(2S,2'R,3'S,8'S)-3',4,5',6-tetrahydroxy-2',8'-bis(4-hydroxyphenyl)spiro[1-benzofuran-2,9'-2,3,4,8-tetrahydrofuro[2,3-h]chromene]-3-one

Details

• Internal ID: fe627f1a-a432-434e-91f6-7eba0ca0bb5d
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,2'R,3'S,8'S)-3',4,5',6-tetrahydroxy-2',8'-bis(4-hydroxyphenyl)spiro[1-benzofuran-2,9'-2,3,4,8-tetrahydrofuro[2,3-h]chromene]-3-one
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C4(C(O3)C5=CC=C(C=C5)O)C(=O)C6=C(C=C(C=C6O4)O)O)O)C7=CC=C(C=C7)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2[C@]4([C@@H](O3)C5=CC=C(C=C5)O)C(=O)C6=C(C=C(C=C6O4)O)O)O)C7=CC=C(C=C7)O)O
• InChI: InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)26-21(36)11-18-19(34)12-23-25(27(18)39-26)30(29(38-23)14-3-7-16(32)8-4-14)28(37)24-20(35)9-17(33)10-22(24)40-30/h1-10,12,21,26,29,31-36H,11H2/t21-,26+,29-,30+/m0/s1
• InChI Key: BYBKYSAHKVMKNH-UDJVMPNMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₁₀
• Molecular Weight: 542.50 g/mol
• Exact Mass: 542.12129689 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.86
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.8936	89.36%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6992	69.92%
OATP2B1 inhibitior	-	0.5690	56.90%
OATP1B1 inhibitior	+	0.6918	69.18%
OATP1B3 inhibitior	-	0.3299	32.99%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8931	89.31%
P-glycoprotein inhibitior	+	0.7685	76.85%
P-glycoprotein substrate	-	0.6559	65.59%
CYP3A4 substrate	+	0.6382	63.82%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.7268	72.68%
CYP3A4 inhibition	+	0.5107	51.07%
CYP2C9 inhibition	-	0.6170	61.70%
CYP2C19 inhibition	-	0.7493	74.93%
CYP2D6 inhibition	-	0.8796	87.96%
CYP1A2 inhibition	-	0.8579	85.79%
CYP2C8 inhibition	+	0.6470	64.70%
CYP inhibitory promiscuity	-	0.7486	74.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4733	47.33%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.7640	76.40%
Skin irritation	-	0.6404	64.04%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6978	69.78%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7008	70.08%
Acute Oral Toxicity (c)	III	0.4179	41.79%
Estrogen receptor binding	+	0.8062	80.62%
Androgen receptor binding	+	0.7711	77.11%
Thyroid receptor binding	+	0.6089	60.89%
Glucocorticoid receptor binding	+	0.7281	72.81%
Aromatase binding	-	0.4917	49.17%
PPAR gamma	+	0.7226	72.26%
Honey bee toxicity	-	0.7233	72.33%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.7682	76.82%

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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.40%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.19%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.64%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.31%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.04%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.63%	93.40%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.45%	85.11%
CHEMBL236	P41143	Delta opioid receptor	88.69%	99.35%
CHEMBL3401	O75469	Pregnane X receptor	88.20%	94.73%
CHEMBL2535	P11166	Glucose transporter	88.17%	98.75%
CHEMBL4040	P28482	MAP kinase ERK2	86.56%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.30%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.22%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.38%	95.89%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	82.19%	95.55%
CHEMBL3194	P02766	Transthyretin	81.82%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.10%	96.12%
CHEMBL233	P35372	Mu opioid receptor	80.50%	97.93%

Plants that contains it

• Acer caudatifolium
• Aconitum heterophyllum
• Astragalus sinicus
• Baccharis macraei
• Cynoglossum lanceolatum
• Daphne feddei
• Daphne odora
• Klasea centauroides subsp. strangulata
• Leucoptera nodosa
• Lindera glauca
• Marshallia graminifolia
• Mikania goyazensis
• Oxytropis ochrocephala
• Rumohra adiantiformis
• Salacia cordata
• Solanum aculeatissimum
• Stenocephalum megapotamicum
• Syzygium sandwicense

Cross-Links

• PubChem: 100885566
• NPASS: NPC68011
• LOTUS: LTS0108961
• wikiData: Q104949115