[(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[2-(4-hydroxyphenyl)acetyl]oxymethyl]oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate

Details

• Internal ID: 5ba21352-5b84-4b26-ae97-480be80a1dab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[2-(4-hydroxyphenyl)acetyl]oxymethyl]oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate
• SMILES (Canonical): CC(C)C(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)OC4C(C(C(C(O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): CC(C)[C@H](C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C34H42O13/c1-14(2)27(37)33(42)44-22-10-15(3)20-12-21(16(4)25(20)31-26(22)17(5)32(41)47-31)45-34-30(40)29(39)28(38)23(46-34)13-43-24(36)11-18-6-8-19(35)9-7-18/h6-9,14,20-23,25-31,34-35,37-40H,3-5,10-13H2,1-2H3/t20-,21-,22+,23+,25-,26+,27+,28+,29-,30+,31+,34+/m0/s1
• InChI Key: SGEAESJBAYKDCK-RRSVAXDHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₃
• Molecular Weight: 658.70 g/mol
• Exact Mass: 658.26254139 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.85
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8047	80.47%
Caco-2	-	0.8723	87.23%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7843	78.43%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.8097	80.97%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5949	59.49%
P-glycoprotein inhibitior	+	0.6543	65.43%
P-glycoprotein substrate	+	0.6439	64.39%
CYP3A4 substrate	+	0.7094	70.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8840	88.40%
CYP3A4 inhibition	-	0.5675	56.75%
CYP2C9 inhibition	-	0.6663	66.63%
CYP2C19 inhibition	-	0.5746	57.46%
CYP2D6 inhibition	-	0.8439	84.39%
CYP1A2 inhibition	-	0.7919	79.19%
CYP2C8 inhibition	+	0.6653	66.53%
CYP inhibitory promiscuity	-	0.5497	54.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9102	91.02%
Skin irritation	-	0.7613	76.13%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.6143	61.43%
skin sensitisation	-	0.7672	76.72%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.5447	54.47%
Estrogen receptor binding	+	0.8323	83.23%
Androgen receptor binding	+	0.6581	65.81%
Thyroid receptor binding	+	0.5203	52.03%
Glucocorticoid receptor binding	+	0.6645	66.45%
Aromatase binding	+	0.6656	66.56%
PPAR gamma	+	0.6872	68.72%
Honey bee toxicity	-	0.6504	65.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9940	99.40%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.36%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.58%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.65%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.83%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.39%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.65%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.86%	95.50%
CHEMBL220	P22303	Acetylcholinesterase	89.49%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	89.19%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.85%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.72%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.28%	90.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.40%	99.17%
CHEMBL2535	P11166	Glucose transporter	86.04%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	85.59%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.02%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.82%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.97%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.31%	95.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.32%	90.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.90%	85.31%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.02%	97.33%

Plants that contains it

• Ixeris japonica
• Ixeris stolonifera

Cross-Links

• PubChem: 162893312
• LOTUS: LTS0004312
• wikiData: Q105252247