2'',4''-Di-O-(E-p-Coumaroyl)afzelin

Details

• Internal ID: 5a6d0764-af15-4f41-afad-e5ca5bbf91c6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4R,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)C=CC5=CC=C(C=C5)O)O)OC(=O)C=CC6=CC=C(C=C6)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)OC(=O)/C=C/C5=CC=C(C=C5)O)O)OC(=O)/C=C/C6=CC=C(C=C6)O
• InChI: InChI=1S/C39H32O14/c1-20-35(51-30(45)16-6-21-2-10-24(40)11-3-21)34(48)38(52-31(46)17-7-22-4-12-25(41)13-5-22)39(49-20)53-37-33(47)32-28(44)18-27(43)19-29(32)50-36(37)23-8-14-26(42)15-9-23/h2-20,34-35,38-44,48H,1H3/b16-6+,17-7+/t20-,34+,35-,38+,39-/m0/s1
• InChI Key: KMOHJUXDKSMQOG-NCLAQALISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₂O₁₄
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.17920569 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.72
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• 2'',4''-Di-O-(E-p-Coumaroyl)afzelin
• 2/,4/-Di-O-(E-p-couMaroyl)afzelin
• CHEMBL1642586
• [(2S,3R,4R,5R,6S)-6-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• KMOHJUXDKSMQOG-NCLAQALISA-N
• HY-N1669
• BDBM50334671
• 2',4'-Di-O-(E-p-coumaroyl)afzelin
• AKOS040760982
• CS-0017331
• kaempferol-3-O-alpha-L-(2'''', 4''''-di-E-p-coumaroyl)-rhamnoside
• 3-[2-O,4-O-Bis(4-hydroxy-trans-cinnamoyl)-alpha-L-rhamnopyranosyloxy]-5,7,4'-trihydroxyflavone
• 4H-1-Benzopyran-4-one, 3-[[6-deoxy-2,4-bis-O-[(2Z)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]--L-mannopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9132	91.32%
Caco-2	-	0.8691	86.91%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6553	65.53%
OATP2B1 inhibitior	-	0.7040	70.40%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8362	83.62%
P-glycoprotein inhibitior	+	0.7970	79.70%
P-glycoprotein substrate	+	0.5356	53.56%
CYP3A4 substrate	+	0.6691	66.91%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.6871	68.71%
CYP2C9 inhibition	+	0.7123	71.23%
CYP2C19 inhibition	-	0.6079	60.79%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.8259	82.59%
CYP2C8 inhibition	+	0.8997	89.97%
CYP inhibitory promiscuity	+	0.5931	59.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4497	44.97%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8901	89.01%
Skin irritation	-	0.6486	64.86%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.5274	52.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4248	42.48%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8652	86.52%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.9135	91.35%
Acute Oral Toxicity (c)	III	0.5519	55.19%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.8045	80.45%
Thyroid receptor binding	+	0.5654	56.54%
Glucocorticoid receptor binding	+	0.7087	70.87%
Aromatase binding	-	0.6107	61.07%
PPAR gamma	+	0.6727	67.27%
Honey bee toxicity	-	0.7680	76.80%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9816	98.16%

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	99.17%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.02%	89.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	98.32%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.35%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.79%	91.49%
CHEMBL3194	P02766	Transthyretin	95.92%	90.71%
CHEMBL2581	P07339	Cathepsin D	95.77%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.38%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	90.87%	98.35%
CHEMBL3401	O75469	Pregnane X receptor	89.63%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.12%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.48%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.08%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.98%	93.99%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.66%	95.78%
CHEMBL4208	P20618	Proteasome component C5	85.23%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.99%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.32%	99.23%
CHEMBL4530	P00488	Coagulation factor XIII	82.73%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.70%	94.45%
CHEMBL3959	P16083	Quinone reductase 2	82.61%	89.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.22%	95.89%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.94%	88.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.83%	96.12%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.71%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.87%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.79%	99.15%

Plants that contains it

• Abies nephrolepis
• Acer carpinifolium
• Cinnamomum kotoense
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium sagittatum
• Eriobotrya japonica
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hornstedtia reticulata
• Hypericum revolutum
• Laurus nobilis
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Osmorhiza aristata
• Pentachondra pumila
• Psychotria serpens
• Pycnandra acuminata
• Stipa robusta
• Succisa pratensis

Cross-Links

• PubChem: 11765457
• NPASS: NPC221288
• LOTUS: LTS0049869
• wikiData: Q105143074