InChI=1S/C12H14Cl2O4/c1-2-3-4-5-6(15)7-10(16)8(13)12(18)9(14)11(7)17/h16-18H,2-5H2,1H3 |
WLWLDMLTAFSEDI-UHFFFAOYSA-N |
C(CCCCC)(=O)C1=C(C(=C(C(=C1O)Cl)O)Cl)O |
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eukaryotic metabolite
Any metabolite produced during a metabolic reaction in eukaryotes, the taxon that include members of the fungi, plantae and animalia kingdoms.
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View more via ChEBI Ontology
Outgoing
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(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
has role
eukaryotic metabolite
(CHEBI:75763)
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
is a
aromatic ketone
(CHEBI:76224)
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
is a
benzenetriol
(CHEBI:22707)
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
is a
dichlorobenzene
(CHEBI:23697)
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
is conjugate acid of
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1−)
(CHEBI:90398)
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Incoming
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1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one
(CHEBI:64598)
has functional parent
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one(1−)
(CHEBI:90398)
is conjugate base of
(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
(CHEBI:90396)
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1-(3,5-dichloro-2,4,6-trihydroxyphenyl)hexan-1-one
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3,5-dichloro-THPH
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SUBMITTER
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Cl2-THPH
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ChEBI
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dichloro-THPH
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ChEBI
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10184570
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Reaxys Registry Number
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Reaxys
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118222-71-2
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CAS Registry Number
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Reaxys
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Kay RR (1998) The biosynthesis of differentiation-inducing factor, a chlorinated signal molecule regulating Dictyostelium development. The Journal of biological chemistry 273, 2669-2675 (Source: SUBMITTER) [PubMed:9446571] [show Abstract] Differentiation-inducing factor (DIF)-1 is a chlorinated alkyl phenone released by developing Dictyostelium amoebae, which induces them to differentiate into stalk cells. A biosynthetic pathway for DIF-1 is proposed from labeling, inhibitor, and enzymological experiments. Cells incorporate 36Cl- into DIF-1 during development, showing that the chlorine atoms originate from chloride ions; peak incorporation is at the first finger stage. DIF-1 synthesis can be blocked by cerulenin, a polyketide synthase inhibitor, suggesting that it is made from a polyketide. This is most likely the C12 polyketide (2,4,6-trihydroxyphenyl)-1-hexan-1-one (THPH). Feeding experiments confirm that living cells can convert THPH to DIF-1. Conversion requires both chlorination and methylation of THPH, and enzymatic activities able to do this exist in cell lysates. The chlorinating activity, assayed using 36Cl-, is stimulated by H2O2 and requires both soluble and particulate components. It is specific for THPH and does not use this compound after O-methylation. The methyltransferase is soluble, uses S-adenosyl-L-methionine as a co-substrate, has a Km for dichloro-THPH of about 1.1 microM, and strongly prefers this substrate to close analogues. Both chlorinating and methyltransferase activities increase in development in parallel with DIF-1 production, and both are greatly reduced in a mutant strain that makes little DIF-1. It is proposed that DIF-1 is made by the initial assembly of a C12 polyketide skeleton, which is then chlorinated and methylated. |
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