Coenzyme A

Details

• Internal ID: 3e63ed12-0f22-4227-a054-3916ef9ce6b0
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside 3,5-bisphosphates > Coenzyme A and derivatives
• IUPAC Name: [[(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
• 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
• InChI Key: RGJOEKWQDUBAIZ-IBOSZNHHSA-N
• Popularity: 17,168 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆N₇O₁₆P₃S
• Molecular Weight: 767.50 g/mol
• Exact Mass: 767.11521025 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: -5.80
• Atomic LogP (AlogP): -1.67
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 18

Synonyms

• CoASH
• 85-61-0
• CoA
• CoA-SH
• Zeel
• Depot-Zeel
• HSCoA
• Aluzime
• Coenzym A
• co-enzyme-A
• Coenzyme ASH
• Phosphoteric T-C6
• HS-CoA
• COENZYME_A
• SAA04E81UX
• CHEBI:15346
• 3'-phosphoadenosine-(5')diphospho(4')pantatheine
• [[(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
• Co-A-SH
• Reduced CoA
• [(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
• 3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}
• 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
• UNII-SAA04E81UX
• Coalip
• Lucina
• coenzymes A
• S-propanoate
• coenzyme-A
• CoA hydrate
• Koenzym A
• S-propanoic acid
• Thiol-CoA
• S-propanoate CoA
• S-propionate CoA
• D-Coenzyme A
• Coenzyme A-SH
• 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)-
• 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)-
• co-A
• EINECS 201-619-0
• S-propanoate Coenzyme A
• S-propionate Coenzyme A
• COENZYME A [MI]
• COENZYME A [HPUS]
• COENZYME A [INCI]
• 85-61-0 (anhydrous)
• COENZYME A [MART.]
• COENZYME A [WHO-DD]
• GTPL3044
• CHEMBL1213327
• SCHEMBL18180012
• MCC2008
• RGJOEKWQDUBAIZ-IBOSZNHHSA-N
• 4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-N-((Z)-3-hydroxy-3-((2-mercaptoethyl)imino)propyl)-3,3-dimethylbutanimidic acid
• BDBM50367033
• AKOS025310810
• DB01992
• HY-128851
• CS-0100923
• C00010
• A904100
• EN300-20600009
• (((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-2-(((hydroxy((hydroxy((R)-3-hydroxy-2,2-dimethyl-3-((2-((2-sulfanylethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphoryl)oxy)phosphoryl)oxy)methyl)oxolan-3-yl)oxy)phosphonic acid
• [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl dihydrogen diphosphate (non-preferred name)
• [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 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-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• 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-beta-D-ribofuranosyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8652	86.52%
Caco-2	-	0.8707	87.07%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.3614	36.14%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8902	89.02%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8349	83.49%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.7120	71.20%
P-glycoprotein substrate	+	0.7589	75.89%
CYP3A4 substrate	+	0.6850	68.50%
CYP2C9 substrate	-	0.6044	60.44%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.8203	82.03%
CYP2C9 inhibition	-	0.8355	83.55%
CYP2C19 inhibition	-	0.8115	81.15%
CYP2D6 inhibition	-	0.8420	84.20%
CYP1A2 inhibition	-	0.8318	83.18%
CYP2C8 inhibition	+	0.6799	67.99%
CYP inhibitory promiscuity	-	0.9333	93.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5449	54.49%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.7592	75.92%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5211	52.11%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	-	0.5011	50.11%
skin sensitisation	-	0.8380	83.80%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8606	86.06%
Acute Oral Toxicity (c)	III	0.5436	54.36%
Estrogen receptor binding	+	0.7845	78.45%
Androgen receptor binding	+	0.6524	65.24%
Thyroid receptor binding	+	0.5729	57.29%
Glucocorticoid receptor binding	+	0.6601	66.01%
Aromatase binding	+	0.6955	69.55%
PPAR gamma	+	0.6923	69.23%
Honey bee toxicity	-	0.6892	68.92%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8110	81.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.24%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.35%	99.23%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	94.87%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	94.56%	94.73%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.66%	89.34%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.16%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.43%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	90.85%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.12%	99.17%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	86.18%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.07%	96.90%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.89%	97.29%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.64%	96.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.02%	95.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.50%	82.50%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	83.35%	82.86%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.19%	98.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.15%	100.00%
CHEMBL1914	P06276	Butyrylcholinesterase	82.79%	95.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.80%	91.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.25%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	80.95%	90.17%
CHEMBL2535	P11166	Glucose transporter	80.13%	98.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.12%	94.33%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.02%	98.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 87642
• LOTUS: LTS0014571
• wikiData: Q407635