Rule bt0008

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Pattern 2460
vic-Dihydroxybenzenoid -> extradiol ring cleavage


Aerobic Likelihood:              Likely

EAWAG-BBD Reaction(s):
2'-Aminobiphenyl-2,3-diol -----> 2-Hydroxy-6-oxo-(2'-aminophenyl)-hexa-2E,4Z-dienoate (reacID# r0457)
Catechol -----> 2-Hydroxy-cis,cis-muconate semialdehyde (reacID# r0307)
3-Chlorocatechol -----> 3-Chloro-2-hydroxymuconic semialdehyde (reacID# r1022)
4-Chlorocatechol -----> 5-Chloro-2-hydroxymuconic semialdehyde (reacID# r0287)
1,1-Dichloro-2-(dihydroxy-4'-chorophenyl)-2-(4'-chlorophenyl)ethylene -----> 6-Oxo-2-hydroxy-7-(4'-chlorophenyl)-3,8,8-trichloroocta-2Z,4Z,7-trienoate (reacID# r0442)
2,3-Dihydroxy DDT -----> 6-Oxo-2-hydroxy-7-(4'-chlorophenyl)-3,8,8,8-tetrachloroocta-2Z,4Z-dienoate (reacID# r0452)
2,3-Dihydroxy-2'-carboxybiphenyl -----> 2-Hydroxy-6-oxo-6-(2-carboxyphenyl)-hexa-2,4-dienoate (reacID# r1041)
2,3-Dihydroxy-4'-chlorobiphenyl -----> 2-Hydroxy-6-oxo-6-(4'-chlorophenyl)-hexa-2,4-dienoate (reacID# r0135)
3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione -----> (3E,1Z)-4,5-9,10-Diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate (reacID# r1151)
2,3-Dihydroxy-p-cumate -----> 2-Hydroxy-3-carboxy-6-oxo-7-methylocta-2,4-dienoate (reacID# r0397)
3,4-Dihydroxybenzoate -----> 2-Hydroxy-4-carboxymuconate semialdehyde (reacID# r0144)
2,3-Dihydroxybiphenyl -----> 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate (reacID# r0390)
2,3-Dihydroxyethylbenzene -----> 2-Hydroxy-6-oxoocta-2,4-dienoate (reacID# r0310)
3-(2,3-Dihydroxyphenyl)propionate -----> 2-Hydroxy-6-keto-nona-2,4-dienedioate (reacID# r0437)
3,4-Dihydroxyphenylacetate -----> trans,cis-5-Carboxymethyl-2-hydroxymuconate semialdehyde (reacID# r0364)
3,4-Dimethylcatechol -----> 2-Hydroxy-5-methyl-6-oxohepta-2,4-dienoate (reacID# r1555)
3,6-Dimethylcatechol -----> 2-Hydroxy-3-methyl-6-oxohepta-2,4-dienoate (reacID# r1561)
4,5-Dimethylcatechol -----> 2-Hydroxy-4,5-dimethyl-6-oxohexa-2,4-dienoate (reacID# r1558)
Isobutylcatechol -----> 5-Formyl-2-hydroxy-7-methyl-octa-2,4-dienoate (reacID# r1737)
3-Methylcatechol -----> cis,cis-2-Hydroxy-6-oxohept-2,4-dienoate (reacID# r0262)
4-Methylcatechol -----> 2-Hydroxy-5-methyl-cis,cis-muconic semialdehyde (reacID# r0180)
3-O-Methylgallate -----> 4-Carboxy-2-hydroxy-6-methoxy-6-oxohexa-2,4-dienoate (reacID# r1638)
3-Sulfocatechol -----> 2-Hydroxymuconate (reacID# r0219)
2,6,7-Trihydroxybenzimidazole -----> (2Z)-3-(4-Formyl-2-hydroxy-1H-imidazol-5-yl)-2-hydroxyprop-2-enoate (reacID# r1776)
2,2',3-Trihydroxybiphenyl -----> 2-Hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate (reacID# r0027)
2,2',3-Trihydroxydiphenylether -----> 2-Hydroxy-6-oxo-6-(2-hydroxyphenoxy)hexa-2,4-dienoate (reacID# r0572)
2,3,5-Trihydroxytoluene -----> 2,4,6-Trioxoheptanoate (reacID# r0093)
3-Vinylcatechol -----> (2E,4Z)-2-Hydroxy-6-oxoocta-2,4,7-trienoate (reacID# r0258)

Comments:
If the aromatic single catechol ring is not symmetric, the compound is cleaved on both sides of the vic-hydroxyl groups. Cleavage at both sides is known for compounds such as protocatechuate. Other single ring compounds may only be cleaved on one side. Biphenyl catechols are only cleaved at the side closest to the second phenyl ring. This rule is part of the upper extradiol ring cleavage super rule.

Similarities:
bt0041: 1-Amino-2-hydroxy-3-unsubstituted benzenoid --> distal extradiol ring cleavage
bt0069: 1,4-Dihydroxy-2-halobenzenoid --> 2-Halomaleylacetate
bt0174: 1,4-Dihydroxy-2-substituted --> intrasubstituent ring cleavage
bt0254: vic-Dihydroxyaromatic --> intradiol ring cleavage
bt0297: Hydroquinone derivative --> cis,cis-4-Ketomuconic semialdehyde derivative

Contact Us if you have any comments on rule bt0008.
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Page Author(s): Bo Kyeng Hou, Dave Roe and Michael Turnbull
August 16, 2010

This is the EAWAG-BBD biotransformation rule, ruleID# bt0008.
It was generated on September 19, 2017 6:45:53 AM CDT.

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