Showing Metabocard for rifampicin (BASm0005019)

Common Name	Rifampicin
Description	A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)
Structure
Molecular Formula	C₄₃H₅₈N₄O₁₂
Average Mass	822.94020
Monoisotopic Mass	822.40512
IUPAC Name	(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-[(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-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
Traditional Name	(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-[(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-1,3,5(28),9,19,21,25(29),26
CAS Registry Number	13292-46-1
SMILES	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c([O-])c4c(O)c(c(/C=N/N5CC[NH+](C)CC5)c(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
InChI Identifier	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
InChI Key	JQXXHWHPUNPDRT-XHVADFQNSA-N
CHEBI ID	CHEBI:71365
HMDB ID	HMDB0015179
State	Solid
Water Solubility	4.13e-02 g/l
logP	3.85
logS	-4.30
pKa (Strongest Acidic)	6.90
pKa (Strongest Basic)	7.53
Hydrogen Acceptor Count	14
Hydrogen Donor Count	6
Polar Surface Area	220.15 Å²
Rotatable Bond Count	5
Physiological Charge	1
Formal Charge	0
Refractivity	225.58 m³·mol⁻¹
Polarizability	86.46

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