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MetaCyc Compound: 4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate

Synonyms: bicyclic intermediate, intermediate4

Superclasses: a secondary metabolite

This intermediate is formed by an ActIV-catalyzed intramolecular aldol condensation of a (3'-hydroxy-2'-(3''-oxobutanoyl)phenyl)-3,5-dioxohexanethioate-[PKS-acp].

Dr. Martin Rejzek of the Department of Biological Chemistry at the John Innes Centre used the ChemDraw Ultra software to determine the IUPAC name of this compound.

Citations: [Ichinose99, CambridgeSoft06, BookerMilburn05, Taguchi04 , Taguchi07, FernandezMoreno94, Taguchi00, Tahlan07]

Chemical Formula: C16H13O6

Molecular Weight: 301.28 Daltons

Monoisotopic Molecular Weight: 302.079038182 Daltons

4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate compound structure

SMILES: CC(C1(=C(CC2(=CC=CC(=C(C1=O)2)O))CC(=O)CC(=O)[O-]))=O

InChI: InChI=1S/C16H14O6/c1-8(17)14-10(6-11(18)7-13(20)21)5-9-3-2-4-12(19)15(9)16(14)22/h2-4,19H,5-7H2,1H3,(H,20,21)/p-1


Unification Links: PubChem:25245554

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -43.33751Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

actinorhodin biosynthesis :
4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate + NADPH + H+ → (S)-4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-hydroxybutanoate + NADP+

Reactions known to produce the compound:

actinorhodin biosynthesis :
4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate-[PKS-acp] + H2O → 4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate + polyketide synthase + H+


BookerMilburn05: Booker-Milburn KI, Gillan R, Kimberley M, Taguchi T, Ichinose K, Stephenson GR, Ebizuka Y, Hopwood DA (2005). "Enantioselective reduction of beta-keto acids with engineered Streptomyces coelicolor." Angew Chem Int Ed Engl 44(7);1121-5. PMID: 15645472

CambridgeSoft06: CambridgeSoft (2006). "ChemDraw Ultra 10.0." ChemDraw, Level Ultra, Version 10.0.

FernandezMoreno94: Fernandez-Moreno MA, Martinez E, Caballero JL, Ichinose K, Hopwood DA, Malpartida F (1994). "DNA sequence and functions of the actVI region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor A3(2)." J Biol Chem 269(40);24854-63. PMID: 7929165

Ichinose99: Ichinose K, Surti C, Taguchi T, Malpartida F, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Hopwood DA (1999). "Proof that the ACTVI genetic region of Streptomyces coelicolor A3(2) is involved in stereospecific pyran ring formation in the biosynthesis of actinorhodin." Bioorg Med Chem Lett 9(3);395-400. PMID: 10091691

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Taguchi00: Taguchi T, Itou K, Ebizuka Y, Malpartida F, Hopwood DA, Surti CM, Booker-Milburn KI, Stephenson GR, Ichinose K (2000). "Chemical characterisation of disruptants of the Streptomyces coelicolor A3(2) actVI genes involved in actinorhodin biosynthesis." J Antibiot (Tokyo) 53(2);144-52. PMID: 10805574

Taguchi04: Taguchi T, Kunieda K, Takeda-Shitaka M, Takaya D, Kawano N, Kimberley MR, Booker-Milburn KI, Stephenson GR, Umeyama H, Ebizuka Y, Ichinose K (2004). "Remarkably different structures and reaction mechanisms of ketoreductases for the opposite stereochemical control in the biosynthesis of BIQ antibiotics." Bioorg Med Chem 12(22);5917-27. PMID: 15498668

Taguchi07: Taguchi, T., et al. (2007). "Possible Involvement of ActVI-ORFA in Transcriptional Regulation of actVI Tailoring-StepGenes for Actinorhodin Biosynthesis." FEMS Microbiol. Lett., Online Early.

Tahlan07: Tahlan, K., et al (2007). "Initiation of Actinorhodin export in Streptomyces coelicolor." Molecular Microbiology, OnlineEarly Articles.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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