(1S,8S,9S,16S)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaene-4,6,9,12-tetrol

Details

• Internal ID: 6f3f9b17-84a2-4367-91c6-0c1eda356952
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (1S,8S,9S,16S)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.02,7.014,17]heptadeca-2(7),3,5,10(17),11,13-hexaene-4,6,9,12-tetrol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C4C(C(OC4=CC(=C3)O)C5=CC=C(C=C5)O)C6=C2C(=CC(=C6)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@@H](C3=C4[C@@H]([C@H](OC4=CC(=C3)O)C5=CC=C(C=C5)O)C6=C2C(=CC(=C6)O)O)O)O
• InChI: InChI=1S/C28H22O7/c29-15-5-1-13(2-6-15)23-24-19(9-17(31)11-21(24)33)26-25-20(27(23)34)10-18(32)12-22(25)35-28(26)14-3-7-16(30)8-4-14/h1-12,23,26-34H/t23-,26-,27+,28+/m0/s1
• InChI Key: LHUHHURKGTUZHU-DXXRHUJXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₂O₇
• Molecular Weight: 470.50 g/mol
• Exact Mass: 470.13655304 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 7
• 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	+	0.9827	98.27%
Caco-2	-	0.9024	90.24%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	+	0.5721	57.21%
OATP1B1 inhibitior	+	0.7423	74.23%
OATP1B3 inhibitior	-	0.3378	33.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7389	73.89%
P-glycoprotein inhibitior	-	0.5548	55.48%
P-glycoprotein substrate	-	0.8990	89.90%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	+	0.6031	60.31%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	+	0.5280	52.80%
CYP2C9 inhibition	+	0.8315	83.15%
CYP2C19 inhibition	+	0.8416	84.16%
CYP2D6 inhibition	-	0.8469	84.69%
CYP1A2 inhibition	+	0.8607	86.07%
CYP2C8 inhibition	+	0.6539	65.39%
CYP inhibitory promiscuity	+	0.9212	92.12%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4584	45.84%
Eye corrosion	-	0.9889	98.89%
Eye irritation	+	0.6633	66.33%
Skin irritation	+	0.5289	52.89%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6790	67.90%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8034	80.34%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.6155	61.55%
Acute Oral Toxicity (c)	III	0.4139	41.39%
Estrogen receptor binding	+	0.6488	64.88%
Androgen receptor binding	+	0.7777	77.77%
Thyroid receptor binding	+	0.7338	73.38%
Glucocorticoid receptor binding	+	0.6540	65.40%
Aromatase binding	+	0.6507	65.07%
PPAR gamma	+	0.7788	77.88%
Honey bee toxicity	-	0.8470	84.70%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9646	96.46%

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	97.58%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.98%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.15%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.02%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.61%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.77%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.76%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.78%	95.56%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.41%	97.33%
CHEMBL1951	P21397	Monoamine oxidase A	80.13%	91.49%

Plants that contains it

• Hopea jucunda
• Hopea malibato

Cross-Links

• PubChem: 159354832
• LOTUS: LTS0002292
• wikiData: Q105151971