[(1S,2S,6S,8R,9R,10S,12R,14S)-10-hydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] (3S)-3-methylpentanoate

Details

• Internal ID: 83a59dbc-22a2-430a-9979-b9c0bdec3699
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(1S,2S,6S,8R,9R,10S,12R,14S)-10-hydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[7.5.0.02,6.012,14]tetradecan-8-yl] (3S)-3-methylpentanoate
• SMILES (Canonical): CCC(C)CC(=O)OC1CC2C(C3C1(C(CC4C3(O4)C)O)C)OC(=O)C2=C
• SMILES (Isomeric): CC[C@H](C)CC(=O)O[C@@H]1C[C@@H]2[C@@H]([C@@H]3[C@@]1([C@H](C[C@@H]4[C@]3(O4)C)O)C)OC(=O)C2=C
• InChI: InChI=1S/C21H30O6/c1-6-10(2)7-16(23)25-14-8-12-11(3)19(24)26-17(12)18-20(14,4)13(22)9-15-21(18,5)27-15/h10,12-15,17-18,22H,3,6-9H2,1-2,4-5H3/t10-,12-,13-,14+,15+,17-,18+,20+,21+/m0/s1
• InChI Key: XNGMVHWVFLLJHO-HLYRCDGESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.20423867 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4884	48.84%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8551	85.51%
OATP1B3 inhibitior	+	0.8581	85.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6530	65.30%
P-glycoprotein inhibitior	-	0.5473	54.73%
P-glycoprotein substrate	-	0.5502	55.02%
CYP3A4 substrate	+	0.6779	67.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8846	88.46%
CYP3A4 inhibition	+	0.7917	79.17%
CYP2C9 inhibition	-	0.7724	77.24%
CYP2C19 inhibition	-	0.7943	79.43%
CYP2D6 inhibition	-	0.9419	94.19%
CYP1A2 inhibition	-	0.7991	79.91%
CYP2C8 inhibition	-	0.6276	62.76%
CYP inhibitory promiscuity	-	0.7610	76.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5242	52.42%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.5262	52.62%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5398	53.98%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6858	68.58%
skin sensitisation	-	0.7456	74.56%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6044	60.44%
Acute Oral Toxicity (c)	III	0.3321	33.21%
Estrogen receptor binding	+	0.8188	81.88%
Androgen receptor binding	+	0.6469	64.69%
Thyroid receptor binding	+	0.5672	56.72%
Glucocorticoid receptor binding	+	0.7943	79.43%
Aromatase binding	+	0.6310	63.10%
PPAR gamma	+	0.6910	69.10%
Honey bee toxicity	-	0.7387	73.87%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9958	99.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.95%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.44%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	92.93%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.30%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.47%	96.61%
CHEMBL299	P17252	Protein kinase C alpha	88.31%	98.03%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.84%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.89%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.59%	92.62%
CHEMBL221	P23219	Cyclooxygenase-1	85.26%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.79%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.98%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.65%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.46%	96.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.44%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.21%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.01%	89.00%

Plants that contains it

• Pluchea dioscoridis

Cross-Links

• PubChem: 162984391
• LOTUS: LTS0048693
• wikiData: Q105331635