beta-Cyclocostunolide

Details

• Internal ID: 143f59ad-948a-46eb-b347-a433847b8185
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aS,5aR,9aS,9bS)-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC12CCCC(=C)C1C3C(CC2)C(=C)C(=O)O3
• SMILES (Isomeric): C[C@]12CCCC(=C)[C@@H]1[C@@H]3[C@@H](CC2)C(=C)C(=O)O3
• InChI: InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15+/m0/s1
• InChI Key: XUYAKPXYKQEFPD-SFDCQRBFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 2221-82-1
• CID 442192
• (3aS,5aR,9aS,9bS)-5a-methyl-3,9-dimethylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
• (3aS,5aR,9aS,9bS)-5a-methyl-3,9-dimethylene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g]benzofuran-2-one
• C09384
• CHEMBL4759939
• SCHEMBL15941718
• CHEBI:10364
• DTXSID60331766
• Naphtho[1,2-b]furan-2(3H)-one, decahydro-5a-methyl-3,9-dimethylene-, (3aS,5aR,9aS,9bS)-
• Q27108625

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7703	77.03%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4018	40.18%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.8468	84.68%
OATP1B3 inhibitior	+	0.8959	89.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.9845	98.45%
P-glycoprotein inhibitior	-	0.8818	88.18%
P-glycoprotein substrate	-	0.9318	93.18%
CYP3A4 substrate	+	0.5677	56.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.5586	55.86%
CYP2C9 inhibition	-	0.9198	91.98%
CYP2C19 inhibition	+	0.8604	86.04%
CYP2D6 inhibition	-	0.9374	93.74%
CYP1A2 inhibition	+	0.9090	90.90%
CYP2C8 inhibition	-	0.7131	71.31%
CYP inhibitory promiscuity	-	0.6896	68.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4480	44.80%
Eye corrosion	-	0.9683	96.83%
Eye irritation	-	0.4917	49.17%
Skin irritation	+	0.4896	48.96%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.7764	77.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5138	51.38%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	+	0.5470	54.70%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6049	60.49%
Acute Oral Toxicity (c)	III	0.6872	68.72%
Estrogen receptor binding	-	0.5447	54.47%
Androgen receptor binding	+	0.6589	65.89%
Thyroid receptor binding	-	0.6875	68.75%
Glucocorticoid receptor binding	-	0.4727	47.27%
Aromatase binding	-	0.7196	71.96%
PPAR gamma	-	0.7379	73.79%
Honey bee toxicity	-	0.8164	81.64%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.21%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.80%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.64%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.14%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.60%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.97%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.56%	96.00%
CHEMBL4530	P00488	Coagulation factor XIII	83.51%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.44%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.40%	93.04%
CHEMBL1902	P62942	FK506-binding protein 1A	80.09%	97.05%

Plants that contains it

• Aucklandia costus
• Bidens subalternans
• Commiphora myrrha
• Frullania tamarisci
• Frullania usamiensis
• Loxothysanus sinuatus
• Magnolia sinica
• Moquiniastrum paniculatum
• Oxylobus arbutifolius
• Oxylobus oaxacanus
• Zea mays

Cross-Links

• PubChem: 442192
• NPASS: NPC203912
• LOTUS: LTS0118747
• wikiData: Q27108625