(E)-caffeoyl-CoA

Details

• Internal ID: 483d675e-2066-4be3-b333-1fb2ba58a6a0
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl thioesters > Enoyl CoAs > 2-enoyl CoAs
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[(3R)-4-[[3-[2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
• 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)/p-4/b6-4+/t19-,23-,24-,25+,29-/m1/s1
• InChI Key: QHRGJMIMHCLHRG-ZSELIEHESA-J
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈N₇O₁₉P₃S-₄
• Molecular Weight: 925.60 g/mol
• Exact Mass: 925.11560417 g/mol
• Topological Polar Surface Area (TPSA): 441.00 Ų
• XlogP: -4.60
• Atomic LogP (AlogP): -2.74
• H-Bond Acceptor: 25
• H-Bond Donor: 7
• Rotatable Bonds: 21

Synonyms

• trans-caffeoyl-CoA(4-)
• caffeoyl-CoA(4-)
• (E)-caffeoyl-CoA(4-)
• trans-caffeoyl-coenzyme A(4-)
• (E)-caffeoyl-coenzyme A(4-)
• CHEBI:57372
• CHEBI:87136
• (E)-3,4-dihydroxycinnamoyl-CoA(4-)
• trans-3,4-dihydroxycinnamoyl-CoA(4-)
• (E)-3,4-dihydroxycinnamoyl-coenzyme A(4-)
• trans-3,4-dihydroxycinnamoyl-coenzyme A(4-)
• Q27159393
• 3'-phosphonatoadenosine 5'-{3-[(3R)-4-{[3-({2-[(3,4-dihydroxyphenylprop-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] diphosphate}

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8828	88.28%
Caco-2	-	0.8594	85.94%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.3213	32.13%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.8664	86.64%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7849	78.49%
BSEP inhibitior	+	0.6882	68.82%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	+	0.7815	78.15%
CYP3A4 substrate	+	0.7179	71.79%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.7706	77.06%
CYP2C19 inhibition	-	0.7848	78.48%
CYP2D6 inhibition	-	0.8202	82.02%
CYP1A2 inhibition	-	0.8442	84.42%
CYP2C8 inhibition	+	0.8044	80.44%
CYP inhibitory promiscuity	-	0.8766	87.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5168	51.68%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.7585	75.85%
Skin corrosion	-	0.9194	91.94%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4097	40.97%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.5514	55.14%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.9389	93.89%
Acute Oral Toxicity (c)	III	0.5708	57.08%
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	-	0.6390	63.90%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9708	97.08%

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	99.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.23%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	96.96%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.95%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.69%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	96.26%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	95.42%	94.73%
CHEMBL1914	P06276	Butyrylcholinesterase	95.37%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.15%	89.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.11%	89.34%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	92.08%	96.90%
CHEMBL1951	P21397	Monoamine oxidase A	90.80%	91.49%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	90.48%	80.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.35%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.22%	90.71%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.18%	91.03%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.25%	80.78%
CHEMBL2535	P11166	Glucose transporter	83.34%	98.75%
CHEMBL1881	P43116	Prostanoid EP2 receptor	83.28%	93.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.26%	93.81%
CHEMBL4208	P20618	Proteasome component C5	82.40%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.83%	94.45%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	81.71%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.27%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.75%	97.09%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.13%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.00%	89.62%

Plants that contains it

• Boschniakia rossica

Cross-Links

• PubChem: 45266599
• NPASS: NPC169347