(3aR,4S,6E,10Z,11aR)-2,3,3a,4,5,8,9,11a-Octahydro-4-hydroxy-10-[[6-O-[(4-hydroxyphenyl)acetyl]-beta-D-glucopyranosyl]oxymethyl]-3-methylene-2-oxocyclodeca[b]furan-6-carbaldehyde

Details

• Internal ID: 1f6dd5da-9a56-481c-8b0f-1dff7b43e48f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3aR,4S,6E,10Z,11aR)-6-formyl-4-hydroxy-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-10-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): C=C1C2C(CC(=CCCC(=CC2OC1=O)COC3C(C(C(C(O3)COC(=O)CC4=CC=C(C=C4)O)O)O)O)C=O)O
• SMILES (Isomeric): C=C1[C@@H]2[C@H](C/C(=C\CC/C(=C/[C@H]2OC1=O)/CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)CC4=CC=C(C=C4)O)O)O)O)/C=O)O
• InChI: InChI=1S/C29H34O12/c1-15-24-20(32)9-17(12-30)3-2-4-18(10-21(24)40-28(15)37)13-39-29-27(36)26(35)25(34)22(41-29)14-38-23(33)11-16-5-7-19(31)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-32,34-36H,1-2,4,9,11,13-14H2/b17-3+,18-10-/t20-,21+,22+,24+,25+,26-,27+,29+/m0/s1
• InChI Key: NGDUYKZDYOOZLX-IPTIBXCDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₂
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.20502652 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6864	68.64%
Caco-2	-	0.8839	88.39%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7976	79.76%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8121	81.21%
OATP1B3 inhibitior	+	0.9517	95.17%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6215	62.15%
P-glycoprotein inhibitior	+	0.6128	61.28%
P-glycoprotein substrate	-	0.5392	53.92%
CYP3A4 substrate	+	0.6809	68.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8770	87.70%
CYP3A4 inhibition	-	0.7510	75.10%
CYP2C9 inhibition	-	0.8739	87.39%
CYP2C19 inhibition	-	0.6805	68.05%
CYP2D6 inhibition	-	0.8341	83.41%
CYP1A2 inhibition	-	0.7469	74.69%
CYP2C8 inhibition	+	0.7441	74.41%
CYP inhibitory promiscuity	-	0.8812	88.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5975	59.75%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9176	91.76%
Skin irritation	-	0.7798	77.98%
Skin corrosion	-	0.9460	94.60%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8057	80.57%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6291	62.91%
Acute Oral Toxicity (c)	III	0.4674	46.74%
Estrogen receptor binding	+	0.8223	82.23%
Androgen receptor binding	+	0.5960	59.60%
Thyroid receptor binding	-	0.5452	54.52%
Glucocorticoid receptor binding	+	0.5395	53.95%
Aromatase binding	+	0.5810	58.10%
PPAR gamma	+	0.7037	70.37%
Honey bee toxicity	-	0.7099	70.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9805	98.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.42%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.32%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.34%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.05%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.67%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	92.19%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.02%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.16%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.51%	97.33%
CHEMBL2581	P07339	Cathepsin D	88.91%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.02%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.82%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.62%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.87%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.58%	86.33%
CHEMBL2954	P25774	Cathepsin S	84.70%	95.60%
CHEMBL3891	P07384	Calpain 1	84.41%	93.04%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.32%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.04%	95.89%
CHEMBL5957	P21589	5'-nucleotidase	81.64%	97.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.38%	97.36%

Plants that contains it

• Origanum vulgare
• Sonchus asper
• Urospermum picroides

Cross-Links

• PubChem: 101701130
• NPASS: NPC145579
• LOTUS: LTS0261826
• wikiData: Q105178847