CID 21581065

Details

• Internal ID: f4666431-839e-46c4-a8cc-a58b5691facd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(3S,3aS,5R,5aR,6R,7R,9R,9aR)-5-[(E,2R)-2-hydroxy-3-methylpent-3-enoyl]oxy-7-(2-hydroxypropan-2-yl)-6-(3-methoxy-3-oxopropyl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-9-yl] (E,2R)-2-hydroxy-3-methylpent-3-enoate
• SMILES (Canonical): CC=C(C)C(C(=O)OC1CC(C(C2C1(C3=CCC(C3(CC2OC(=O)C(C(=CC)C)O)C)C4CC(OC4)C=C(C)C)C)(C)CCC(=O)OC)C(C)(C)O)O
• SMILES (Isomeric): C/C=C(\C)/[C@H](C(=O)O[C@@H]1C[C@H]([C@]([C@@H]2[C@@]1(C3=CC[C@H]([C@@]3(C[C@H]2OC(=O)[C@@H](/C(=C/C)/C)O)C)[C@@H]4C[C@H](OC4)C=C(C)C)C)(C)CCC(=O)OC)C(C)(C)O)O
• InChI: InChI=1S/C43H66O10/c1-13-25(5)35(45)38(47)52-30-22-42(10)29(27-20-28(51-23-27)19-24(3)4)15-16-31(42)43(11)33(53-39(48)36(46)26(6)14-2)21-32(40(7,8)49)41(9,37(30)43)18-17-34(44)50-12/h13-14,16,19,27-30,32-33,35-37,45-46,49H,15,17-18,20-23H2,1-12H3/b25-13+,26-14+/t27-,28-,29+,30-,32+,33-,35-,36-,37-,41+,42+,43-/m1/s1
• InChI Key: WPEKKKYUGODPOL-JMRWPWSNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₆₆O₁₀
• Molecular Weight: 743.00 g/mol
• Exact Mass: 742.46559830 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 6.56
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.8396	83.96%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.9000	90.00%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8495	84.95%
OATP1B3 inhibitior	+	0.8935	89.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7114	71.14%
BSEP inhibitior	+	0.9831	98.31%
P-glycoprotein inhibitior	+	0.8012	80.12%
P-glycoprotein substrate	+	0.7229	72.29%
CYP3A4 substrate	+	0.7388	73.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.5056	50.56%
CYP2C9 inhibition	-	0.6622	66.22%
CYP2C19 inhibition	-	0.8579	85.79%
CYP2D6 inhibition	-	0.9285	92.85%
CYP1A2 inhibition	-	0.8047	80.47%
CYP2C8 inhibition	+	0.7451	74.51%
CYP inhibitory promiscuity	-	0.7010	70.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5452	54.52%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.5862	58.62%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4136	41.36%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6335	63.35%
Acute Oral Toxicity (c)	III	0.5032	50.32%
Estrogen receptor binding	+	0.7641	76.41%
Androgen receptor binding	+	0.7371	73.71%
Thyroid receptor binding	+	0.5781	57.81%
Glucocorticoid receptor binding	+	0.7859	78.59%
Aromatase binding	+	0.6560	65.60%
PPAR gamma	+	0.7777	77.77%
Honey bee toxicity	-	0.5522	55.22%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.99%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.79%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.91%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.68%	97.25%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	95.20%	97.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.14%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.07%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.84%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.00%	91.19%
CHEMBL5028	O14672	ADAM10	88.17%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.66%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.82%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	86.38%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.90%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.46%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.23%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.41%	96.77%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.98%	96.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.47%	92.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.07%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.86%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.78%	93.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.64%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.28%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.12%	96.00%

Plants that contains it

• Aglaia argentea

Cross-Links

• PubChem: 21581065
• LOTUS: LTS0101693
• wikiData: Q105309830