sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate

• ChemBase ID: 132533
• Molecular Formular: C37H46NNaO12
• Molecular Mass: 719.75041
• Monoisotopic Mass: 719.2917702
• SMILES: Cc1c(c2c3c(cc(c2O)NC(=O)/C(=C\C=C/[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]([C@H](/C=C\O[C@@]2(C(=O)c3c1O2)C)OC)C)OC(=O)C)C)O)C)O)C)/C)[O-])O.[Na+]
• Canonical SMILES: CO[C@H]1/C=C\O[C@@]2(C)Oc3c(C2=O)c2c([O-])cc(c(c2c(c3C)O)O)NC(=O)/C(=C\C=C/[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C.[Na+]
• InChI: InChI=1S/C37H47NO12.Na/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;/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46);/q;+1/p-1/b11-10-,14-13-,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1
• InChIKey: YVOFSHPIJOYKSH-DITFEXNXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate
• IUPAC Traditional name: sodium (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-13-(acetyloxy)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^4,^7.0^5,^2^8]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-27-olate
• Synonyms: Rifamycin SV sodium salt; 利福霉素 SV 钠盐

Database IDs

• CAS Number: 14897-39-3
• EC Number: 238-965-7
• PubChem SID: 162226810
• PubChem CID: 71308574

CALCULATED PROPERTIES

• Acid pKa: 7.0917516
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): 4.1634398
• LogD (pH = 7.4): 3.6780498
• Log P: 4.1743436
• Molar Refractivity: 198.3485 cm^3
• Polarizability: 72.22435 Å^3
• Polar Surface Area: 204.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Potency: ≥900 units (dry basis)

DETAILS

Sigma Aldrich - R8626

Application
Rifamycin SV is a broad-spectrum semisynthetic antimicrobial agent of the rifamycin group. It is used to study potential genes, such as rif15 and rif16, which may be involved in the conversion of rifamycin SV into rifamycin B1. It is a potential treatment for traveler’s diarrhea (TD), Clostridium difficile-associated disease (CDAD) and rheumatoid knee synovitis2,3. It is used in electron spin resonance studies4.
Biochem/physiol Actions
Rifamycin SV inhibits selective (E. coli, B. subtilis) bacterial DNA-dependent RNA polymerase by binding to the polymerase β-subunit, a mechanism similar to rifabutin. It acts as a selective cytochrome P450 3A4 inducer. It has limited oral absorption that is active against Gram-positive bacteria and is moderately active against Gram-negative organisms2.