(3aS,6S,6aS,9bS)-6-hydroxy-6,6a,9-trimethyl-3-methylidene-3a,4,5,7,8,9b-hexahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: ad964179-e84b-475b-8002-c9c5958771dd
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,6S,6aS,9bS)-6-hydroxy-6,6a,9-trimethyl-3-methylidene-3a,4,5,7,8,9b-hexahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2C3C(CCC(C2(CC1)C)(C)O)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=C2[C@@H]3[C@@H](CC[C@]([C@]2(CC1)C)(C)O)C(=C)C(=O)O3
• InChI: InChI=1S/C16H22O3/c1-9-5-7-15(3)12(9)13-11(6-8-16(15,4)18)10(2)14(17)19-13/h11,13,18H,2,5-8H2,1,3-4H3/t11-,13-,15-,16-/m0/s1
• InChI Key: IIIQISVHDIHHNB-MZGVZZPPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.34 g/mol
• Exact Mass: 262.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.75
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.7554	75.54%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6410	64.10%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.9435	94.35%
P-glycoprotein inhibitior	-	0.8825	88.25%
P-glycoprotein substrate	-	0.9312	93.12%
CYP3A4 substrate	+	0.6069	60.69%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8625	86.25%
CYP3A4 inhibition	-	0.6798	67.98%
CYP2C9 inhibition	-	0.7616	76.16%
CYP2C19 inhibition	-	0.6963	69.63%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	+	0.6496	64.96%
CYP2C8 inhibition	-	0.7723	77.23%
CYP inhibitory promiscuity	-	0.9408	94.08%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5620	56.20%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.6666	66.66%
Skin irritation	+	0.5780	57.80%
Skin corrosion	-	0.9133	91.33%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5501	55.01%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.7060	70.60%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.7281	72.81%
Acute Oral Toxicity (c)	III	0.4789	47.89%
Estrogen receptor binding	-	0.5096	50.96%
Androgen receptor binding	+	0.5696	56.96%
Thyroid receptor binding	+	0.5437	54.37%
Glucocorticoid receptor binding	-	0.5580	55.80%
Aromatase binding	-	0.5729	57.29%
PPAR gamma	-	0.6492	64.92%
Honey bee toxicity	-	0.8375	83.75%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	92.13%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.21%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.95%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.42%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.36%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.43%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.25%	85.14%
CHEMBL1871	P10275	Androgen Receptor	82.59%	96.43%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.37%	93.03%
CHEMBL259	P32245	Melanocortin receptor 4	81.35%	95.38%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.25%	90.08%

Plants that contains it

• Cichorium pumilum

Cross-Links

• PubChem: 163094316
• LOTUS: LTS0108467
• wikiData: Q105113534