[(3aR,4S,5aR,6S,9S,9aS,9bS)-5a-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (Z)-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 1af0c7e9-bf7e-4c1a-95f7-a0db131c8e14
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: [(3aR,4S,5aR,6S,9S,9aS,9bS)-5a-methyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-6-yl] (Z)-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2(C(CCC3(C2C4C1C(=C)C(=O)O4)CO3)OC(=O)C(=CC)CO)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@]2([C@H](CC[C@]3([C@@H]2[C@@H]4[C@@H]1C(=C)C(=O)O4)CO3)OC(=O)/C(=C\C)/CO)C
• InChI: InChI=1S/C25H32O8/c1-6-13(3)21(27)31-16-10-24(5)17(32-23(29)15(7-2)11-26)8-9-25(12-30-25)20(24)19-18(16)14(4)22(28)33-19/h6-7,16-20,26H,4,8-12H2,1-3,5H3/b13-6-,15-7-/t16-,17-,18+,19-,20+,24-,25+/m0/s1
• InChI Key: GDPPSCHOQRGQFP-LOOKUFJOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₈
• Molecular Weight: 460.50 g/mol
• Exact Mass: 460.20971797 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9682	96.82%
Caco-2	-	0.6556	65.56%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7479	74.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8695	86.95%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5479	54.79%
BSEP inhibitior	+	0.6637	66.37%
P-glycoprotein inhibitior	+	0.7619	76.19%
P-glycoprotein substrate	-	0.5590	55.90%
CYP3A4 substrate	+	0.6839	68.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.5410	54.10%
CYP2C9 inhibition	-	0.8208	82.08%
CYP2C19 inhibition	-	0.8548	85.48%
CYP2D6 inhibition	-	0.9391	93.91%
CYP1A2 inhibition	-	0.7611	76.11%
CYP2C8 inhibition	-	0.5765	57.65%
CYP inhibitory promiscuity	-	0.9003	90.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5121	51.21%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9170	91.70%
Skin irritation	-	0.5597	55.97%
Skin corrosion	-	0.9245	92.45%
Ames mutagenesis	-	0.5840	58.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7153	71.53%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5701	57.01%
skin sensitisation	-	0.8348	83.48%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8572	85.72%
Acute Oral Toxicity (c)	III	0.4230	42.30%
Estrogen receptor binding	+	0.7923	79.23%
Androgen receptor binding	+	0.6514	65.14%
Thyroid receptor binding	+	0.6364	63.64%
Glucocorticoid receptor binding	+	0.8349	83.49%
Aromatase binding	+	0.6918	69.18%
PPAR gamma	+	0.7176	71.76%
Honey bee toxicity	-	0.6780	67.80%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	97.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.84%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.60%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.34%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.32%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.20%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.23%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.81%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.54%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.76%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.11%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.02%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.71%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.64%	92.94%
CHEMBL2996	Q05655	Protein kinase C delta	83.24%	97.79%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.57%	97.28%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.26%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.19%	97.14%
CHEMBL2581	P07339	Cathepsin D	80.81%	98.95%

Plants that contains it

• Dimerostemma asperatum
• Dimerostemma lippioides

Cross-Links

• PubChem: 163070121
• LOTUS: LTS0239720
• wikiData: Q105006868