[(1S,2S,4R,7R,10R,11R,12R)-4-hydroxy-1,5-dimethyl-9-oxo-8-oxatetracyclo[8.3.1.02,6.07,11]tetradec-5-en-12-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 1c13a38e-7dd4-4ccf-a019-2adc1c040e47
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(1S,2S,4R,7R,10R,11R,12R)-4-hydroxy-1,5-dimethyl-9-oxo-8-oxatetracyclo[8.3.1.02,6.07,11]tetradec-5-en-12-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2(CC3C1C(C4=C(C(CC42)O)C)OC3=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1C[C@@]2(C[C@@H]3[C@H]1[C@H](C4=C([C@@H](C[C@H]42)O)C)OC3=O)C
• InChI: InChI=1S/C20H28O5/c1-5-9(2)18(22)24-14-8-20(4)7-11-16(14)17(25-19(11)23)15-10(3)13(21)6-12(15)20/h9,11-14,16-17,21H,5-8H2,1-4H3/t9-,11-,12-,13-,14-,16-,17+,20+/m1/s1
• InChI Key: HSJMRBFKPJRDID-UOTGQVGFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.6718	67.18%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5864	58.64%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8646	86.46%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7436	74.36%
P-glycoprotein inhibitior	-	0.5848	58.48%
P-glycoprotein substrate	-	0.6628	66.28%
CYP3A4 substrate	+	0.6262	62.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	+	0.5693	56.93%
CYP2C9 inhibition	-	0.7931	79.31%
CYP2C19 inhibition	-	0.8344	83.44%
CYP2D6 inhibition	-	0.9611	96.11%
CYP1A2 inhibition	-	0.7461	74.61%
CYP2C8 inhibition	-	0.6773	67.73%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5451	54.51%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9108	91.08%
Skin irritation	+	0.5668	56.68%
Skin corrosion	-	0.9256	92.56%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4114	41.14%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5360	53.60%
skin sensitisation	-	0.7692	76.92%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8182	81.82%
Acute Oral Toxicity (c)	III	0.4258	42.58%
Estrogen receptor binding	+	0.7262	72.62%
Androgen receptor binding	+	0.6447	64.47%
Thyroid receptor binding	+	0.5552	55.52%
Glucocorticoid receptor binding	+	0.6309	63.09%
Aromatase binding	-	0.5615	56.15%
PPAR gamma	-	0.6108	61.08%
Honey bee toxicity	-	0.7890	78.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5596	55.96%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.94%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.62%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	96.20%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.06%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.50%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.37%	96.47%
CHEMBL2581	P07339	Cathepsin D	90.55%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.38%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.82%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.42%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	84.99%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.33%	95.71%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.57%	96.61%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.34%	97.21%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.88%	96.38%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.30%	90.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.05%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.02%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.54%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.36%	92.50%

Plants that contains it

• Artemisia pontica

Cross-Links

• PubChem: 162888190
• LOTUS: LTS0220183
• wikiData: Q105033089