1-[11-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-oxa-8-oxoniatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-3-yl]ethanone

Details

• Internal ID: d877d2f8-4b4f-42de-9f8d-b6a5128e3b64
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: 1-[11-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-oxa-8-oxoniatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-3-yl]ethanone
• SMILES (Canonical): CC(=O)C1=CC2=C(C(=[O+]C3=C2C(=CC(=C3)O)O1)C4=CC(=C(C(=C4)OC)O)OC)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): CC(=O)C1=CC2=C(C(=[O+]C3=C2C(=CC(=C3)O)O1)C4=CC(=C(C(=C4)OC)O)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H26O13/c1-10(29)14-8-13-20-15(37-14)6-12(30)7-16(20)38-25(11-4-17(35-2)21(31)18(5-11)36-3)26(13)40-27-24(34)23(33)22(32)19(9-28)39-27/h4-8,19,22-24,27-28,32-34H,9H2,1-3H3,(H-,30,31)/p+1/t19-,22-,23+,24-,27+/m1/s1
• InChI Key: JWAHHFJXIOBPJA-WBYCZGBQSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₇O₁₃+
• Molecular Weight: 559.50 g/mol
• Exact Mass: 559.14516591 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7614	76.14%
Caco-2	-	0.8568	85.68%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4726	47.26%
OATP2B1 inhibitior	-	0.7059	70.59%
OATP1B1 inhibitior	+	0.8560	85.60%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8467	84.67%
P-glycoprotein inhibitior	+	0.5811	58.11%
P-glycoprotein substrate	+	0.5658	56.58%
CYP3A4 substrate	+	0.6574	65.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8506	85.06%
CYP3A4 inhibition	-	0.9417	94.17%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.8436	84.36%
CYP2D6 inhibition	-	0.9066	90.66%
CYP1A2 inhibition	-	0.8593	85.93%
CYP2C8 inhibition	+	0.8150	81.50%
CYP inhibitory promiscuity	-	0.6314	63.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6730	67.30%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.8330	83.30%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6499	64.99%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6820	68.20%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9328	93.28%
Acute Oral Toxicity (c)	III	0.5668	56.68%
Estrogen receptor binding	+	0.8551	85.51%
Androgen receptor binding	+	0.6711	67.11%
Thyroid receptor binding	+	0.5333	53.33%
Glucocorticoid receptor binding	+	0.8153	81.53%
Aromatase binding	+	0.5347	53.47%
PPAR gamma	+	0.6767	67.67%
Honey bee toxicity	-	0.6944	69.44%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	+	0.7625	76.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.78%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.79%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.41%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.62%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.45%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.51%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.33%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.23%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.11%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.97%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.76%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.81%	96.95%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.50%	97.88%
CHEMBL220	P22303	Acetylcholinesterase	84.41%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.39%	96.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.24%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.73%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.62%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.60%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.10%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.52%	92.94%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 102313791
• NPASS: NPC50364