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13292-46-1 molecular structure
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(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate

ChemBase ID: 72799
Molecular Formular: C43H58N4O12
Molecular Mass: 822.94022
Monoisotopic Mass: 822.40512332
SMILES and InChIs

SMILES:
[C@@H]1([C@@H]([C@@H]([C@@H]([C@H](/C=C/O[C@]2(Oc3c(c(c4c(c(NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]1C)O)C)/C)c(c(c4c3C2=O)O)/C=N/N1CCN(CC1)C)O)O)C)C)OC)C)OC(=O)C)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-WLSIYKJHSA-N

Cite this record

CBID:72799 http://www.chembase.cn/molecule-72799.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl acetate
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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
IUPAC Traditional name
rifampicin
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,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
Synonyms
Rifadin
Rimactane
Rifampicin
Rifampin
Rifaldazine
Rifampicin
CAS Number
13292-46-1
PubChem SID
162037720
PubChem CID
5381226

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5381226 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

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Mechanism of Action
Inhibits DNA dependent RNA polymerase activity in susceptible cells expand Show data source
RNA polymerase inhibitor expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Prod. from Streptomyces mediterranei expand Show data source
Application(s)
Antibiotic expand Show data source
Antileprotic expand Show data source
Possesses antibacterial and antitubercular props. expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1764 external link
Research Area: Infection
Biological Activity:
Rifampin (Rifadin, Rimactane) is a bactericidal antibiotic agent of the rifamycin group. It is a semisynthetic compound derived from Amycolatopsis rifamycinica. RRifampicin is typically used to treat Mycobacterium infections, including tuberculosis and leprosy.With multidrug therapy used as the standard treatment of leprosy, Rifampin is always used in combination with dapsone and clofazimine to avoid eliciting agent resistance. [1]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Rifampicin
  • • Gadret, M. et al., Acta Cryst. B, 1975, 31, 1454, (cryst struct)
  • • Gallo, E.G. et al., Anal. Profiles Drug Subst., 1976, 5, 467, (rev, synth, anal)
  • • Girling, D.T. et al., J. Antimicrob. Chemother., 1977, 3, 115, (tox, rev)
  • • IARC Monog., 1980, 24, 243; Suppl. 7, 71, (rev)
  • • Sensi, P., Chron. Drug Discovery, 1982, 1, 201, (rev)
  • • Sensi, P., Rev. Infect. Dis., (Suppl. 3), 1983, 5, 402, (rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 8227, (synonyms)
  • • Taguchi, M. et al., Chem. Pharm. Bull., 1988, 36, 4157, (pmr, cmr)
  • • Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 937
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 197
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RKP000
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PATENTS

PATENTS

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INTERNET

INTERNET

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