Rifamycin B
Basic information
- CAS
13929-35-6- Standard SMILES
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- InChIKey
SQTCRTQCPJICLD-KTQDUKAHSA-N- Molecular formula
- C39H49NO14
- Average molar mass
- 755.8 g/mol
- Monoisotopic mass
- 755.31530524
Overview
Rifamycin B is a member of rifamycins, a carboxylic acid, an organic heterotetracyclic compound and an acetate ester. It is a conjugate acid of a rifamycin B(2-).
Names & identifiers
- Preferred name
- Rifamycin B
- IUPAC
- 2-[[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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(29),2,4,9,19,21,25,27-octaen-27-yl]oxy]acetic acid
- English name
- 4-O-(Carboxymethyl)rifamycin
- Molecular formula
- C39H49NO14
- Molecular weight
- 755.8
Names & synonyms
RIFAMYCIN BNancimycin13929-35-64-O-(Carboxymethyl)rifamycin8DDB535DJICHEBI:17876DTXSID901037384NSC-145604Acetic acid, ((1,2-dihydro-5,6,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-9-yl)-oxy)-, 21-acetate2-(((7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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(29),2,4,9,19,21,25,27-octaen-27-yl)oxy)acetic acid2-[[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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(29),2,4,9,19,21,25,27-octaen-27-yl]oxy]acetic acidRefChem:179425
Show more names
C01848NCI-145-604Rifamycin impurity ARifaximin EP Impurity B
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 228 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 54
- Formal charge
- 0
- Complexity
- 1,460
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Ansamycins and related polyketides [PK05]
Physicochemical properties
- Melting point
- 300 ° · 300° (dec 160-164°)
- alpha
- 20 · D20 -11° (methanol)
- Boiling point
- 730.16 °C · 730.16°C (rough estimate)
- Density
- 1.2421 · 1.2421 (rough estimate)
- refractive index
- 1.535 · 1.5350 (estimate)
- solubility
- DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
- pka
- 2.69 · 2.69±0.10(Predicted)
- BRN
- 604953 · 604953
- Stability
- Unstable in solution
- FDA UNII
- 8 DDB535DJI · 8DDB535DJI
- Toxicity
- 50 in · LD50 in mice (mg/kg): 2040 i.v., >3000 i.p., s.c., and orally (Sensi, 1964)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Safety data
- Toxicity
- LD50 in mice (mg/kg): 2040 i.v., >3000 i.p., s.c., and orally (Sensi, 1964)
Chemistry & industry
Applications
UsesRifamycin B (Rifaximin EP Impurity B) is a Rifamycin (R508200) derivative as antibacterial agent.
UsesA Rifamycin (R508200) derivative as antibacterial agent.
Additional notes
DefinitionChEBI: Rifamycin B is a carboxylic acid, an acetate ester, an organic heterotetracyclic compound and a member of rifamycins. It is a conjugate acid of a rifamycin B(2-).
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Compound notes
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