[(1Z,3S,3aR,5S,6R,7S,7aR)-1-ethylidene-3,6-bis[[(2S)-2-methylbutanoyl]oxy]-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydroinden-5-yl] (E)-3-methylpent-2-enoate

Details

• Internal ID: 4cf72c62-0b80-46d0-86f1-1b8c2587e44b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1Z,3S,3aR,5S,6R,7S,7aR)-1-ethylidene-3,6-bis[[(2S)-2-methylbutanoyl]oxy]-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydroinden-5-yl] (E)-3-methylpent-2-enoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2C(C(C(=O)C2=CC)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)/C2=C\C)OC(=O)[C@@H](C)CC)C(=C)[C@@H]1OC(=O)/C=C(\C)/CC)[C@]3(CO3)C
• InChI: InChI=1S/C31H44O8/c1-10-16(5)14-21(32)37-26-19(8)22-23(20(13-4)25(33)27(22)38-29(34)17(6)11-2)24(31(9)15-36-31)28(26)39-30(35)18(7)12-3/h13-14,17-18,22-24,26-28H,8,10-12,15H2,1-7,9H3/b16-14+,20-13-/t17-,18-,22-,23+,24-,26-,27-,28+,31+/m0/s1
• InChI Key: WAQPPOMZPIGXAQ-SZJORUNGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₈
• Molecular Weight: 544.70 g/mol
• Exact Mass: 544.30361836 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.91
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 10

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	-	0.7158	71.58%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5740	57.40%
OATP2B1 inhibitior	-	0.7168	71.68%
OATP1B1 inhibitior	+	0.8210	82.10%
OATP1B3 inhibitior	+	0.9170	91.70%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9506	95.06%
P-glycoprotein inhibitior	+	0.8888	88.88%
P-glycoprotein substrate	+	0.5608	56.08%
CYP3A4 substrate	+	0.6690	66.90%
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	-	0.5716	57.16%
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	-	0.8759	87.59%
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	-	0.5000	50.00%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5625	56.25%
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	+	0.6794	67.94%
Acute Oral Toxicity (c)	III	0.5018	50.18%
Estrogen receptor binding	+	0.6913	69.13%
Androgen receptor binding	+	0.7148	71.48%
Thyroid receptor binding	+	0.5399	53.99%
Glucocorticoid receptor binding	+	0.7672	76.72%
Aromatase binding	+	0.6488	64.88%
PPAR gamma	+	0.6205	62.05%
Honey bee toxicity	-	0.6704	67.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
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	97.96%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.36%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.62%	89.34%
CHEMBL2581	P07339	Cathepsin D	93.91%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.79%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.13%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	90.81%	89.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.78%	95.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.17%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.47%	96.61%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.20%	97.28%
CHEMBL1937	Q92769	Histone deacetylase 2	85.96%	94.75%
CHEMBL221	P23219	Cyclooxygenase-1	85.92%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.26%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.54%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.90%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.01%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.49%	95.71%
CHEMBL5255	O00206	Toll-like receptor 4	81.23%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.91%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.54%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.33%	92.62%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.09%	97.47%

Plants that contains it

• Pittocaulon filare

Cross-Links

• PubChem: 90683361
• LOTUS: LTS0246476
• wikiData: Q105300419