(3S,3aS,6R,6aR,9aR,9bR)-6-hydroxy-3,6,9a-trimethyl-3,3a,4,5,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione

Details

• Internal ID: 6bd03e4a-eda2-48bf-a64d-d7a043a427aa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3S,3aS,6R,6aR,9aR,9bR)-6-hydroxy-3,6,9a-trimethyl-3,3a,4,5,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1C2CCC(C3CCC(=O)C3(C2OC1=O)C)(C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]([C@@H]3CCC(=O)[C@]3([C@@H]2OC1=O)C)(C)O
• InChI: InChI=1S/C15H22O4/c1-8-9-6-7-14(2,18)10-4-5-11(16)15(10,3)12(9)19-13(8)17/h8-10,12,18H,4-7H2,1-3H3/t8-,9-,10-,12+,14+,15-/m0/s1
• InChI Key: IUUCPMXTYQHRQG-PKEXYXDBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 4
• 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	+	0.9673	96.73%
Caco-2	+	0.6494	64.94%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6161	61.61%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9114	91.14%
OATP1B3 inhibitior	+	0.9018	90.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.9137	91.37%
P-glycoprotein inhibitior	-	0.8765	87.65%
P-glycoprotein substrate	-	0.8729	87.29%
CYP3A4 substrate	+	0.5838	58.38%
CYP2C9 substrate	-	0.8104	81.04%
CYP2D6 substrate	-	0.8535	85.35%
CYP3A4 inhibition	-	0.8275	82.75%
CYP2C9 inhibition	-	0.8319	83.19%
CYP2C19 inhibition	-	0.8425	84.25%
CYP2D6 inhibition	-	0.9732	97.32%
CYP1A2 inhibition	-	0.5540	55.40%
CYP2C8 inhibition	-	0.9203	92.03%
CYP inhibitory promiscuity	-	0.9935	99.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6619	66.19%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9123	91.23%
Skin irritation	+	0.5521	55.21%
Skin corrosion	-	0.7884	78.84%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8562	85.62%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.6408	64.08%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5170	51.70%
Acute Oral Toxicity (c)	II	0.4412	44.12%
Estrogen receptor binding	+	0.6356	63.56%
Androgen receptor binding	+	0.5410	54.10%
Thyroid receptor binding	-	0.5863	58.63%
Glucocorticoid receptor binding	+	0.5578	55.78%
Aromatase binding	-	0.7131	71.31%
PPAR gamma	-	0.6558	65.58%
Honey bee toxicity	-	0.9081	90.81%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9322	93.22%

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	95.45%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.52%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.00%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.06%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.95%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.79%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.26%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.86%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.19%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.17%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	82.40%	94.75%

Plants that contains it

• Ambrosia ambrosioides

Cross-Links

• PubChem: 162846364
• LOTUS: LTS0252012
• wikiData: Q105120832