[(3aR,4R,6aR,8S,9aR,9bR)-8-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[2-(4-hydroxyphenyl)acetyl]oxyoxan-2-yl]oxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R,3S)-2-hydroxy-3-methylpentanoate

Details

• Internal ID: 9f4163ff-d98f-450d-a13e-993a01168636
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6aR,8S,9aR,9bR)-8-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[2-(4-hydroxyphenyl)acetyl]oxyoxan-2-yl]oxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R,3S)-2-hydroxy-3-methylpentanoate
• SMILES (Canonical): CCC(C)C(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)OC4C(C(C(C(O4)CO)OC(=O)CC5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): CC[C@H](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)CO)OC(=O)CC5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C35H44O13/c1-6-15(2)28(39)34(43)44-23-11-16(3)21-13-22(17(4)26(21)32-27(23)18(5)33(42)48-32)45-35-30(41)29(40)31(24(14-36)46-35)47-25(38)12-19-7-9-20(37)10-8-19/h7-10,15,21-24,26-32,35-37,39-41H,3-6,11-14H2,1-2H3/t15-,21-,22-,23+,24+,26-,27+,28+,29+,30+,31+,32+,35+/m0/s1
• InChI Key: UADGOOWLIBGZGY-MFVKXWHRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₃
• Molecular Weight: 672.70 g/mol
• Exact Mass: 672.27819145 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.24
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9244	92.44%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7489	74.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7885	78.85%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7090	70.90%
P-glycoprotein inhibitior	+	0.6610	66.10%
P-glycoprotein substrate	+	0.6859	68.59%
CYP3A4 substrate	+	0.7118	71.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8827	88.27%
CYP3A4 inhibition	+	0.6223	62.23%
CYP2C9 inhibition	-	0.6826	68.26%
CYP2C19 inhibition	-	0.5456	54.56%
CYP2D6 inhibition	-	0.9036	90.36%
CYP1A2 inhibition	-	0.7638	76.38%
CYP2C8 inhibition	+	0.7049	70.49%
CYP inhibitory promiscuity	-	0.6066	60.66%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5843	58.43%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9108	91.08%
Skin irritation	-	0.7442	74.42%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5966	59.66%
skin sensitisation	-	0.7996	79.96%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7235	72.35%
Acute Oral Toxicity (c)	III	0.5501	55.01%
Estrogen receptor binding	+	0.8335	83.35%
Androgen receptor binding	+	0.6968	69.68%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.6878	68.78%
PPAR gamma	+	0.6717	67.17%
Honey bee toxicity	-	0.6408	64.08%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9955	99.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.30%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.16%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.81%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	93.65%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.63%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.62%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.93%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.10%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.19%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.62%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.43%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.12%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.45%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.42%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.99%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.81%	95.83%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.38%	96.37%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.24%	90.08%
CHEMBL220	P22303	Acetylcholinesterase	81.22%	94.45%
CHEMBL2514	O95665	Neurotensin receptor 2	80.95%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.90%	82.50%

Plants that contains it

• Alangium platanifolium
• Crataegus pinnatifida
• Hydrangea macrophylla
• Ixeris stolonifera

Cross-Links

• PubChem: 162925679
• LOTUS: LTS0197997
• wikiData: Q105186407