3'',4''-Di-O-p-coumaroylafzelin

Details

• Internal ID: f5d9c4d3-eba4-4f08-9a38-9804fca730fd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(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)O)OC(=O)C=CC5=CC=C(C=C5)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)O)OC(=O)/C=C/C5=CC=C(C=C5)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)38(52-31(46)17-7-22-4-12-25(41)13-5-22)34(48)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: RMHWAEFAOBGGBH-GLRBGJJXSA-N
• Popularity: 0 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

• 166321-99-9
• [(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 2-(4-Hydroxyphenyl)-5,7-dihydroxy-3-[3-O,4-O-bis[3-(4-hydroxyphenyl)acryloyl]-alpha-L-rhamnopyranosyloxy]-4H-1-benzopyran-4-one
• 3-[3-O,4-O-Bis(4-hydroxy-trans-cinnamoyl)-alpha-L-rhamnopyranosyloxy]-5,7,4'-trihydroxyflavone
• NCGC00385628-01![(2S,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9132	91.32%
Caco-2	-	0.8676	86.76%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6553	65.53%
OATP2B1 inhibitior	-	0.5664	56.64%
OATP1B1 inhibitior	+	0.8535	85.35%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8319	83.19%
P-glycoprotein inhibitior	+	0.7849	78.49%
P-glycoprotein substrate	+	0.5353	53.53%
CYP3A4 substrate	+	0.6717	67.17%
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	+	0.8912	89.12%
CYP inhibitory promiscuity	+	0.5931	59.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.4497	44.97%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8905	89.05%
Skin irritation	-	0.6486	64.86%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.5174	51.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.5149	51.49%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8652	86.52%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8993	89.93%
Acute Oral Toxicity (c)	III	0.5519	55.19%
Estrogen receptor binding	+	0.7646	76.46%
Androgen receptor binding	+	0.8192	81.92%
Thyroid receptor binding	+	0.5875	58.75%
Glucocorticoid receptor binding	+	0.7452	74.52%
Aromatase binding	-	0.5593	55.93%
PPAR gamma	+	0.6588	65.88%
Honey bee toxicity	-	0.7532	75.32%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	99.25%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.05%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.36%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.06%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.39%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.72%	95.64%
CHEMBL3194	P02766	Transthyretin	95.53%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.38%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.37%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.16%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	88.98%	98.35%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.08%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.92%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.66%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.26%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.72%	93.99%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.22%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.00%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.99%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.96%	90.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.62%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.51%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.94%	90.71%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.78%	88.00%

Plants that contains it

• Acer carpinifolium
• 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
• Psychotria serpens
• Pycnandra acuminata
• Stipa robusta
• Succisa pratensis

Cross-Links

• PubChem: 51136469
• NPASS: NPC72406
• LOTUS: LTS0152781
• wikiData: Q105240783