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

Details

• Internal ID: d99cf9aa-28a0-4bc2-a67a-dec8da116376
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3S,3aS,6R,6aS,9aS,9bR)-6,6a-dihydroxy-3,6,9a-trimethyl-3a,4,5,7,8,9b-hexahydro-3H-azuleno[8,7-b]furan-2,9-dione
• SMILES (Canonical): CC1C2CCC(C3(CCC(=O)C3(C2OC1=O)C)O)(C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]([C@@]3(CCC(=O)[C@]3([C@@H]2OC1=O)C)O)(C)O
• InChI: InChI=1S/C15H22O5/c1-8-9-4-6-13(2,18)15(19)7-5-10(16)14(15,3)11(9)20-12(8)17/h8-9,11,18-19H,4-7H2,1-3H3/t8-,9-,11+,13+,14-,15+/m0/s1
• InChI Key: JETUWSFHFWWQGP-NHQBGTEVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.81
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8967	89.67%
Caco-2	+	0.5070	50.70%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6308	63.08%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.9398	93.98%
OATP1B3 inhibitior	+	0.9152	91.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8571	85.71%
BSEP inhibitior	-	0.8627	86.27%
P-glycoprotein inhibitior	-	0.8885	88.85%
P-glycoprotein substrate	-	0.8640	86.40%
CYP3A4 substrate	+	0.6112	61.12%
CYP2C9 substrate	-	0.8084	80.84%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.7171	71.71%
CYP2C9 inhibition	-	0.8011	80.11%
CYP2C19 inhibition	-	0.6933	69.33%
CYP2D6 inhibition	-	0.9681	96.81%
CYP1A2 inhibition	+	0.5435	54.35%
CYP2C8 inhibition	-	0.9591	95.91%
CYP inhibitory promiscuity	-	0.9947	99.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6282	62.82%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9171	91.71%
Skin irritation	+	0.5149	51.49%
Skin corrosion	-	0.8442	84.42%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8605	86.05%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8772	87.72%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5924	59.24%
Acute Oral Toxicity (c)	III	0.3009	30.09%
Estrogen receptor binding	+	0.7674	76.74%
Androgen receptor binding	+	0.6651	66.51%
Thyroid receptor binding	+	0.5317	53.17%
Glucocorticoid receptor binding	+	0.5947	59.47%
Aromatase binding	-	0.5500	55.00%
PPAR gamma	-	0.6569	65.69%
Honey bee toxicity	-	0.9122	91.22%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9269	92.69%

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	94.26%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.09%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.44%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.31%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.40%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.44%	94.75%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.30%	98.46%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.16%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.01%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.07%	96.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.38%	92.94%

Plants that contains it

• Parthenium hysterophorus

Cross-Links

• PubChem: 12115381
• LOTUS: LTS0242159
• wikiData: Q105126396