[(1S,2S,6R,7S,9S,12S,13S,15S,16R)-9,12-dihydroxy-15-methyl-5-methylidene-4-oxo-3,11,14-trioxapentacyclo[7.6.1.02,6.012,16.013,15]hexadecan-7-yl] (2S)-2-methylbutanoate

Details

• Internal ID: e9dc826a-1b04-4fbc-814d-ae8cefeff38b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: [(1S,2S,6R,7S,9S,12S,13S,15S,16R)-9,12-dihydroxy-15-methyl-5-methylidene-4-oxo-3,11,14-trioxapentacyclo[7.6.1.02,6.012,16.013,15]hexadecan-7-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2(COC3(C2C(C4C1C(=C)C(=O)O4)C5(C3O5)C)O)O
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@H]1C[C@]2(CO[C@]3([C@@H]2[C@@H]([C@@H]4[C@@H]1C(=C)C(=O)O4)[C@]5([C@@H]3O5)C)O)O
• InChI: InChI=1S/C20H26O8/c1-5-8(2)15(21)26-10-6-19(23)7-25-20(24)14(19)12(18(4)17(20)28-18)13-11(10)9(3)16(22)27-13/h8,10-14,17,23-24H,3,5-7H2,1-2,4H3/t8-,10-,11+,12+,13-,14+,17-,18-,19+,20-/m0/s1
• InChI Key: IIXSMSPNCAECDY-ANQHBOPJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.16276778 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9120	91.20%
Caco-2	-	0.6454	64.54%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5750	57.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8932	89.32%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7449	74.49%
P-glycoprotein inhibitior	-	0.6493	64.93%
P-glycoprotein substrate	-	0.5304	53.04%
CYP3A4 substrate	+	0.6491	64.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8906	89.06%
CYP3A4 inhibition	-	0.5744	57.44%
CYP2C9 inhibition	-	0.7810	78.10%
CYP2C19 inhibition	-	0.8255	82.55%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.8805	88.05%
CYP2C8 inhibition	-	0.6384	63.84%
CYP inhibitory promiscuity	-	0.8243	82.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6052	60.52%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9299	92.99%
Skin irritation	-	0.6590	65.90%
Skin corrosion	-	0.9186	91.86%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4783	47.83%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5908	59.08%
skin sensitisation	-	0.7978	79.78%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5140	51.40%
Acute Oral Toxicity (c)	III	0.5161	51.61%
Estrogen receptor binding	+	0.8810	88.10%
Androgen receptor binding	+	0.6934	69.34%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.7625	76.25%
Aromatase binding	+	0.6600	66.00%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.6832	68.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9213	92.13%

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	98.14%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	96.58%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	96.04%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.17%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.40%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.13%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.98%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.70%	96.47%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.47%	97.28%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.99%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.89%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.42%	99.23%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.57%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.37%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.13%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.54%	92.62%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.33%	89.34%

Plants that contains it

• Eupatorium mohrii

Cross-Links

• PubChem: 162877254
• LOTUS: LTS0267520
• wikiData: Q105113811