(3S,3aS,6S,6aR,9aR,9bS)-3,9-dimethyl-2,7-dioxo-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-6-carbaldehyde

Details

• Internal ID: 0ae2ec46-80a3-493a-9cd1-1f375fdeae52
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,6S,6aR,9aR,9bS)-3,9-dimethyl-2,7-dioxo-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-6-carbaldehyde
• SMILES (Canonical): CC1C2CCC(C3C(C2OC1=O)C(=CC3=O)C)C=O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@H]([C@H]3[C@@H]([C@H]2OC1=O)C(=CC3=O)C)C=O
• InChI: InChI=1S/C15H18O4/c1-7-5-11(17)13-9(6-16)3-4-10-8(2)15(18)19-14(10)12(7)13/h5-6,8-10,12-14H,3-4H2,1-2H3/t8-,9+,10-,12-,13+,14-/m0/s1
• InChI Key: QLRPWTNTDHAWJM-LIHSWJCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.5779	57.79%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5333	53.33%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9225	92.25%
P-glycoprotein inhibitior	-	0.8881	88.81%
P-glycoprotein substrate	-	0.7377	73.77%
CYP3A4 substrate	+	0.5321	53.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8952	89.52%
CYP3A4 inhibition	-	0.9154	91.54%
CYP2C9 inhibition	-	0.9094	90.94%
CYP2C19 inhibition	-	0.8680	86.80%
CYP2D6 inhibition	-	0.8970	89.70%
CYP1A2 inhibition	+	0.7215	72.15%
CYP2C8 inhibition	-	0.9146	91.46%
CYP inhibitory promiscuity	-	0.8564	85.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9725	97.25%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9026	90.26%
Eye irritation	-	0.7580	75.80%
Skin irritation	+	0.5216	52.16%
Skin corrosion	-	0.7464	74.64%
Ames mutagenesis	-	0.7737	77.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4359	43.59%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.8283	82.83%
skin sensitisation	-	0.6510	65.10%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5620	56.20%
Acute Oral Toxicity (c)	III	0.6034	60.34%
Estrogen receptor binding	+	0.5999	59.99%
Androgen receptor binding	+	0.5717	57.17%
Thyroid receptor binding	-	0.7343	73.43%
Glucocorticoid receptor binding	-	0.6098	60.98%
Aromatase binding	-	0.8076	80.76%
PPAR gamma	-	0.7276	72.76%
Honey bee toxicity	-	0.8059	80.59%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9498	94.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.20%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.51%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	91.64%	86.00%
CHEMBL1871	P10275	Androgen Receptor	88.15%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.02%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.05%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.65%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.88%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.46%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	82.17%	91.49%
CHEMBL2581	P07339	Cathepsin D	81.13%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	80.20%	94.73%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.08%	93.04%

Plants that contains it

• Artemisia reptans

Cross-Links

• PubChem: 101675249
• LOTUS: LTS0107128
• wikiData: Q105223741