[(1S,2S,5S,6S,7S,8S,9R,12R)-7-acetyloxy-6-(acetyloxymethyl)-2,8,12-trihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] benzoate

Details

• Internal ID: 09fc1cae-005c-4dcb-92d6-9952ade3b43c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Agarofurans
• IUPAC Name: [(1S,2S,5S,6S,7S,8S,9R,12R)-7-acetyloxy-6-(acetyloxymethyl)-2,8,12-trihydroxy-2,10,10-trimethyl-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] benzoate
• SMILES (Canonical): CC(=O)OCC12C(CCC(C13C(C(C(C2OC(=O)C)O)C(O3)(C)C)O)(C)O)OC(=O)C4=CC=CC=C4
• SMILES (Isomeric): CC(=O)OC[C@@]12[C@H](CC[C@]([C@@]13[C@@H]([C@@H]([C@@H]([C@H]2OC(=O)C)O)C(O3)(C)C)O)(C)O)OC(=O)C4=CC=CC=C4
• InChI: InChI=1S/C26H34O10/c1-14(27)33-13-25-17(35-22(31)16-9-7-6-8-10-16)11-12-24(5,32)26(25)20(30)18(23(3,4)36-26)19(29)21(25)34-15(2)28/h6-10,17-21,29-30,32H,11-13H2,1-5H3/t17-,18+,19-,20+,21+,24-,25-,26-/m0/s1
• InChI Key: HRWJAISWJCLGOV-YHVMSLOISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₀
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.21519728 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9480	94.80%
Caco-2	-	0.7111	71.11%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7626	76.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8825	88.25%
OATP1B3 inhibitior	+	0.9271	92.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7907	79.07%
BSEP inhibitior	-	0.6156	61.56%
P-glycoprotein inhibitior	+	0.6648	66.48%
P-glycoprotein substrate	-	0.6669	66.69%
CYP3A4 substrate	+	0.6805	68.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8516	85.16%
CYP3A4 inhibition	-	0.5741	57.41%
CYP2C9 inhibition	-	0.5770	57.70%
CYP2C19 inhibition	-	0.7550	75.50%
CYP2D6 inhibition	-	0.9525	95.25%
CYP1A2 inhibition	-	0.8189	81.89%
CYP2C8 inhibition	+	0.8103	81.03%
CYP inhibitory promiscuity	-	0.8697	86.97%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6623	66.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9154	91.54%
Skin irritation	-	0.6566	65.66%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7144	71.44%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5760	57.60%
skin sensitisation	-	0.9204	92.04%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5862	58.62%
Acute Oral Toxicity (c)	III	0.3706	37.06%
Estrogen receptor binding	+	0.8213	82.13%
Androgen receptor binding	+	0.6743	67.43%
Thyroid receptor binding	+	0.6263	62.63%
Glucocorticoid receptor binding	+	0.5476	54.76%
Aromatase binding	+	0.5890	58.90%
PPAR gamma	+	0.6849	68.49%
Honey bee toxicity	-	0.8537	85.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.93%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	97.13%	90.17%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	95.97%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.06%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.98%	91.11%
CHEMBL5028	O14672	ADAM10	88.62%	97.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	88.55%	91.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.25%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.62%	97.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.96%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.64%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.55%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.31%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.76%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.23%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.11%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.80%	91.19%
CHEMBL2535	P11166	Glucose transporter	80.20%	98.75%

Plants that contains it

• Rzedowskia tolantonguensis

Cross-Links

• PubChem: 163001552
• LOTUS: LTS0228263
• wikiData: Q105032867