(2S)-1-[[(3R,3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a-methyl-9-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-3-yl]methyl]pyrrolidine-2-carboxylic acid

Details

• Internal ID: 92f6ca42-9c41-4ffe-ae9a-b8ca5dc27177
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (2S)-1-[[(3R,3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a-methyl-9-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-3-yl]methyl]pyrrolidine-2-carboxylic acid
• SMILES (Canonical): CC12CCC3C(C(=O)OC3C1C(=C)CCC2O)CN4CCCC4C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H]3[C@@H](C(=O)O[C@@H]3[C@H]1C(=C)CC[C@H]2O)CN4CCC[C@H]4C(=O)O
• InChI: InChI=1S/C20H29NO5/c1-11-5-6-15(22)20(2)8-7-12-13(19(25)26-17(12)16(11)20)10-21-9-3-4-14(21)18(23)24/h12-17,22H,1,3-10H2,2H3,(H,23,24)/t12-,13-,14-,15+,16+,17-,20-/m0/s1
• InChI Key: KTROAXMUYHQRSZ-GZFXCQGHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.40 g/mol
• Exact Mass: 363.20457303 g/mol
• Topological Polar Surface Area (TPSA): 87.10 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9223	92.23%
Caco-2	-	0.5349	53.49%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5280	52.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8789	87.89%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5694	56.94%
P-glycoprotein inhibitior	-	0.8020	80.20%
P-glycoprotein substrate	-	0.6823	68.23%
CYP3A4 substrate	+	0.6785	67.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7531	75.31%
CYP3A4 inhibition	-	0.7636	76.36%
CYP2C9 inhibition	-	0.9034	90.34%
CYP2C19 inhibition	-	0.8109	81.09%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	-	0.8474	84.74%
CYP2C8 inhibition	-	0.8063	80.63%
CYP inhibitory promiscuity	-	0.9675	96.75%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.5111	51.11%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9469	94.69%
Skin irritation	-	0.7295	72.95%
Skin corrosion	-	0.9109	91.09%
Ames mutagenesis	-	0.6937	69.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6032	60.32%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5971	59.71%
skin sensitisation	-	0.8386	83.86%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8023	80.23%
Acute Oral Toxicity (c)	III	0.6074	60.74%
Estrogen receptor binding	+	0.7548	75.48%
Androgen receptor binding	+	0.7210	72.10%
Thyroid receptor binding	+	0.5150	51.50%
Glucocorticoid receptor binding	+	0.6554	65.54%
Aromatase binding	-	0.5163	51.63%
PPAR gamma	-	0.5359	53.59%
Honey bee toxicity	-	0.8661	86.61%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9663	96.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.54%	97.25%
CHEMBL237	P41145	Kappa opioid receptor	95.86%	98.10%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.46%	96.38%
CHEMBL2581	P07339	Cathepsin D	92.48%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.11%	96.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	88.94%	90.24%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.89%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.77%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.16%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.95%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.90%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.45%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.91%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.52%	98.33%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	81.41%	95.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.87%	89.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.58%	94.78%

Plants that contains it

• Aucklandia costus

Cross-Links

• PubChem: 10406411
• LOTUS: LTS0246208
• wikiData: Q105145945