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Information on EC 2.3.1.233 - 1,3,6,8-tetrahydroxynaphthalene synthase
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EC Tree
2.3.1.233 1,3,6,8-tetrahydroxynaphthalene synthaseIUBMB Comments
Isolated from the fungus Colletotrichum lagenarium , and the bacteria Streptomyces coelicolor [2,3] and Streptomyces peucetius . It only uses malonyl-CoA, without invovement of acetyl-CoA.
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Word Map
- 2.3.1.233
- polyketide
- coelicolor
- flaviolin
- synthases
-
streptomycete
- venezuelae
- accase
- griseus
-
starter
- chalcone
- synthesis
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
1,3,6,8-tetrahydroxynaphthalene synthase, pks iii, sco1206, thn synthase, socechs1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,3,6,8-tetrahydroxynaphthalene synthase
PhlD
PKS
PKS III
PKS1
RppA
SCO1206
THN synthase
THNS
type III polyketide synthase
PKS1
-
-
-
-
RppA
-
-
-
-
SCO1206
-
-
-
-
THNS
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5 malonyl-CoA = 1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
condensation
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA C-acyl transferase (1,3,6,8-tetrahydroxynaphthalene forming)
Isolated from the fungus Colletotrichum lagenarium [1], and the bacteria Streptomyces coelicolor [2,3] and Streptomyces peucetius [4]. It only uses malonyl-CoA, without invovement of acetyl-CoA.
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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
acetoacetyl-CoA + methylmalonyl-CoA
3,6-dimethyl-4-hydroxy-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
butyryl-CoA
4-hydroxy-6-propyl-2-pyrone + 4-hydroxy-6-(2'-oxopentyl)-2-pyrone + 1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
21% activity compared to acetoacetyl-CoA
-
-
?
hexanoyl-CoA
4-hydroxy-6-pentyl-2-pyrone + 4-hydroxy-6-(2'-oxoheptyl)-2-pyrone + CoA + CO2 + H2O
isobutyryl-CoA
4-hydroxy-6-isopropyl-2-pyrone + 4-hydroxy-6-(3'-methyl-2'-oxopropyl)-2-pyrone + CoA + CO2 + H2O
-
7% activity compared to acetoacetyl-CoA
-
-
?
isovaleryl-CoA
4-hydroxy-6-isobutyl-2-pyrone + 4-hydroxy-6-(4'-methyl-2'-oxopentyl)-2-pyrone + CoA + CO2 + H2O
-
13% activity compared to acetoacetyl-CoA
-
-
?
lauroyl-CoA
1-(2,4,6-trihydroxyphenyl)-dodecan-1-one + 4-hydroxy-6-(2-oxotridecyl)-2H-pyran-2-one + CoA + CO2 + H2O
malonyl-CoA
5 1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
octanoyl-CoA
6-heptyl-4-hydroxy-2-pyrone + 4-hydroxy-6-(2'-oxononyl)-2-pyrone + 4-hydroxy-6-(2',4',6'-trioxotridecyl)-2-pyrone + CoA + CO2 + H2O
-
6% activity compared to acetoacetyl-CoA
-
-
?
octanoyl-CoA + malonyl-CoA
4-hydroxy-6-(2',4',6'-trioxotridecyl)-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
phenylacetyl-CoA
6-benzyl-4-hydroxy-2-pyrone + 4-hydroxy-6-(2'-oxo-3'-phenylpropyl)-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
acetoacetyl-CoA
4-hydroxy-6-methyl-2-pyrone + CoA + CO2 + H2O
-
100% activity
-
-
?
acetoacetyl-CoA + 2 malonyl-CoA
4-hydroxy-6-methyl-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
acetoacetyl-CoA + 2 malonyl-CoA
4-hydroxy-6-methyl-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
benzoyl-CoA + 2 malonyl-CoA
4-hydroxy-6-phenyl-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
-
?
benzoyl-CoA + 2 malonyl-CoA
4-hydroxy-6-phenyl-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
-
?
hexanoyl-CoA
4-hydroxy-6-pentyl-2-pyrone + 4-hydroxy-6-(2'-oxoheptyl)-2-pyrone + CoA + CO2 + H2O
-
-
-
-
?
hexanoyl-CoA
4-hydroxy-6-pentyl-2-pyrone + 4-hydroxy-6-(2'-oxoheptyl)-2-pyrone + CoA + CO2 + H2O
-
43% activity compared to acetoacetyl-CoA
-
-
?
hexanoyl-CoA + 2 malonyl-CoA
4-hydroxy-6-pentyl-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
-
?
hexanoyl-CoA + 2 malonyl-CoA
4-hydroxy-6-pentyl-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
-
?
lauroyl-CoA
1-(2,4,6-trihydroxyphenyl)-dodecan-1-one + 4-hydroxy-6-(2-oxotridecyl)-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
?
lauroyl-CoA
1-(2,4,6-trihydroxyphenyl)-dodecan-1-one + 4-hydroxy-6-(2-oxotridecyl)-2H-pyran-2-one + CoA + CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
additional information
?
-
-
does not use acetyl-CoA as substrate
-
-
?
additional information
?
-
-
less than 1% activity with acetyl-CoA, decanoyl-CoA, benzoyl-CoA, phenylacetyl-CoA, crotonoyl-CoA, and tiglyl-CoA
-
-
?
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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
malonyl-CoA
5 1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
additional information
?
-
-
does not use acetyl-CoA as substrate
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
5 malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + 5 CoA + 5 CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
malonyl-CoA
1,3,6,8-tetrahydroxynaphthalene + CoA + CO2 + H2O
-
-
-
-
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0014
malonyl-CoA
-
mutant enzyme C184S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
0.0023
malonyl-CoA
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
0.0085
malonyl-CoA
-
mutant enzyme C171S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
0.93
malonyl-CoA
-
in 100 mM Tris-HCl (pH 7.5), 1 mM EDTA, 1 mM 2-mercaptoethanol, at 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.013
malonyl-CoA
-
in 100 mM Tris-HCl (pH 7.5), 1 mM EDTA, 1 mM 2-mercaptoethanol, at 30°C
45.7
malonyl-CoA
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
46.5
malonyl-CoA
-
mutant enzyme C171S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
79.2
malonyl-CoA
-
mutant enzyme C184S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.55
malonyl-CoA
-
mutant enzyme C171S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
1.97
malonyl-CoA
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
5.53
malonyl-CoA
-
mutant enzyme C184S, in 100 mM Tris-HCl buffer (pH 7.5), at 22°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
-
the enzyme catalyses the synthesis of 1,3,6,8-tetrahydroxynaphthalene which is the key intermediate of melanin biosynthesis
metabolism
the enzyme catalyzes a major step in the biosynthetic pathway of phlorotannins (i.e., the synthesis of phloroglucinol monomers from malonyl-CoA)
metabolism
-
the enzyme catalyzes a major step in the biosynthetic pathway of phlorotannins (i.e., the synthesis of phloroglucinol monomers from malonyl-CoA)
-
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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). RPPA_STRC0
377
0
39081
Swiss-Prot
-
RPPA_STRCO
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
374
0
40934
Swiss-Prot
-
A0A841BJ88_9ACTN
348
0
37258
TrEMBL
-
A0A2S6R8F5_9PROT
355
0
38054
TrEMBL
-
A0A645H7T9_9ZZZZ
97
0
10412
TrEMBL
other Location (Reliability: 2)
A0A2S6U8G4_9PROT
348
0
36533
TrEMBL
-
A0A101RMZ6_9ACTN
394
0
42045
TrEMBL
-
A0A6J4J722_9ACTN
366
0
39712
TrEMBL
-
A0A399F763_9DEIN
354
0
37059
TrEMBL
-
A0A2S6TW46_9PROT
348
0
36787
TrEMBL
-
A0A7R8P7R0_9ACTN