Coenzyme A

Molecular FormulaC₂₁H₃₆N₇O₁₆P₃S
Average mass767.534 Da
Monoisotopic mass767.115234 Da
ChemSpider ID79067

- 5 of 5 defined stereocentres

More details:

Systematic name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl dihydrogen dipho sphate (non-preferred name)
SMILES
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O
Std. InChi
InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
Std. InChIKey
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
Cite this record
CSID:79067, http://www.chemspider.com/Chemical-Structure.79067.html (accessed 20:41, Oct 3, 2023)

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Names and Synonyms
Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl dihydrogen dipho sphate [ACD/IUPAC Name]

[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]methyl-(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyldihydrogendiphosp hat [German] [ACD/IUPAC Name]

201-619-0 [EINECS]

85-61-0 [RN]

Adenosine, 5'-O-[hydroxy[[hydroxy[(3R)-3-hydroxy-4-[[3-[(2-mercaptoethyl)amino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutoxy]phosphinyl]oxy]phosphinyl]-, 3'-(dihydrogen phosphate) [ACD/Index Name]

CoA

CoASH

Coenzym A

Coenzyme A [Wiki]

More...

coenzyme-A

co-enzyme-A

Dihydrogénodiphosphate de [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tétrahydro-2-furanyl]méthyle et de (3R)-3-hydroxy-2,2-diméthyl-4-oxo-4-({3-oxo-3-[(2-sulfanyléthyl)amino]pr opyl}amino)butyle [French] [ACD/IUPAC Name]

HSCoA

HS-CoA

SAA04E81UX

[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl [hydroxy-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butoxy]phosphoryl] hydrogen phosphate

[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate

143180-18-1 [RN]

18-CoA-18-oxo-dinor-LTB4

1VU

3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}

3'-phosphoadenosine-(5')diphospho(4')pantatheine

77809 [Beilstein]

9H-purin-6-amine,9-[5-O-[hydroxy[[hydroxy[[(3R)-3-hydroxy-4-[[3-[(2-mercaptoethyl)amino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutyl]oxy]phosphinyl]oxy]phosphinyl]-3-O-phosphono-β-D-ribofuranosyl]-

acetoacetyl-coenzyme a

Acetyl coenzyme A

ACO

Adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) P'-[(R)-3-hydroxy-4-[[3-[(2-mercaptoethyl)amino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutyl] ester

Adenosine 5'-(trihydrogen diphosphate), 3'-(dihydrogen phosphate), P'-[3-hydroxy-4-[[3-[(2-mercaptoethyl)amino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutyl] ester, (R)-

Aluzime

CAA

CAO

co-A

Coali

Coalip

CoA-SH

Co-A-SH

Coenzyme A|coenzyme A

Coenzyme ASH

co-enzyme-A|CoA

Koenzym A

Lucina

Malonyl-coenzyme A

MFCD06795839

MLC

pCoenzyme ASH

Phosphoteric T-C6

Propionyl coenzyme A

Thiol-CoA

UNII:SAA04E81UX

UNII-SAA04E81UX

Less...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

c0919 [DBID]

CHEBI:15346 [DBID]

Experimental data
Predicted - ACD/Labs
Predicted - ChemAxon

Miscellaneous

Chemical Class:

A thiol comprising a panthothenate unit in phosphoric anhydride linkage with a 3',5'-adenosine diphosphate unit; and an aminoethanethiol unit. ChEBI CHEBI:15346

Compound Source:

1,4-dihydroxy-2-naphthoate biosynthesis II (plants) PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

2-O-acetyl-3-O-trans-coutarate biosynthesis PlantCyc CO-A, CO-A

3-amino-3-phenylpropanoyl-CoA biosynthesis PlantCyc CO-A

3-hydroxypropanoate + ATP + coenzyme A + NADPH + H+ -> propanoyl-CoA + AMP + NADP+ + diphosphate + H2O PlantCyc CO-A, CO-A

4-hydroxybenzoate biosynthesis V PlantCyc CO-A

4-hydroxycoumarin and dicoumarol biosynthesis PlantCyc CO-A, CO-A

6-gingerol analog biosynthesis (engineered) PlantCyc CO-A, CO-A

6-methoxymellein biosynthesis PlantCyc CO-A

acetate conversion to acetyl-CoA PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A

acetate formation from acetyl-CoA I PlantCyc CO-A, CO-A

acetate formation from acetyl-CoA II PlantCyc CO-A, CO-A

acridone alkaloid biosynthesis PlantCyc CO-A, CO-A

adlupulone and adhumulone biosynthesis PlantCyc CO-A

Aegilops tauschii PlantCyc CO-A

ajmaline and sarpagine biosynthesis PlantCyc CO-A, CO-A, CO-A

aliphatic glucosinolate biosynthesis, side chain elongation cycle PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

alkane biosynthesis II PlantCyc CO-A

alliin metabolism PlantCyc CO-A

aloesone biosynthesis I PlantCyc CO-A

aloesone biosynthesis II PlantCyc CO-A

Amaranthus hypochondriacus PlantCyc CO-A

Amborella trichopoda PlantCyc CO-A

Anacardium occidentale PlantCyc CO-A

Ananas comosus PlantCyc CO-A

anthocyanidin acylglucoside and acylsambubioside biosynthesis PlantCyc CO-A

anthocyanidin modification (Arabidopsis) PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

apigenin glycosides biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Aquilegia coerulea PlantCyc CO-A

Arabidopsis halleri PlantCyc CO-A

Arabidopsis lyrata PlantCyc CO-A

Arabidopsis thaliana col PlantCyc CO-A

arachidonate biosynthesis I (6-desaturase, lower eukaryotes) PlantCyc CO-A, CO-A, CO-A

aromatic polyketides biosynthesis PlantCyc CO-A

Asparagus officinalis PlantCyc CO-A

aucuparin biosynthesis PlantCyc CO-A, CO-A, CO-A

barbaloin biosynthesis PlantCyc CO-A, CO-A

benzoate degradation II (aerobic and anaerobic) PlantCyc CO-A

benzoylanthranilate biosynthesis PlantCyc CO-A, CO-A

benzoyl-CoA biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Beta vulgaris subsp. vulgaris PlantCyc CO-A

biochanin A conjugates interconversion PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Boechera stricta PlantCyc CO-A

Brachypodium distachyon PlantCyc CO-A

Brassica napus PlantCyc CO-A

Brassica oleracea var. capitata PlantCyc CO-A

Brassica oleracea var. oleracea PlantCyc CO-A

Brassica rapa FPsc PlantCyc CO-A

Brassica rapa subsp. pekinensis PlantCyc CO-A

caffeoylglucarate biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Calotropis gigantea PlantCyc CO-A

Camptotheca acuminata PlantCyc CO-A

cannabinoid biosynthesis PlantCyc CO-A, CO-A, CO-A

Cannabis sativa PlantCyc CO-A

capsaicin biosynthesis PlantCyc CO-A, CO-A

Capsella grandiflora PlantCyc CO-A

Capsella rubella PlantCyc CO-A

capsiconiate biosynthesis PlantCyc CO-A, CO-A

Capsicum annuum PlantCyc CO-A

Carica papaya PlantCyc CO-A

Catharanthus roseus PlantCyc CO-A

Chenopodium quinoa PlantCyc CO-A

Chlamydomonas reinhardtii PlantCyc CO-A

Chromochloris zofingiensis PlantCyc CO-A

Cicer arietinum PlantCyc CO-A

Citrus clementina PlantCyc CO-A

Citrus sinensis PlantCyc CO-A

cocaine biosynthesis PlantCyc CO-A

Coccomyxa subellipsoidea C-169 PlantCyc CO-A

coenzyme A biosynthesis II (eukaryotic) PlantCyc CO-A, CO-A, CO-A

colchicine biosynthesis PlantCyc CO-A

colupulone and cohumulone biosynthesis PlantCyc CO-A

Corchorus capsularis PlantCyc CO-A

coumarins biosynthesis (engineered) PlantCyc CO-A, CO-A

crotonyl-CoA/ethylmalonyl-CoA/hydroxybutyryl-CoA cycle (engineered) PlantCyc CO-A

Cucumis sativus PlantCyc CO-A

curcuminoid biosynthesis PlantCyc CO-A

cyanidin dimalonylglucoside biosynthesis PlantCyc CO-A, CO-A, CO-A

daidzein conjugates interconversion PlantCyc CO-A, CO-A, CO-A

Daucus carota subsp. sativus PlantCyc CO-A

Dianthus caryophyllus PlantCyc CO-A

dimorphecolate biosynthesis PlantCyc CO-A, CO-A

Dioscorea rotundata PlantCyc CO-A

docosahexaenoate biosynthesis I (lower eukaryotes) PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

epoxypseudoisoeugenol-2-methylbutanoate biosynthesis PlantCyc CO-A

esculetin biosynthesis PlantCyc CO-A, CO-A, CO-A

ethanol degradation I PlantCyc CO-A, CO-A

ethanol degradation II PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A

ethanol degradation IV PlantCyc CO-A, CO-A

Eucalyptus grandis PlantCyc CO-A

Eutrema salsugineum PlantCyc CO-A

flavonoid di-C-glucosylation PlantCyc CO-A, CO-A, CO-A

flavonol acylglucoside biosynthesis I - kaempferol derivatives PlantCyc CO-A

flavonol acylglucoside biosynthesis II - isorhamnetin derivatives PlantCyc CO-A

flavonol acylglucoside biosynthesis III - quercetin derivatives PlantCyc CO-A

formononetin conjugates interconversion PlantCyc CO-A, CO-A, CO-A

Fragaria vesca subsp. vesca PlantCyc CO-A

furaneol and mesifurane biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

furaneol biosynthesis PlantCyc CO-A

genistein conjugates interconversion PlantCyc CO-A, CO-A, CO-A

gentiodelphin biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

geranyl acetate biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

glucosinolate biosynthesis from dihomomethionine PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

glucosinolate biosynthesis from homomethionine PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

glutathione-mediated detoxification II PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Glycine max PlantCyc CO-A

glycolate and glyoxylate degradation II PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Gossypium raimondii PlantCyc CO-A

Helianthus annuus PlantCyc CO-A

hexanoyl-CoA + 3 malonyl-CoA + 3 H+ = 3,5,7-trioxododecanoyl-CoA + 3 CO2 + 3 coenzyme A PlantCyc CO-A, CO-A, CO-A

hinokiresinol biosynthesis PlantCyc CO-A, CO-A

hordatine biosynthesis PlantCyc CO-A, CO-A

Hordeum vulgare subsp. vulgare PlantCyc CO-A

Humulus lupulus var. lupulus PlantCyc CO-A

hydroxycinnamate sugar acid ester biosynthesis PlantCyc CO-A

hydroxycinnamic acid serotonin amides biosynthesis PlantCyc CO-A, CO-A, CO-A

hydroxycinnamic acid tyramine amides biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

hydroxylated fatty acid biosynthesis (plants) PlantCyc CO-A

hyoscyamine and scopolamine biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

hyperforin and adhyperforin biosynthesis PlantCyc CO-A

hyperxanthone E biosynthesis PlantCyc CO-A

hypoglycin biosynthesis PlantCyc CO-A, CO-A

IAA biosynthesis VII PlantCyc CO-A, CO-A

icosapentaenoate biosynthesis I (lower eukaryotes) PlantCyc CO-A, CO-A

isoprene biosynthesis II (engineered) PlantCyc CO-A

juniperonate biosynthesis PlantCyc CO-A

kaempferol triglucoside biosynthesis PlantCyc CO-A, CO-A, CO-A

Kalanchoe fedtschenkoi PlantCyc CO-A

Kalanchoe laxiflora PlantCyc CO-A

Leersia perrieri PlantCyc CO-A

L-homomethionine biosynthesis PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A

Linum usitatissimum PlantCyc CO-A

L-lysine biosynthesis I PlantCyc CO-A

L-ornithine biosynthesis I PlantCyc CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A, CO-A,