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13292-46-1 molecular structure
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(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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-13-yl acetate

ChemBase ID: 134128
Molecular Formular: C43H58N4O12
Molecular Mass: 822.94022
Monoisotopic Mass: 822.40512332
SMILES and InChIs

SMILES:
Cc1c(c2c3c4c1O[C@@](C4=O)(O/C=C\[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]([C@H](/C=C\C=C(/C(=O)Nc(c2O)c(c3O)/C=N/N1CCN(CC1)C)\C)C)O)C)O)C)OC(=O)C)C)OC)C)O
Canonical SMILES:
CO[C@H]1/C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(/C=N/N4CCN(CC4)C)c(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
InChI:
InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11-,19-14-,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
InChIKey:
JQXXHWHPUNPDRT-YOPQJBRCSA-N

Cite this record

CBID:134128 http://www.chembase.cn/molecule-134128.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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-13-yl acetate
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
IUPAC Traditional name
(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-N-(4-methylpiperazin-1-yl)carboximidoyl]-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-13-yl acetate
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[N-(4-methylpiperazin-1-yl)carboximidoyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
Synonyms
Rifampicin
3-(4-Methylpiperazinyliminomethyl)rifamycin SV
Rifampin
Rifamycin AMP
3-(4-甲基-1-哌嗪基亚胺甲基)利福霉素SV
利米定
甲哌利福霉素
利福平
CAS Number
13292-46-1
EC Number
236-312-0
MDL Number
MFCD00151389
Beilstein Number
5723476
PubChem SID
24899363
162228405
24899383
24888155
24899391
24870383
PubChem CID
24871024

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 24871024 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 6.8984513  H Acceptors 14 
H Donor LogD (pH = 5.5) 1.6852435 
LogD (pH = 7.4) 2.7622907  Log P 2.7698967 
Molar Refractivity 225.5828 cm3 Polarizability 86.47999 Å3
Polar Surface Area 220.15 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: soluble100 mg/mL expand Show data source
H2O: soluble1.3 mg/mL (pH 4.3) expand Show data source
H2O: soluble2.5 mg/mL at 25 °C (pH 7.3) expand Show data source
Apperance
crystalline expand Show data source
faint-orange to red-brown powder expand Show data source
powder expand Show data source
RTECS
VJ7000000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
≥97% (HPLC) expand Show data source
≥97.0% (HPLC) expand Show data source
Grade
Biotechnology Performance Certified expand Show data source
VETRANAL™, analytical standard expand Show data source
Suitability
plant cell culture tested expand Show data source
Impurities
endotoxin, tested expand Show data source
Sterility
γ-irradiated expand Show data source
Empirical Formula (Hill Notation)
C43H58N4O12 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - R5777 external link
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - R7382 external link
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Application
Rifampicin, a rifamycin, is active against mycobacteria. Rifamycin, is also an inhibitor of chloroplast RNA polymerase and may be used to study chloroplast-level DNA transcription in plants.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - R3501 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Rifampicin inhibits the assembly of DNA and protein into mature virus particles. It inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase, which results in cell death1.
Application
Rifampicin is used to treat Tuberculosis and Tuberculosis-related mycobacterial infections1. It is widely used as an antipruritic agent in the autoimmune cholestatic liver disease, primary biliary cirrhosis (PBC). It has been shown to cause hepatitis2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - R8883 external link
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Reconstitution
在小瓶中直接用甲醇制备储存液 (25mg/mL)。
Application
Rifampicin is used as an inhibitor of transcription initiation, blocking initiation of RNA synthesis.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 83907 external link
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Application
Rifampicin is used as a selective cytochrome P4503A4 inducer. Studies have shown that rifampicin inhibits African Swine Fever Virus replication in tissue culture 1 and inhibits the induction of tyrosine aminotransferase by cortisol in rat hepatoma cells grown in culture 2.
Sigma Aldrich - 46713 external link
Biochem/physiol Actions
Inhibits the assembly of DNA and protein into mature virus particles.
Mode of Action: Inhibits initiation of RNA synthesis by binding to β-subunit of RNA polymerase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

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PATENTS

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