coumaroyl(-1)[coumaroyl(3-OMe)(-6)]Fruf(b2-1a)Glc

Details

• Internal ID: a1d90db6-f90f-4368-b7bd-a1786abffb8d
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4S,5R)-3,4-dihydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(O2)(COC(=O)C=CC3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@](O2)(COC(=O)/C=C/C3=CC=C(C=C3)O)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C31H36O16/c1-42-20-12-17(4-9-19(20)34)6-11-23(35)43-14-22-26(38)29(41)31(46-22,47-30-28(40)27(39)25(37)21(13-32)45-30)15-44-24(36)10-5-16-2-7-18(33)8-3-16/h2-12,21-22,25-30,32-34,37-41H,13-15H2,1H3/b10-5+,11-6+/t21-,22-,25-,26-,27+,28-,29+,30-,31+/m1/s1
• InChI Key: ZKMBADUFQINEPA-VUFRXCLUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₆O₁₆
• Molecular Weight: 664.60 g/mol
• Exact Mass: 664.20033506 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7896	78.96%
Caco-2	-	0.9019	90.19%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7330	73.30%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8486	84.86%
OATP1B3 inhibitior	+	0.9647	96.47%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8881	88.81%
P-glycoprotein inhibitior	+	0.5967	59.67%
P-glycoprotein substrate	-	0.6800	68.00%
CYP3A4 substrate	+	0.6585	65.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	-	0.8175	81.75%
CYP2C9 inhibition	-	0.8078	80.78%
CYP2C19 inhibition	-	0.7609	76.09%
CYP2D6 inhibition	-	0.9190	91.90%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	+	0.8043	80.43%
CYP inhibitory promiscuity	-	0.7424	74.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6241	62.41%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.8494	84.94%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7609	76.09%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8167	81.67%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8570	85.70%
Acute Oral Toxicity (c)	III	0.6819	68.19%
Estrogen receptor binding	+	0.8456	84.56%
Androgen receptor binding	+	0.6843	68.43%
Thyroid receptor binding	+	0.5385	53.85%
Glucocorticoid receptor binding	+	0.6469	64.69%
Aromatase binding	+	0.5644	56.44%
PPAR gamma	+	0.7348	73.48%
Honey bee toxicity	-	0.7241	72.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9224	92.24%

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	99.55%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.60%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.70%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.40%	89.00%
CHEMBL3194	P02766	Transthyretin	92.78%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.12%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.81%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.38%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.81%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.09%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.95%	89.67%
CHEMBL1951	P21397	Monoamine oxidase A	86.50%	91.49%
CHEMBL4208	P20618	Proteasome component C5	83.65%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.53%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.42%	95.89%

Plants that contains it

• Ageratina adenophora
• Boehmeria nivea
• Crotalaria micans
• Croton poilanei
• Dasymaschalon sootepense
• Dictyoloma vandellianum
• Euonymus sachalinensis
• Felicia erigeroides
• Flueggea virosa subsp. melanthesoides
• Guatteria megalophylla
• Lupinus paniculatus
• Lycoris traubii
• Lygodium flexuosum
• Panax ginseng
• Saccharum spontaneum
• Smilax bracteata
• Strychnos staudtii
• Tsuga mertensiana

Cross-Links

• PubChem: 11735009
• NPASS: NPC16841
• LOTUS: LTS0093524
• wikiData: Q105378578