[(E)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-[[(2S,3S,4R,5S)-3,4,5-triacetyloxyoxan-2-yl]oxymethyl]pent-2-enyl] acetate

Details

• Internal ID: 7f088f2f-8d5c-4d48-a5a6-6c9cf4182b37
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: [(E)-5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-[[(2S,3S,4R,5S)-3,4,5-triacetyloxyoxan-2-yl]oxymethyl]pent-2-enyl] acetate
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CCOC(=O)C)COC3C(C(C(CO3)OC(=O)C)OC(=O)C)OC(=O)C)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C\COC(=O)C)/CO[C@@H]3[C@H]([C@@H]([C@H](CO3)OC(=O)C)OC(=O)C)OC(=O)C)CCC=C2C)C
• InChI: InChI=1S/C33H50O10/c1-20-10-9-11-28-32(20,7)15-12-21(2)33(28,8)16-13-26(14-17-38-22(3)34)18-39-31-30(43-25(6)37)29(42-24(5)36)27(19-40-31)41-23(4)35/h10,14,21,27-31H,9,11-13,15-19H2,1-8H3/b26-14+/t21-,27+,28+,29-,30+,31+,32+,33+/m1/s1
• InChI Key: UAAAHAUBORUCMG-YVTNKQPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₁₀
• Molecular Weight: 606.70 g/mol
• Exact Mass: 606.34039779 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.22
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9626	96.26%
Caco-2	-	0.7939	79.39%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7888	78.88%
OATP2B1 inhibitior	-	0.7143	71.43%
OATP1B1 inhibitior	+	0.8526	85.26%
OATP1B3 inhibitior	+	0.9320	93.20%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9124	91.24%
P-glycoprotein inhibitior	+	0.8502	85.02%
P-glycoprotein substrate	-	0.6062	60.62%
CYP3A4 substrate	+	0.6962	69.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8926	89.26%
CYP2C9 inhibition	-	0.9460	94.60%
CYP2C19 inhibition	-	0.8501	85.01%
CYP2D6 inhibition	-	0.9565	95.65%
CYP1A2 inhibition	-	0.7216	72.16%
CYP2C8 inhibition	+	0.6448	64.48%
CYP inhibitory promiscuity	-	0.8449	84.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6141	61.41%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9183	91.83%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.5166	51.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.6835	68.35%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6068	60.68%
skin sensitisation	-	0.8733	87.33%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5884	58.84%
Acute Oral Toxicity (c)	III	0.4723	47.23%
Estrogen receptor binding	+	0.7484	74.84%
Androgen receptor binding	+	0.6124	61.24%
Thyroid receptor binding	-	0.5349	53.49%
Glucocorticoid receptor binding	+	0.7744	77.44%
Aromatase binding	+	0.7063	70.63%
PPAR gamma	+	0.6695	66.95%
Honey bee toxicity	-	0.7429	74.29%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.9839	98.39%

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	97.95%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.38%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.23%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.57%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.17%	97.09%
CHEMBL5028	O14672	ADAM10	86.25%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	85.21%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.07%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.91%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.76%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.09%	86.33%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	83.26%	95.52%
CHEMBL2581	P07339	Cathepsin D	82.08%	98.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.07%	97.28%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.00%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	81.44%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.75%	93.00%

Plants that contains it

• Baccharis boliviensis

Cross-Links

• PubChem: 162850204
• LOTUS: LTS0157380
• wikiData: Q103788473