(1S,5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol

Details

• Internal ID: 8a993bf9-3622-496f-b596-94ef8f2ed721
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (1S,5R,6R,13R,21S)-5,13-bis(3,4-dihydroxyphenyl)-21-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19-tetrol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)OC7C(C(C(C(O7)CO)O)O)O)O)C8=CC(=C(C=C8)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC3=C2[C@H]4[C@@H]([C@@](O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)O)C8=CC(=C(C=C8)O)O)O
• InChI: InChI=1S/C36H34O17/c37-11-25-29(46)30(47)31(48)35(49-25)51-34-28-26-21(44)7-14(38)8-23(26)52-36(34,13-2-4-17(40)20(43)6-13)53-24-10-18(41)15-9-22(45)32(50-33(15)27(24)28)12-1-3-16(39)19(42)5-12/h1-8,10,22,25,28-32,34-35,37-48H,9,11H2/t22-,25-,28+,29+,30+,31-,32-,34+,35+,36-/m1/s1
• InChI Key: JUIIUJBWZYKSEP-DXNKJTEVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₄O₁₇
• Molecular Weight: 738.60 g/mol
• Exact Mass: 738.17959961 g/mol
• Topological Polar Surface Area (TPSA): 289.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 17
• H-Bond Donor: 12
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6717	67.17%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.5045	50.45%
OATP2B1 inhibitior	-	0.8480	84.80%
OATP1B1 inhibitior	+	0.8778	87.78%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8618	86.18%
P-glycoprotein inhibitior	+	0.6569	65.69%
P-glycoprotein substrate	-	0.6195	61.95%
CYP3A4 substrate	+	0.6768	67.68%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7754	77.54%
CYP3A4 inhibition	-	0.9314	93.14%
CYP2C9 inhibition	-	0.9322	93.22%
CYP2C19 inhibition	-	0.8611	86.11%
CYP2D6 inhibition	-	0.9200	92.00%
CYP1A2 inhibition	-	0.9301	93.01%
CYP2C8 inhibition	+	0.7712	77.12%
CYP inhibitory promiscuity	-	0.8859	88.59%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6438	64.38%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.8918	89.18%
Skin irritation	-	0.8032	80.32%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9049	90.49%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.8552	85.52%
skin sensitisation	-	0.9030	90.30%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6186	61.86%
Acute Oral Toxicity (c)	III	0.4801	48.01%
Estrogen receptor binding	+	0.8050	80.50%
Androgen receptor binding	+	0.7531	75.31%
Thyroid receptor binding	+	0.5875	58.75%
Glucocorticoid receptor binding	+	0.5488	54.88%
Aromatase binding	+	0.6228	62.28%
PPAR gamma	+	0.7538	75.38%
Honey bee toxicity	-	0.6542	65.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.6924	69.24%

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	99.91%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL233	P35372	Mu opioid receptor	96.97%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.96%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.21%	98.95%
CHEMBL236	P41143	Delta opioid receptor	92.61%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.71%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	90.40%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.24%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.07%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.94%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.25%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.49%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.59%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.36%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.77%	95.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.37%	97.36%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.16%	95.83%

Plants that contains it

• Aconitum liangshanicum
• Aconitum sachalinense
• Ageratina gracilis
• Alstonia deplanchei
• Asteriscus graveolens
• Baccharis megapotamica
• Centrosema pascuorum
• Ceratozamia fuscoviridis
• Citrus glauca
• Critonia quadrangularis
• Ficus simplicissima
• Flemingia macrophylla
• Gynura bicolor
• Haplophyllum dauricum
• Marrubium supinum
• Metalasia capitata
• Orthosphenia mexicana
• Oxyanthus speciosus
• Quercus dentata
• Rheum tanguticum
• Rhynchopsidium pumilum
• Senecio latifolius
• Senecio peripotamus
• Solanum elaeagnifolium
• Stevia mercedensis
• Strychnos tabascana
• Styrax hookeri
• Swinglea glutinosa
• Theobroma cacao
• Thuja standishii
• Verbesina rupestris

Cross-Links

• PubChem: 118731401
• NPASS: NPC185231