Actinorhodin

Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor.^[1][2] The antibiotic effect of the substance was first noticed in 1947, when it was noted to inhibit the growth of S. aureus^[3]; with the full structure being described in 1966.^[4] The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic.^[5] The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change.^[6] It is a product of a Type II polyketide synthase biosynthetic pathway.^[7]

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Actinorhodin

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
CAS Number	1397-77-9 Y
3D model (JSmol)	Interactive image
Beilstein Reference	76401
ChEBI	CHEBI:2448 N
ChemSpider	16735642 Y
KEGG	C06691
PubChem CID	5280985
UNII	G4HH387T6Z Y
CompTox Dashboard (EPA)	DTXSID20930557
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 Y Key: VTIKDEXOEJDMJP-WYUUTHIRSA-N Y 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
SMILES 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
Chemical formula	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 YN ?) Infobox references

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