CAS 1397-77-9

Actinorhodin

Description:

Actinorhodin is a secondary metabolite produced by certain species of the bacterium Streptomyces, particularly Streptomyces coelicolor. It is a member of the anthracycline class of compounds and is characterized by its vibrant blue color, which is attributed to its unique chromophore structure. Actinorhodin exhibits antibiotic properties, making it significant in the field of microbiology and pharmacology. Its structure consists of a tetracyclic ring system with various functional groups that contribute to its biological activity. The compound is known for its ability to inhibit bacterial RNA synthesis, which underlies its effectiveness as an antibiotic. Additionally, actinorhodin has been studied for its potential applications in cancer therapy due to its cytotoxic effects on certain cancer cell lines. The compound is also of interest in research related to natural product biosynthesis and the genetic regulation of antibiotic production in microorganisms. Overall, actinorhodin represents an important example of the diverse chemical arsenal produced by soil-dwelling actinobacteria.

Formula: C₃₂H₂₆O₁₄

InChI: InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33-34,39-40H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1

InChI key: InChIKey=VTIKDEXOEJDMJP-WYUUTHIRSA-N

SMILES: O=C1C=2C(C(=O)C3=C1[C@@H](C)O[C@H](CC(O)=O)C3)=C(O)C=C(C2O)C=4C(O)=C5C(=C(O)C4)C(=O)C6=C(C5=O)[C@@H](C)O[C@H](CC(O)=O)C6

Synonyms:

• 1H-Naphtho[2,3-c]pyran, bimol. deriv.
• (1R,1′R,3S,3′S)-3,3′,4,4′,5,5′,10,10′-Octahydro-6,6′,9,9′-tetrahydroxy-1,1′-dimethyl-5,5′,10,10′-tetraoxo[8,8′-bi-1H-naphtho[2,3-c]pyran]-3,3′-diacetic acid
• [8,8′-Bi-1H-naphtho[2,3-c]pyran]-3,3′-diacetic acid, 3,3′,4,4′,5,5′,10,10′-octahydro-6,6′,9,9′-tetrahydroxy-1,1′-dimethyl-5,5′,10,10′-tetraoxo-, (1R,1′R,3S,3′S)-
• Actinorhodin
• Actinorhodin
• Actinorhodine
• [8,8′-Bi-1H-naphtho[2,3-c]pyran]-3,3′-diacetic acid, 3,3′,4,4′,5,5′,10,10′-octahydro-6,6′,9,9′-tetrahydroxy-1,1′-dimethyl-5,5′,10,10′-tetraoxo-, [1R-[1α,3β,8(1′R*,3′S*)]]-
• (8,8'-Bi-1H-naphtho(2,3-c)pyran)-3,3'-diacetic acid, 3,3',4,4',5,5',10,10'-octahydro-6,6',9,9'-tetrahydroxy-1,1'-dimethyl-5,5',10,10'-tetraoxo-, (1R,1'R,3S,3'S)-
• 2,2'-[(1R,1'R,3S,3'S)-5,5',10,10'-tetrahydroxy-1,1'-dimethyl-6,6',9,9'-tetraoxo-3,3',4,4',6,6',9,9'-octahydro-1H,1'H-8,8'-bibenzo[g]isochromene-3,3'-diyl]diacetic acid

Actinorhodin

CAS: 1397-77-9

Actinorhodin is a blue pigment and a redox-active microbial secondary metabolite. It is a potent, antibacterial, pH-responsive antibiotic (antibiotic) exhibiting antimicrobial activity against Gram-positive bacteria.

Formula: C₃₂H₂₆O₁₄

Color and Shape: Solid

Molecular weight: 634.54

Ref: TM-TN9061