[(3aR,4R,6R,6aS,7R,9aR,9bR)-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: dc3fcfbf-6fdf-493e-9493-161f2e83ccf4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6R,6aS,7R,9aR,9bR)-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC1=CC(C2C1C3C(C(CC24CO4)OC(=O)C(=CCO)CO)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=C[C@H]([C@@H]2[C@H]1[C@@H]3[C@@H]([C@@H](C[C@]24CO4)OC(=O)/C(=C/CO)/CO)C(=C)C(=O)O3)O
• InChI: InChI=1S/C20H24O8/c1-9-5-12(23)16-14(9)17-15(10(2)18(24)28-17)13(6-20(16)8-26-20)27-19(25)11(7-22)3-4-21/h3,5,12-17,21-23H,2,4,6-8H2,1H3/b11-3+/t12-,13-,14+,15-,16-,17-,20+/m1/s1
• InChI Key: NAJVQNXNVGBDAW-VWXFNEHMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₈
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.14711772 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8978	89.78%
Caco-2	-	0.7495	74.95%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6966	69.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6705	67.05%
P-glycoprotein inhibitior	-	0.6559	65.59%
P-glycoprotein substrate	-	0.5743	57.43%
CYP3A4 substrate	+	0.6659	66.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8716	87.16%
CYP3A4 inhibition	-	0.8807	88.07%
CYP2C9 inhibition	-	0.8274	82.74%
CYP2C19 inhibition	-	0.7935	79.35%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8337	83.37%
CYP2C8 inhibition	-	0.6080	60.80%
CYP inhibitory promiscuity	-	0.8306	83.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4903	49.03%
Eye corrosion	-	0.9704	97.04%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.7006	70.06%
Skin corrosion	-	0.8965	89.65%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6418	64.18%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.7362	73.62%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.8935	89.35%
Acute Oral Toxicity (c)	III	0.4074	40.74%
Estrogen receptor binding	+	0.8748	87.48%
Androgen receptor binding	+	0.6481	64.81%
Thyroid receptor binding	+	0.5675	56.75%
Glucocorticoid receptor binding	+	0.7472	74.72%
Aromatase binding	+	0.6907	69.07%
PPAR gamma	+	0.6370	63.70%
Honey bee toxicity	-	0.6548	65.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8958	89.58%

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	97.50%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.83%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	91.92%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.96%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.98%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	88.87%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.72%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.84%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.60%	96.09%
CHEMBL2581	P07339	Cathepsin D	84.98%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.93%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	84.91%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.82%	89.34%
CHEMBL2996	Q05655	Protein kinase C delta	83.71%	97.79%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.27%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.26%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.23%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.04%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.04%	97.28%

Plants that contains it

• Eupatorium altissimum

Cross-Links

• PubChem: 163014924
• LOTUS: LTS0263641
• wikiData: Q105176355