(8S)-3,8-dihydroxy-16,17-dimethoxy-15-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one

Details

• Internal ID: d65dfc6a-3bb2-477c-9410-52a7deedca2b
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Cyclic diarylheptanoids > Meta,meta-bridged biphenyls
• IUPAC Name: (8S)-3,8-dihydroxy-16,17-dimethoxy-15-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
• SMILES (Canonical): COC1=C2C=C(CCCCC(=O)C(CC3=CC2=C(C=C3)O)O)C(=C1OC)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C2C=C(CCCCC(=O)[C@H](CC3=CC2=C(C=C3)O)O)C(=C1OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C27H34O11/c1-35-25-16-11-14(5-3-4-6-18(30)19(31)10-13-7-8-17(29)15(16)9-13)24(26(25)36-2)38-27-23(34)22(33)21(32)20(12-28)37-27/h7-9,11,19-23,27-29,31-34H,3-6,10,12H2,1-2H3/t19-,20+,21+,22-,23+,27-/m0/s1
• InChI Key: BSILZSYJTIBPFN-HDUIEKHKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₁
• Molecular Weight: 534.60 g/mol
• Exact Mass: 534.21011190 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.45
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5816	58.16%
Caco-2	-	0.8354	83.54%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6993	69.93%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8802	88.02%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8042	80.42%
BSEP inhibitior	+	0.9493	94.93%
P-glycoprotein inhibitior	-	0.5616	56.16%
P-glycoprotein substrate	-	0.6596	65.96%
CYP3A4 substrate	+	0.6284	62.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.7928	79.28%
CYP2C9 inhibition	-	0.9322	93.22%
CYP2C19 inhibition	-	0.8210	82.10%
CYP2D6 inhibition	-	0.8262	82.62%
CYP1A2 inhibition	-	0.5493	54.93%
CYP2C8 inhibition	+	0.4445	44.45%
CYP inhibitory promiscuity	-	0.9038	90.38%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7863	78.63%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.8241	82.41%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7074	70.74%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8517	85.17%
Acute Oral Toxicity (c)	III	0.6809	68.09%
Estrogen receptor binding	+	0.8172	81.72%
Androgen receptor binding	+	0.5702	57.02%
Thyroid receptor binding	-	0.5246	52.46%
Glucocorticoid receptor binding	+	0.6448	64.48%
Aromatase binding	+	0.5614	56.14%
PPAR gamma	+	0.7062	70.62%
Honey bee toxicity	-	0.8219	82.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8388	83.88%

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	99.58%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.00%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.23%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.84%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.78%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.70%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.24%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.62%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.75%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.47%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.52%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.09%	90.71%
CHEMBL2535	P11166	Glucose transporter	82.18%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.04%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.60%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.33%	94.45%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.18%	95.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.01%	100.00%

Plants that contains it

• Myrica gale

Cross-Links

• PubChem: 162985690
• LOTUS: LTS0171137
• wikiData: Q104945257