[(9Z,19Z,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
Basic information
- CAS
13553-79-2- Standard SMILES
COC1/C=C\OC2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C/C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C)C4=O- InChIKey
BTVYFIMKUHNOBZ-QXMMDKDBSA-N- Molecular formula
- C37H45NO12
- Average molar mass
- 695.8 g/mol
- Monoisotopic mass
- 695.29417587
Names & identifiers
- Preferred name
- [(9Z,19Z,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
- IUPAC
- [(9Z,19Z,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
- English name
- Rifamycin S
- Molecular formula
- C37H45NO12
- Molecular weight
- 695.75
Names & synonyms
Rafamycin SC37H45NO12[(9Z,19Z,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] acetateNSC144130(12Z,14E,24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate (7CI,8CI)Rifamycin,4-dideoxy-1,4-dihydro-1,4-dioxo-2,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, -5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate2,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetateWLN: T C6 B65-24- A D E 2BC G& AV DV GV LO NO F&VM OU B&U D&U MHT&&TJ IQ J1 M1 QO1 R1 SOV1 T1 UQ V1
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 195 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 3
- Heavy atoms
- 50
- Formal charge
- 0
- Complexity
- 1,480
Experimental & physicochemical properties
LogP0.7
Physicochemical properties
- Melting point
- 179 · 179-181°C (dec.)
- alpha
- 20 · D20 +476° (c = 0.1 in methanol)
- Boiling point
- 700.89 °C · 700.89°C (rough estimate)
- Density
- 1.2387 · 1.2387 (rough estimate)
- refractive index
- 1.663 · 1.6630 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 3.85 · 3.85±0.70(Predicted)
- color
- Orange to Dark Orange
- λmax
- 390 nm · 390nm(MeOH)(lit.)
- Merck
- 14 · 14,8217
- InChIKey
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- rtecs
- KD1925000
- hs_code
- 2941.90.1050
- Toxicity
- LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- target organs
- Kidney
- Hazard statements
- H371
- REACH Registrations
- Active
- Hazard Classifications
- STOT RE 2 Oral
- Precautionary statements
- P501-P260-P270-P264-P308+P311-P405
Chemistry & industry
Applications
UsesRifamycin S (Rifaximin EP Impurity E) is a semi-synthetic antibiotic.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Rifamycin S is an organic molecular entity.
Suppliers
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Compound notes
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