(6S,6aS,9aR,9bR)-3-(hydroxymethyl)-6,9a-dimethyl-5,6,6a,7,8,9b-hexahydro-4H-azuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: 1eaa358c-63ec-4efb-8d83-7b65ec9bf7f6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (6S,6aS,9aR,9bR)-3-(hydroxymethyl)-6,9a-dimethyl-5,6,6a,7,8,9b-hexahydro-4H-azuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1CCC2=C(C(=O)OC2C3(C1CCC3=O)C)CO
• SMILES (Isomeric): C[C@H]1CCC2=C(C(=O)O[C@H]2[C@]3([C@H]1CCC3=O)C)CO
• InChI: InChI=1S/C15H20O4/c1-8-3-4-9-10(7-16)14(18)19-13(9)15(2)11(8)5-6-12(15)17/h8,11,13,16H,3-7H2,1-2H3/t8-,11-,13+,15-/m0/s1
• InChI Key: SQBLZGPDZBFVEE-BUWBAVOPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.62
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9758	97.58%
Caco-2	+	0.7714	77.14%
Blood Brain Barrier	+	0.7619	76.19%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7548	75.48%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.8727	87.27%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	+	0.6162	61.62%
BSEP inhibitior	-	0.8787	87.87%
P-glycoprotein inhibitior	-	0.8584	85.84%
P-glycoprotein substrate	-	0.8978	89.78%
CYP3A4 substrate	+	0.5767	57.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9084	90.84%
CYP3A4 inhibition	-	0.7721	77.21%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.9079	90.79%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.8663	86.63%
CYP inhibitory promiscuity	-	0.9392	93.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5303	53.03%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.8737	87.37%
Skin irritation	+	0.5521	55.21%
Skin corrosion	-	0.9150	91.50%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6176	61.76%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5386	53.86%
skin sensitisation	-	0.8853	88.53%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4814	48.14%
Acute Oral Toxicity (c)	III	0.5172	51.72%
Estrogen receptor binding	+	0.5603	56.03%
Androgen receptor binding	+	0.5895	58.95%
Thyroid receptor binding	-	0.5348	53.48%
Glucocorticoid receptor binding	+	0.6454	64.54%
Aromatase binding	-	0.6321	63.21%
PPAR gamma	+	0.5191	51.91%
Honey bee toxicity	-	0.9322	93.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9724	97.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.42%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.03%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.61%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.20%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.20%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.47%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.35%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.93%	86.33%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.25%	90.08%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.11%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	80.99%	97.79%

Plants that contains it

• Ambrosia artemisiifolia

Cross-Links

• PubChem: 162968824
• LOTUS: LTS0052154
• wikiData: Q105257748