actinorhodin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477241707

| ImageFile = Actinorhodin.svg

| ImageSize = 250 px

| PIN = 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

| OtherNames =

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16735642

| 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

| InChIKey = VTIKDEXOEJDMJP-WYUUTHIRBL

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VTIKDEXOEJDMJP-WYUUTHIRSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 1397-77-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = G4HH387T6Z

| PubChem = 5280985

| KEGG = C06691

| Beilstein = 76401

| 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

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 2448

}}

|Section2={{Chembox Properties

| C=32 | H=26 | O=14

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor.{{cite journal |vauthors=Magnolo SK, Leenutaphong DL, DeModena JA |title=Actinorhodin production by Streptomyces coelicolor and growth of Streptomyces lividans are improved by the expression of a bacterial hemoglobin |journal=Bio/Technology |volume=9 |issue=5 |pages=473–6 |date=May 1991 |pmid=1367312 |doi= 10.1038/nbt0591-473|s2cid=21623645 |display-authors=etal}}{{cite journal |vauthors=Brian P, Riggle PJ, Santos RA, Champness WC |title=Global negative regulation of Streptomyces coelicolor antibiotic synthesis mediated by an absA-encoded putative signal transduction system |journal=J. Bacteriol. |volume=178 |issue=11 |pages=3221–31 |date=June 1996 |pmid=8655502 |pmc=178074 |doi= 10.1128/jb.178.11.3221-3231.1996}} The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic.{{cite journal|last=Tahlan|first=K|author2=Ahn SK|author3=Sing A|author4=Bodnaruk TD|author5=Willems AR|author6=Davidson AR|author7= Nodwell JR.|date=February 2007|title=Initiation of actinorhodin export in Streptomyces coelicolor|journal=Molecular Microbiology|volume=63|issue=4|pages=951–961|pmid=17338074|doi=10.1111/j.1365-2958.2006.05559.x|doi-access=free}} The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change.{{cite journal|last=Bystrykh|first=LV|author2=Fernández-Moreno MA|author3=Herrema JK|author4=Malpartida F|author5=Hopwood DA|author6= Dijkhuizen L|date=April 1996|title=Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)|journal=Journal of Bacteriology|volume=178|issue=8|pages=2238–44|doi=10.1128/jb.178.8.2238-2244.1996|pmid=8636024|pmc=177931}} It is a product of a Type II polyketide synthase biosynthetic pathway.{{cite journal | last=Javidpour | first=Pouya | last2=Bruegger | first2=Joel | last3=Srithahan | first3=Supawadee | last4=Korman | first4=Tyler P. | last5=Crump | first5=Matthew P. | last6=Crosby | first6=John | last7=Burkart | first7=Michael D. | last8=Tsai | first8=Shiou-Chuan | title=The Determinants of Activity and Specificity in Actinorhodin Type II Polyketide Ketoreductase | journal=Chemistry & Biology | volume=20 | issue=10 | date=2013 | pmid=24035284 | pmc=3855848 | doi=10.1016/j.chembiol.2013.07.016 | doi-access=free | pages=1225–1234}}