(3S,3aS,6aR,9aR,9bS)-3-(methoxymethyl)-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

• Internal ID: c86fda49-20e0-429d-8fdf-ae33bd0b6ff4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,6aR,9aR,9bS)-3-(methoxymethyl)-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): COCC1C2CCC(=C)C3CCC(=C)C3C2OC1=O
• SMILES (Isomeric): COC[C@@H]1[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O
• InChI: InChI=1S/C16H22O3/c1-9-4-7-12-13(8-18-3)16(17)19-15(12)14-10(2)5-6-11(9)14/h11-15H,1-2,4-8H2,3H3/t11-,12-,13+,14-,15-/m0/s1
• InChI Key: ZNXSOKHFOMIGLF-RMEBNNNOSA-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): 35.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.72
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.7104	71.04%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5256	52.56%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.7343	73.43%
P-glycoprotein inhibitior	-	0.8447	84.47%
P-glycoprotein substrate	-	0.8374	83.74%
CYP3A4 substrate	+	0.5876	58.76%
CYP2C9 substrate	+	0.5981	59.81%
CYP2D6 substrate	-	0.8098	80.98%
CYP3A4 inhibition	-	0.8468	84.68%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.6219	62.19%
CYP2D6 inhibition	-	0.8796	87.96%
CYP1A2 inhibition	+	0.5728	57.28%
CYP2C8 inhibition	-	0.8694	86.94%
CYP inhibitory promiscuity	-	0.7285	72.85%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6122	61.22%
Eye corrosion	-	0.8772	87.72%
Eye irritation	+	0.8069	80.69%
Skin irritation	-	0.7240	72.40%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7527	75.27%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	-	0.6178	61.78%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5547	55.47%
Acute Oral Toxicity (c)	III	0.4775	47.75%
Estrogen receptor binding	-	0.6606	66.06%
Androgen receptor binding	+	0.6575	65.75%
Thyroid receptor binding	-	0.6152	61.52%
Glucocorticoid receptor binding	+	0.6494	64.94%
Aromatase binding	-	0.7801	78.01%
PPAR gamma	-	0.7831	78.31%
Honey bee toxicity	-	0.8026	80.26%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
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
CHEMBL3137262	O60341	LSD1/CoREST complex	92.46%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.15%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.45%	97.25%
CHEMBL1871	P10275	Androgen Receptor	87.96%	96.43%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.42%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.79%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.22%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.09%	95.56%
CHEMBL5957	P21589	5'-nucleotidase	80.90%	97.78%
CHEMBL2581	P07339	Cathepsin D	80.07%	98.95%

Plants that contains it

• Aconitum soongaricum
• Aucklandia costus

Cross-Links

• PubChem: 15894247
• LOTUS: LTS0251355
• wikiData: Q105342382