3-Hydroxybenzoyl-CoA: Difference between revisions

3-Hydroxybenzoyl-CoA
	; Chemical structure of 3-Hydroxybenzoyl-CoA
Names
	IUPAC name 3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl dihydrogen diphosphate]
	Systematic IUPAC name O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl] dihydrogen diphosphate
	Other names 3-Hydroxybenzoyl-coenzyme A; m-Hydroxybenzoyl-CoA; m-Hydroxybenzoyl-coenzyme A;
Identifiers
CAS Number	52301-52-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15484 ;
ChemSpider	10140112 ;
KEGG	C05195;
PubChem CID	11966118;
	InChI InChI=1S/C28H40N7O18P3S/c1-28(2,22(39)25(40)31-7-6-18(37)30-8-9-57-27(41)15-4-3-5-16(36)10-15)12-50-56(47,48)53-55(45,46)49-11-17-21(52-54(42,43)44)20(38)26(51-17)35-14-34-19-23(29)32-13-33-24(19)35/h3-5,10,13-14,17,20-22,26,36,38-39H,6-9,11-12H2,1-2H3,(H,30,37)(H,31,40)(H,45,46)(H,47,48)(H2,29,32,33)(H2,42,43,44)/t17-,20-,21-,22+,26-/m1/s1 Key: JTBCMZVWWNFUFR-TYHXJLICSA-N;
	SMILES CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O (O)O)C(C(=O)NCCC(=O)NCCSC(=O)C4=CC(=CC=C4)O)O;
Properties
Chemical formula	C28H40N7O18P3S
Molar mass	887.64 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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3-Hydroxybenzoyl-CoA is a molecule formed by condensing the thiol group of coenzyme A (CoA) with the carboxylic acid group of 3-hydroxybenzoic acid. Stable in acidic conditions, it is a tetraprotic acid due to the pyrophosphate and phosphate groups included. It derives from a benzoyl-CoA and a 3-hydroxybenzoic acid. In organisms such as plants, this can be formed using the 3-hydroxybenzoate—CoA ligase enzyme. This uses ATP, 3-hydroxybenzoate, and CoA as substrates.^[1]

It can be reduced to 3-hydroxycyclohexa-1,5-diene-1-carbonyl-CoA by reduced ferredoxin and adenosine triphosphate using the benzoyl-CoA reductase enzyme.^[2] in this two hydrogen atoms are added to the benzene ring in a dearomatizing process.

References

^ "BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase". www.brenda-enzymes.org.
^ "bcrA - Benzoyl-CoA reductase subunit A - Thauera aromatica - bcrA gene & protein". www.uniprot.org.

[1] "BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase". www.brenda-enzymes.org.

[2] "bcrA - Benzoyl-CoA reductase subunit A - Thauera aromatica - bcrA gene & protein". www.uniprot.org.

[1]

[2]

@@ Line 1: / Line 1: @@
-{{Promising draft}}
-{{AFC submission|t||ts=20201024110408|u=BQ20-VFernandez|ns=118|demo=}}<!-- Important, do not remove this line before article has been created. -->
 {{chembox
 | Name           =
-| ImageFile      = Image:Chemical structure of 3-Hydroxybenzoyl-CoA.jpg
+| ImageFile      = 3-Hydroxybenzoyl-CoA.svg
 | ImageName      = Chemical structure of 3-Hydroxybenzoyl-CoA
 | ImageSize      = 300px
 | ImageAlt       = Chemical structure of 3-Hydroxybenzoyl-CoA
 | ImageCaption   = Chemical structure of 3-Hydroxybenzoyl-CoA
+| IUPACName      = 3′-''O''-Phosphonoadenosine 5′-[(3''R'')-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl dihydrogen diphosphate]
-| OtherNames     = 3-Hydroxybenzoyl-CoA
+| SystematicName = ''O''<sup>1</sup>-<nowiki/>{[(2''R'',3''S'',4''R'',5''R'')-5-(6-Amino-9''H''-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} ''O''<sup>3</sup>-[(3''R'')-3-hydroxy-4-{[3-({2-[(3-hydroxybenzoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2-methyl-4-oxobutyl] dihydrogen diphosphate
--hydroxybenzoyl-coenzyme A
+| OtherNames     = {{bulletedlist|3-Hydroxybenzoyl-coenzyme A|''m''-Hydroxybenzoyl-CoA|''m''-Hydroxybenzoyl-coenzyme A}}
-m-hydroxybenzoyl-CoA
-| IUPACName      = S-[2-[3-<nowiki>[[</nowiki>(2''R'')-4-<nowiki>[[[</nowiki>(2''R'',3''S'',4''R'',5''R'')-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-hydroxybenzenecarbothioate
 | Section1       = {{Chembox Identifiers
+| CASNo = 52301-52-7
+| CASNo_Ref = {{Cascite|changed|}}
 | PubChem = 11966118
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
@@ Line 24: / Line 23: @@
 }}
 | Section2       = {{Chembox Properties
-| C=28 | H=40 | N=7 | O=18 | P=3 | S=1 |
+| C=28 | H=40 | N=7 | O=18 | P=3 | S=1
 }}
 | Section3       = {{Chembox Hazards
@@ Line 36: / Line 35: @@
 }}
-'''3-Hydroxybenzoyl-CoA''' is a molecule formed by condensing [[coenzyme A]] (CoA) with [[3-hydroxybenzoic acid]]. Stable in acidic conditions, it is a [[tetraprotic acid]] due to the [[pyrophosphate]] and phosphate groups included. In organisms such as plants, this can be formed using the [[3-hydroxybenzoate-CoA ligase]] enzyme. This uses [[ATP]], [[3-hydroxybenzoate]] and [[Coenzyme A|CoA]] as substrates.<ref>{{cite web |title=BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase |url=https://www.brenda-enzymes.org/enzyme.php?ecno=6.2.1.37 |website=www.brenda-enzymes.org}}</ref>
+'''3-Hydroxybenzoyl-CoA''' is a molecule formed by condensing the [[thiol group]] of [[coenzyme A]] (CoA) with the [[carboxylic acid]] group of [[3-hydroxybenzoic acid]]. Stable in acidic conditions, it is a [[tetraprotic acid]] due to the [[pyrophosphate]] and phosphate groups included. It derives from a [[benzoyl-CoA]] and a [[3-Hydroxybenzoic acid|3-hydroxybenzoic acid]]. In organisms such as plants, this can be formed using the [[3-hydroxybenzoate—CoA ligase]] enzyme. This uses [[Adenosine triphosphate|ATP]], [[3-hydroxybenzoate]], and [[Coenzyme A|CoA]] as substrates.<ref>{{cite web |title=BRENDA - Information on EC 6.2.1.37 - 3-hydroxybenzoate-CoA ligase |url=https://www.brenda-enzymes.org/enzyme.php?ecno=6.2.1.37 |website=www.brenda-enzymes.org}}</ref>
+It can be reduced to 3-hydroxycyclohexa-1,5-diene-1-carbonyl-CoA by reduced [[ferredoxin]] and [[adenosine triphosphate]] using the [[benzoyl-CoA reductase]] enzyme.<ref>{{cite web |title=bcrA - Benzoyl-CoA reductase subunit A - Thauera aromatica - bcrA gene & protein |url=https://www.uniprot.org/uniprot/O87876 |website=www.uniprot.org |language=en}}</ref> in this two hydrogen atoms are added to the benzene ring in a dearomatizing process.
 == References ==
-<!-- Inline citations added to your article will automatically display here. See en.wikipedia.org/wiki/WP:REFB for instructions on how to add citations. -->
 {{reflist}}
+{{DEFAULTSORT:Hydroxybenzoyl-CoA, 3-}}
+[[Category:Thioesters of coenzyme A]]