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Information on EC 1.14.12.19 - 3-phenylpropanoate dioxygenase
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1.14.12.19 3-phenylpropanoate dioxygenaseIUBMB Comments
This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation. It catalyses the insertion of both atoms of molecular oxygen into positions 2 and 3 of the phenyl ring of 3-phenylpropanoate or (2E)-3-phenylprop-2-enoate.
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The expected taxonomic range for this enzyme is: Bacteria, Archaea
Reaction Schemes
Synonyms
3-phenylpropionate dioxygenase, hcaa1a2cd, hca dioxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-phenylpropionate dioxygenase
Hca dioxygenase
HcaA1A2CD
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E)-3-phenylprop-2-enoate + NADH + H+ + O2 = (2E)-3-(2,3-dihydroxyphenyl)prop-2-enoate + NAD+
(2)
-
-
-
3-phenylpropanoate + NADH + H+ + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
3-phenylpropanoate + NADH + H+ + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
-
-
-
-
3-phenylpropanoate + NADH + H+ + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
(1)
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
3-phenylpropanoate,NADH:oxygen oxidoreductase (2,3-hydroxylating)
This enzyme catalyses a step in the pathway of phenylpropanoid compounds degradation. It catalyses the insertion of both atoms of molecular oxygen into positions 2 and 3 of the phenyl ring of 3-phenylpropanoate or (2E)-3-phenylprop-2-enoate.
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CAS REGISTRY NUMBER
COMMENTARY
105503-66-0
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-phenylpropionate + NADH + H+ + O2
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
-
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
-
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
-
-
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
-
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
enables utilization of 3-phenylpropionate as carbon source, important role in wine making, aging and storage
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
involved in oxidative stress response
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
-
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
-
-
-
?
cinnamic acid + NADH + H+ + O2
cinnamic acid-2,3-dihydrodiol + NAD+
-
-
-
-
?
cinnamic acid + NADH + H+ + O2
cinnamic acid-2,3-dihydrodiol + NAD+
-
HcaE is involved in degradation of endogenous cinnamic acid
-
-
?
cinnamic acid + NADH + H+ + O2
cinnamic acid-2,3-dihydrodiol + NAD+
-
HcaE is involved in degradation of endogenous cinnamic acid
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-phenylpropionate + NADH + H+ + O2
3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-(2,3-dihydroxyphenyl)propionate + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
enables utilization of 3-phenylpropionate as carbon source
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
enables utilization of 3-phenylpropionate as carbon source, important role in wine making, aging and storage
-
-
?
3-phenylpropionate + NADH + H+ + O2
3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid + NAD+
-
involved in oxidative stress response
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Cinnamic acid
-
induces the expression of the hca operon, the plu2201 and plu2202 genes, and stlA expression
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
and enzyme deficiency strains obtained from mutagenesis with ethylmethane sulfonate
-
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
Hca dioxygenase is involved in the consumption of endogenous cinnamic acid but is not required for 3,5-dihydroxy-4-isopropylstilbene antibiotic production. Disruption of hcaE abolishes the stationary-phase-dependent decrease of extracellular cinnamic acid evidenced in the wild-type strain, hcaE disruption increases stlA expression, thus enhancing cinnamic acid synthesis. Effect of cinnamic acid on plu2201 and plu2202 expression requires HcaR, whereas HcaR is not required for cinnamic acid-induced stlA expression
physiological function
-
Hca dioxygenase is involved in the consumption of endogenous cinnamic acid but is not required for 3,5-dihydroxy-4-isopropylstilbene antibiotic production. Disruption of hcaE abolishes the stationary-phase-dependent decrease of extracellular cinnamic acid evidenced in the wild-type strain, hcaE disruption increases stlA expression, thus enhancing cinnamic acid synthesis. Effect of cinnamic acid on plu2201 and plu2202 expression requires HcaR, whereas HcaR is not required for cinnamic acid-induced stlA expression
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). HCAF_ECODH
Escherichia coli (strain K12 / DH10B)
172
0
20579
Swiss-Prot
-
HCAF_ECOLC
Escherichia coli (strain ATCC 8739 / DSM 1576 / NBRC 3972 / NCIMB 8545 / WDCM 00012 / Crooks)
172
0
20565
Swiss-Prot
-
HCAF_ECOLU
Escherichia coli O17:K52:H18 (strain UMN026 / ExPEC)
172
0
20606
Swiss-Prot
-
HCAF_ECOSM
Escherichia coli (strain SMS-3-5 / SECEC)
172
0
20565
Swiss-Prot
-
HCAF_PHOLL
Photorhabdus laumondii subsp. laumondii (strain DSM 15139 / CIP 105565 / TT01)
180
0
21783
Swiss-Prot
-
HCAF_SHIBS
Shigella boydii serotype 4 (strain Sb227)
172
0
20527
Swiss-Prot
-
HCAF_SHIF8
Shigella flexneri serotype 5b (strain 8401)
172
0
20613
Swiss-Prot
-
HCAE_PHOLL
Photorhabdus laumondii subsp. laumondii (strain DSM 15139 / CIP 105565 / TT01)
453
0
51322
Swiss-Prot
-
HCAE_SHIBS
Shigella boydii serotype 4 (strain Sb227)
453
0
51049
Swiss-Prot
-
HCAE_SHIF8
Shigella flexneri serotype 5b (strain 8401)
453
0
51120
Swiss-Prot
-
HCAF_ECO24
Escherichia coli O139:H28 (strain E24377A / ETEC)
172
0
20579
Swiss-Prot
-
HCAF_ECO55
Escherichia coli (strain 55989 / EAEC)
172
0
20579
Swiss-Prot
-
HCAF_ECO5E
Escherichia coli O157:H7 (strain EC4115 / EHEC)
172
0
20526
Swiss-Prot
-
HCAF_ECO7I
Escherichia coli O7:K1 (strain IAI39 / ExPEC)
172
0
20565
Swiss-Prot
-
HCAF_ECOBW
Escherichia coli (strain K12 / MC4100 / BW2952)
172
0
20579
Swiss-Prot
-
A0A7D4X6K7_9GAMM
172
0
20410
TrEMBL
-
A0A7K1JCI4_9MYCO
174
0
20109
TrEMBL
-
A0A7K3MAK6_9ACTN
173
0
20373
TrEMBL
-
A0A5C4RD94_PHOLU
453
0
51226
TrEMBL
-
A0A5B8CFU0_SPHSA
191
0
21939
TrEMBL
-
A0A8E0KEV5_ECOLX
453
0
51109
TrEMBL
-
A0A2S6Q7P8_9PROT
165
0
18749
TrEMBL
-
D2AHB3_SHIF2
Shigella flexneri serotype X (strain 2002017)
172
0
20565
TrEMBL
-
A0A518BHJ3_9BACT
364
0
40945
TrEMBL
-
A0A1J5SJJ4_9ZZZZ
368
0
42776
TrEMBL
other Location (Reliability: 2)
A0A7I6TXM3_9ENTR
453
0
51191
TrEMBL
-
B9L3H6_THERP
Thermomicrobium roseum (strain ATCC 27502 / DSM 5159 / P-2)
184
0
21766
TrEMBL
-
A0A6B9BE26_MYCAV
427
0
49076
TrEMBL
-
A0A553A191_9MYCO
119
0
12795
TrEMBL
-
A0A7G7MBV7_9PSEU
180
0
20429
TrEMBL
-
A0A329VP96_9GAMM
453
0
51199
TrEMBL
-