[(1S,2S,4S,5R,6S,7R,8S,9S,12R)-4,5-diacetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-8-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate

Details

• Internal ID: ce1b8aaf-9142-4b3a-b90a-19efd77825cf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
• IUPAC Name: [(1S,2S,4S,5R,6S,7R,8S,9S,12R)-4,5-diacetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-8-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-7-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC(C23C(C(C(C(C2(C1OC(=O)C)C)OC(=O)C4=CC=CC=C4)OC(=O)C=CC5=CC=CC=C5)C(O3)(C)C)O)(C)O
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@]([C@@]23[C@@H]([C@@H]([C@@H]([C@@H]([C@@]2([C@H]1OC(=O)C)C)OC(=O)C4=CC=CC=C4)OC(=O)/C=C/C5=CC=CC=C5)C(O3)(C)C)O)(C)O
• InChI: InChI=1S/C35H40O11/c1-20(36)42-24-19-33(5,41)35-28(39)26(32(3,4)46-35)27(44-25(38)18-17-22-13-9-7-10-14-22)30(34(35,6)29(24)43-21(2)37)45-31(40)23-15-11-8-12-16-23/h7-18,24,26-30,39,41H,19H2,1-6H3/b18-17+/t24-,26+,27-,28+,29-,30-,33-,34-,35-/m0/s1
• InChI Key: RKQBXPZSTLHXPR-XFOFPURASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₀O₁₁
• Molecular Weight: 636.70 g/mol
• Exact Mass: 636.25706209 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• BDBM50088576

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9321	93.21%
Caco-2	-	0.8103	81.03%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5095	50.95%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8538	85.38%
OATP1B3 inhibitior	+	0.9111	91.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9749	97.49%
P-glycoprotein inhibitior	+	0.8986	89.86%
P-glycoprotein substrate	-	0.5490	54.90%
CYP3A4 substrate	+	0.6790	67.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8778	87.78%
CYP3A4 inhibition	+	0.5526	55.26%
CYP2C9 inhibition	-	0.7928	79.28%
CYP2C19 inhibition	-	0.8553	85.53%
CYP2D6 inhibition	-	0.9150	91.50%
CYP1A2 inhibition	-	0.8503	85.03%
CYP2C8 inhibition	+	0.7879	78.79%
CYP inhibitory promiscuity	-	0.7156	71.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4158	41.58%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8930	89.30%
Skin irritation	-	0.7302	73.02%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7925	79.25%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.7291	72.91%
skin sensitisation	-	0.7740	77.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6856	68.56%
Acute Oral Toxicity (c)	I	0.3681	36.81%
Estrogen receptor binding	+	0.7731	77.31%
Androgen receptor binding	+	0.7185	71.85%
Thyroid receptor binding	+	0.6670	66.70%
Glucocorticoid receptor binding	+	0.6854	68.54%
Aromatase binding	+	0.5887	58.87%
PPAR gamma	+	0.7455	74.55%
Honey bee toxicity	-	0.7586	75.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5445	54.45%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	420 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.20%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.39%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.19%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.83%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	93.17%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	89.25%	81.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.10%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.60%	96.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.23%	83.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.47%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.42%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL5028	O14672	ADAM10	85.56%	97.50%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.19%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.15%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.78%	93.99%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.90%	89.44%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.25%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.97%	91.07%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.57%	87.67%
CHEMBL340	P08684	Cytochrome P450 3A4	80.56%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.05%	95.89%

Plants that contains it

• Dryopteris crassirhizoma

Cross-Links

• PubChem: 122177555
• LOTUS: LTS0164695
• wikiData: Q105301326