2,1-9H3,(H,40,48)/b11-10+,14-13+,18-12-/t17-,19+,20+,21+,25-,30-,31+,34+,38-,39?/m0/s1

InChIKey: RAFHKEAPVIWLJC-KQOHHTLASA-N

Reference

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

PubChem CID: 5280468

CAS: 14487-05-9

LOTUS: LTS0004219

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Amycolatopsis mediterranei	Amycolatopsis	Pseudonocardiaceae	Pseudonocardiales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 753.7980000000003

TPSA？: 216.94

MolLogP？: 4.014120000000004

Number of H-Donors: 4

Number of H-Acceptors: 14

RingCount: 6

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT011290	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>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2(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)OCC(=O)O2	RXN-20245
AKRT011291	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(OCC(=O)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)C2(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)OCC(=O)O2	RIFAMYCIN-B-OXIDASE-RXN
AKRT011294	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2(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)OCC(=O)O2>>CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(OCC(=O)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	RXN-9612