[(1S,3S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-acetyloxyethyl]-3,6-bis[[(2S)-2-methylbutanoyl]oxy]-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate

Details

• Internal ID: 525f0d0f-5ac8-410a-814a-3ad675bad56d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,3S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-acetyloxyethyl]-3,6-bis[[(2S)-2-methylbutanoyl]oxy]-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2C(C(C(=O)C2C(C)OC(=O)C)OC(=O)C(C)CC)C(=C)C1OC(=O)C=C(C)CC)C3(CO3)C
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@@H]1[C@H]([C@H]2[C@@H]([C@@H](C(=O)[C@@H]2[C@@H](C)OC(=O)C)OC(=O)[C@@H](C)CC)C(=C)[C@@H]1OC(=O)/C=C(\C)/CC)[C@]3(CO3)C
• InChI: InChI=1S/C33H48O10/c1-11-16(4)14-22(35)41-28-19(7)23-25(26(33(10)15-39-33)30(28)43-32(38)18(6)13-3)24(20(8)40-21(9)34)27(36)29(23)42-31(37)17(5)12-2/h14,17-18,20,23-26,28-30H,7,11-13,15H2,1-6,8-10H3/b16-14+/t17-,18-,20+,23-,24+,25-,26-,28-,29-,30+,33+/m0/s1
• InChI Key: UVGXCJSBXINHLC-CWNOTTLPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₈O₁₀
• Molecular Weight: 604.70 g/mol
• Exact Mass: 604.32474772 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.53
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9936	99.36%
Caco-2	-	0.7763	77.63%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5740	57.40%
OATP2B1 inhibitior	-	0.7126	71.26%
OATP1B1 inhibitior	+	0.8201	82.01%
OATP1B3 inhibitior	+	0.9170	91.70%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9513	95.13%
P-glycoprotein inhibitior	+	0.8548	85.48%
P-glycoprotein substrate	+	0.5758	57.58%
CYP3A4 substrate	+	0.6739	67.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8961	89.61%
CYP3A4 inhibition	-	0.6794	67.94%
CYP2C9 inhibition	-	0.7373	73.73%
CYP2C19 inhibition	-	0.6621	66.21%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.6225	62.25%
CYP2C8 inhibition	+	0.5263	52.63%
CYP inhibitory promiscuity	-	0.5414	54.14%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6002	60.02%
Eye corrosion	-	0.9724	97.24%
Eye irritation	-	0.8754	87.54%
Skin irritation	-	0.6267	62.67%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5838	58.38%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5584	55.84%
skin sensitisation	-	0.6218	62.18%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5726	57.26%
Acute Oral Toxicity (c)	III	0.5018	50.18%
Estrogen receptor binding	+	0.7206	72.06%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	+	0.5605	56.05%
Glucocorticoid receptor binding	+	0.7465	74.65%
Aromatase binding	+	0.6746	67.46%
PPAR gamma	+	0.6493	64.93%
Honey bee toxicity	-	0.6643	66.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9948	99.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.61%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.20%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	94.73%	89.50%
CHEMBL221	P23219	Cyclooxygenase-1	93.16%	90.17%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	91.07%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.02%	96.47%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.30%	89.34%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.18%	97.28%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.90%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	86.63%	94.75%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.00%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	84.81%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.56%	97.25%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.10%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	84.05%	92.50%
CHEMBL230	P35354	Cyclooxygenase-2	83.82%	89.63%
CHEMBL3776	Q14790	Caspase-8	83.65%	97.06%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.60%	97.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.12%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.77%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.81%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.55%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.21%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	80.18%	83.82%

Plants that contains it

• Pittocaulon filare

Cross-Links

• PubChem: 90683360
• LOTUS: LTS0029010
• wikiData: Q105279830