[(1R,2R,4R,5S,6R,7R,8R,9R,12S,13S)-4,12-diacetyloxy-5,13-dihydroxy-9,13-dimethyl-3-methylidene-6-propan-2-yl-15-oxatricyclo[6.6.1.02,7]pentadecan-9-yl] butanoate

Details

• Internal ID: bfb63394-5407-474d-9f35-351651f2969b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Eunicellane and asbestinane diterpenoids
• IUPAC Name: [(1R,2R,4R,5S,6R,7R,8R,9R,12S,13S)-4,12-diacetyloxy-5,13-dihydroxy-9,13-dimethyl-3-methylidene-6-propan-2-yl-15-oxatricyclo[6.6.1.02,7]pentadecan-9-yl] butanoate
• SMILES (Canonical): CCCC(=O)OC1(CCC(C(CC2C3C(C1O2)C(C(C(C3=C)OC(=O)C)O)C(C)C)(C)O)OC(=O)C)C
• SMILES (Isomeric): CCCC(=O)O[C@@]1(CC[C@@H]([C@@](C[C@@H]2[C@@H]3[C@H]([C@H]1O2)[C@H]([C@@H]([C@@H](C3=C)OC(=O)C)O)C(C)C)(C)O)OC(=O)C)C
• InChI: InChI=1S/C28H44O9/c1-9-10-20(31)37-28(8)12-11-19(34-16(5)29)27(7,33)13-18-22-15(4)25(35-17(6)30)24(32)21(14(2)3)23(22)26(28)36-18/h14,18-19,21-26,32-33H,4,9-13H2,1-3,5-8H3/t18-,19+,21-,22-,23-,24+,25-,26-,27+,28-/m1/s1
• InChI Key: DTUDIIINYUDZEQ-GUBLYABASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O₉
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.29853298 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.09
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.7233	72.33%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7294	72.94%
OATP2B1 inhibitior	-	0.8638	86.38%
OATP1B1 inhibitior	+	0.8349	83.49%
OATP1B3 inhibitior	+	0.8382	83.82%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6723	67.23%
P-glycoprotein inhibitior	+	0.6677	66.77%
P-glycoprotein substrate	+	0.6592	65.92%
CYP3A4 substrate	+	0.6971	69.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8554	85.54%
CYP3A4 inhibition	+	0.8165	81.65%
CYP2C9 inhibition	-	0.5431	54.31%
CYP2C19 inhibition	-	0.5871	58.71%
CYP2D6 inhibition	-	0.9262	92.62%
CYP1A2 inhibition	-	0.6775	67.75%
CYP2C8 inhibition	+	0.5309	53.09%
CYP inhibitory promiscuity	-	0.8007	80.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5941	59.41%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9044	90.44%
Skin irritation	+	0.5965	59.65%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	-	0.6824	68.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5789	57.89%
skin sensitisation	-	0.8177	81.77%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5952	59.52%
Acute Oral Toxicity (c)	I	0.3424	34.24%
Estrogen receptor binding	+	0.7537	75.37%
Androgen receptor binding	+	0.5491	54.91%
Thyroid receptor binding	-	0.5097	50.97%
Glucocorticoid receptor binding	+	0.6482	64.82%
Aromatase binding	+	0.6959	69.59%
PPAR gamma	+	0.6357	63.57%
Honey bee toxicity	-	0.7977	79.77%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	0.9966	99.66%

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	98.87%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.82%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.21%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	94.96%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.38%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.79%	89.05%
CHEMBL255	P29275	Adenosine A2b receptor	90.64%	98.59%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.98%	92.62%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.95%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	89.83%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.93%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.27%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.83%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.35%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	86.34%	92.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.69%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.36%	99.17%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.12%	97.47%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.29%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.82%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.80%	94.33%
CHEMBL2996	Q05655	Protein kinase C delta	83.48%	97.79%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.25%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.99%	95.89%
CHEMBL1871	P10275	Androgen Receptor	82.98%	96.43%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.96%	91.24%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	81.28%	99.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.02%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.69%	96.21%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.19%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.16%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 73346220
• LOTUS: LTS0226990
• wikiData: Q104989037