Caffeoyl-coa

Details

• Internal ID: e4def8f1-423e-402f-acfd-412436b92140
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl thioesters > Enoyl CoAs > 2-enoyl CoAs
• IUPAC Name: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enethioate
• SMILES (Canonical): CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)C=CC4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSC(=O)/C=C/C4=CC(=C(C=C4)O)O)O
• InChI: InChI=1S/C30H42N7O19P3S/c1-30(2,25(43)28(44)33-8-7-20(40)32-9-10-60-21(41)6-4-16-3-5-17(38)18(39)11-16)13-53-59(50,51)56-58(48,49)52-12-19-24(55-57(45,46)47)23(42)29(54-19)37-15-36-22-26(31)34-14-35-27(22)37/h3-6,11,14-15,19,23-25,29,38-39,42-43H,7-10,12-13H2,1-2H3,(H,32,40)(H,33,44)(H,48,49)(H,50,51)(H2,31,34,35)(H2,45,46,47)/b6-4+/t19-,23-,24-,25+,29-/m1/s1
• InChI Key: QHRGJMIMHCLHRG-ZSELIEHESA-N
• Popularity: 28 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂N₇O₁₉P₃S
• Molecular Weight: 929.70 g/mol
• Exact Mass: 929.14690430 g/mol
• Topological Polar Surface Area (TPSA): 429.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 21

Synonyms

• trans-caffeoyl-CoA
• 3,4-dihydroxyacryloyl-CoA
• 1021913-49-4
• 3'-phosphoadenosine 5'-{3-[(3R)-4-{[3-({2-[(3,4-dihydroxyphenylprop-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
• Caffeoyl-Coenzym A
• trans-caffeoyl-coenzyme A
• (E)-caffeoyl-coenzyme A
• CHEBI:15518
• CHEBI:87449
• (E)-3,4-dihydroxycinnamoyl-CoA
• 3,4-dihydroxyacryloyl-Coenzyme A
• QHRGJMIMHCLHRG-ZSELIEHESA-N
• trans-3,4-dihydroxycinnamoyl-CoA
• DTXSID501195067
• HY-N9686
• LMFA07050293
• (E)-3,4-dihydroxycinnamoyl-coenzyme A
• trans-3,4-dihydroxycinnamoyl-coenzyme A
• CS-0202829
• C00323
• (2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl-CoA
• Q27159631
• Coenzyme A, S-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• 3'-phosphoadenosine 5'-{3-[(3R)-4-{[3-({2-[(2E)-(3,4-dihydroxyphenylprop-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
• S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enethioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9258	92.58%
Caco-2	-	0.8594	85.94%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4121	41.21%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.9337	93.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8099	80.99%
BSEP inhibitior	+	0.6882	68.82%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.7913	79.13%
CYP3A4 substrate	+	0.7170	71.70%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8615	86.15%
CYP3A4 inhibition	+	0.5398	53.98%
CYP2C9 inhibition	-	0.7425	74.25%
CYP2C19 inhibition	-	0.7633	76.33%
CYP2D6 inhibition	-	0.8282	82.82%
CYP1A2 inhibition	-	0.8200	82.00%
CYP2C8 inhibition	+	0.8118	81.18%
CYP inhibitory promiscuity	-	0.8265	82.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5375	53.75%
Eye corrosion	-	0.9808	98.08%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.7584	75.84%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4097	40.97%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	-	0.5889	58.89%
skin sensitisation	-	0.8378	83.78%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9142	91.42%
Acute Oral Toxicity (c)	III	0.5637	56.37%
Estrogen receptor binding	+	0.7746	77.46%
Androgen receptor binding	+	0.7479	74.79%
Thyroid receptor binding	+	0.6121	61.21%
Glucocorticoid receptor binding	+	0.6550	65.50%
Aromatase binding	+	0.6677	66.77%
PPAR gamma	+	0.7487	74.87%
Honey bee toxicity	-	0.6352	63.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9696	96.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.42%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.03%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.55%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	96.35%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.29%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.28%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.20%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	96.13%	93.10%
CHEMBL1914	P06276	Butyrylcholinesterase	95.88%	95.00%
CHEMBL3401	O75469	Pregnane X receptor	95.73%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.38%	99.23%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.16%	89.34%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	93.81%	80.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	93.55%	91.03%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	88.28%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.27%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.61%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.24%	95.89%
CHEMBL2535	P11166	Glucose transporter	84.76%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.24%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	83.97%	95.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.98%	89.62%
CHEMBL4208	P20618	Proteasome component C5	81.66%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.53%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.02%	80.78%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.83%	100.00%
CHEMBL1881	P43116	Prostanoid EP2 receptor	80.23%	93.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.14%	90.17%

Plants that contains it

• Aglaia rubiginosa
• Arabidopsis thaliana
• Quercus robur

Cross-Links

• PubChem: 11966126
• LOTUS: LTS0129785
• wikiData: Q105254032