(3aS,6aS,9R,9aR,9bS)-3a-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 5ec781ca-8991-44f8-96fb-864cfa8d3823
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aS,9R,9aR,9bS)-3a-hydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1CCC2C1C3C(CCC2=C)(C(=C)C(=O)O3)O
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@@H]1[C@H]3[C@](CCC2=C)(C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H20O3/c1-8-6-7-15(17)10(3)14(16)18-13(15)12-9(2)4-5-11(8)12/h9,11-13,17H,1,3-7H2,2H3/t9-,11-,12-,13+,15+/m1/s1
• InChI Key: SCFHNGVHFGOVGF-VEPFAGFCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.21
• 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	+	0.9947	99.47%
Caco-2	+	0.6869	68.69%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5830	58.30%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.9551	95.51%
P-glycoprotein inhibitior	-	0.9117	91.17%
P-glycoprotein substrate	-	0.8822	88.22%
CYP3A4 substrate	+	0.5817	58.17%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8572	85.72%
CYP3A4 inhibition	-	0.8326	83.26%
CYP2C9 inhibition	-	0.8679	86.79%
CYP2C19 inhibition	-	0.7280	72.80%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	+	0.6727	67.27%
CYP2C8 inhibition	-	0.8821	88.21%
CYP inhibitory promiscuity	-	0.9714	97.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5129	51.29%
Eye corrosion	-	0.9728	97.28%
Eye irritation	+	0.6093	60.93%
Skin irritation	+	0.5425	54.25%
Skin corrosion	-	0.8759	87.59%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4844	48.44%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.7408	74.08%
skin sensitisation	-	0.7256	72.56%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4623	46.23%
Acute Oral Toxicity (c)	IV	0.3886	38.86%
Estrogen receptor binding	+	0.6784	67.84%
Androgen receptor binding	+	0.5672	56.72%
Thyroid receptor binding	-	0.5508	55.08%
Glucocorticoid receptor binding	+	0.6555	65.55%
Aromatase binding	-	0.6025	60.25%
PPAR gamma	-	0.6920	69.20%
Honey bee toxicity	-	0.9273	92.73%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9690	96.90%

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	95.76%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.65%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.46%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.66%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.16%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.71%	93.04%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.61%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.12%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.99%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.45%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.01%	96.09%

Plants that contains it

• Decachaeta ovatifolia

Cross-Links

• PubChem: 162886182
• LOTUS: LTS0071792
• wikiData: Q105250083