[(2R,3R,4R,5R,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: cd6817a6-ab99-49f9-b951-e88bf08d108e
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OCCC3=CC(=C(C=C3)O)O)CO)O)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@@H]([C@@H]([C@H](O[C@H]2OCCC3=CC(=C(C=C3)O)O)CO)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(36)24(38)25(39)28(41-13)44-27-26(43-21(35)7-4-14-2-5-16(31)18(33)10-14)23(37)20(12-30)42-29(27)40-9-8-15-3-6-17(32)19(34)11-15/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28-,29+/m0/s1
• InChI Key: QLZWUGOYBODRLF-QQLYGORSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7512	75.12%
Caco-2	-	0.9013	90.13%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8655	86.55%
P-glycoprotein inhibitior	-	0.5065	50.65%
P-glycoprotein substrate	-	0.6313	63.13%
CYP3A4 substrate	+	0.6464	64.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.7548	75.48%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.7033	70.33%
CYP inhibitory promiscuity	-	0.7002	70.02%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6737	67.37%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9214	92.14%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8486	84.86%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9461	94.61%
Acute Oral Toxicity (c)	III	0.7702	77.02%
Estrogen receptor binding	+	0.7910	79.10%
Androgen receptor binding	-	0.6991	69.91%
Thyroid receptor binding	+	0.5838	58.38%
Glucocorticoid receptor binding	+	0.5680	56.80%
Aromatase binding	-	0.4855	48.55%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.6847	68.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7970	79.70%

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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.35%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.10%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.61%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.73%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	93.40%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.02%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.01%	86.92%
CHEMBL3194	P02766	Transthyretin	92.01%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.35%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.17%	96.37%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.08%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.84%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.40%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.93%	90.00%

Plants that contains it

• Alpinia flabellata
• Angelica japonica
• Baccharis truncata
• Benincasa hispida
• Centaurea benedicta
• Chloranthus fortunei
• Chuquiraga erinacea
• Cuphea hyssopifolia
• Cylindrolobus mucronatus
• Euphorbia palustris
• Euphorbia pithyusa
• Farfugium japonicum
• Fouquieria diguetii
• Fritillaria monantha
• Holarrhena floribunda
• Lathyrus latifolius
• Magnolia obovata
• Magnolia officinalis
• Ononis viscosa
• Paragynoxys meridana
• Pedicularis rex
• Pinus edulis
• Posidonia oceanica
• Pterocarpus erinaceus
• Pyrus bourgaeana
• Salvia broussonetii
• Sandoricum koetjape
• Sedum sarmentosum
• Sorbus torminalis
• Suaeda maritima
• Triunia erythrocarpa

Cross-Links

• PubChem: 21629882
• NPASS: NPC81239
• LOTUS: LTS0148530
• wikiData: Q105223862