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

Details

• Internal ID: b8713fc9-2ec0-4562-bc2b-50f9ce3c31be
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/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: FBSKJMQYURKNSU-RGPIVSQRSA-N
• Popularity: 0 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: -0.50
• Atomic LogP (AlogP): -1.02
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• SCHEMBL18826154
• AKOS015965213
• AC-6026

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7586	75.86%
Caco-2	-	0.9049	90.49%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7962	79.62%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8832	88.32%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8204	82.04%
P-glycoprotein inhibitior	-	0.5537	55.37%
P-glycoprotein substrate	-	0.6291	62.91%
CYP3A4 substrate	+	0.6492	64.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8907	89.07%
CYP2C9 inhibition	-	0.7325	73.25%
CYP2C19 inhibition	-	0.8467	84.67%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.8483	84.83%
CYP2C8 inhibition	+	0.6859	68.59%
CYP inhibitory promiscuity	-	0.5836	58.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6709	67.09%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.8374	83.74%
Skin corrosion	-	0.9574	95.74%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7157	71.57%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8149	81.49%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.9493	94.93%
Acute Oral Toxicity (c)	III	0.8034	80.34%
Estrogen receptor binding	+	0.7890	78.90%
Androgen receptor binding	-	0.6862	68.62%
Thyroid receptor binding	+	0.5677	56.77%
Glucocorticoid receptor binding	+	0.5647	56.47%
Aromatase binding	-	0.4847	48.47%
PPAR gamma	+	0.6924	69.24%
Honey bee toxicity	-	0.6626	66.26%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7773	77.73%

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	99.72%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.25%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.58%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.60%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	92.96%	94.73%
CHEMBL3194	P02766	Transthyretin	92.79%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.61%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.28%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.89%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.85%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.02%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.36%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.61%	96.37%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.15%	91.71%

Plants that contains it

• Brandisia hancei
• Buddleja officinalis
• Campsis grandiflora
• Cistanche deserticola
• Cistanche phelypaea
• Clerodendrum trichotomum
• Fraxinus ornus
• Lantana camara
• Paulownia tomentosa
• Phlomoides rotata
• Plantago asiatica
• Plantago major
• Rehmannia glutinosa

Cross-Links

• PubChem: 45358104
• NPASS: NPC114705