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Antibiotic
Actinorhodin
Другие языки:

Actinorhodin

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Actinorhodin
Actinorhodin.svg
Names
Preferred IUPAC name
2,2′-[(1R,1′R,3S,3′S)-5,5′,10,10′-Tetrahydroxy-6,6′,9,9′-tetraoxo-3,3′,4,4′,6,6′,9,9′-octahydro-1H,1′H-[8,8′-binaphtho[2,3-c]pyran]-3,3′-diyl]diacetic acid
Identifiers
3D model (JSmol)
76401
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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 checkY
    Key: VTIKDEXOEJDMJP-WYUUTHIRSA-N checkY
  • InChI=1/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
    Key: VTIKDEXOEJDMJP-WYUUTHIRBL
  • OC(=O)C[C@@H]5CC=6C(=O)c4c(O)cc(c3cc(O)c2C(=O)C=1C[C@@H](CC(O)=O)O[C@H](C)C=1C(=O)c2c3O)c(O)c4C(=O)C=6[C@@H](C)O5
Properties
C32H26O14
Molar mass 634.546 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor. The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic. The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change.


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