[(3S,3aR,4S,6aR,9S,9aR,9bR)-3,9-dimethyl-6-methylidene-2,8-dioxo-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] acetate

Details

• Internal ID: 767b5920-8634-4f52-af22-5d2ca3d1bd70
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3S,3aR,4S,6aR,9S,9aR,9bR)-3,9-dimethyl-6-methylidene-2,8-dioxo-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)[C@H]3C)OC(=O)C
• InChI: InChI=1S/C17H22O5/c1-7-5-13(21-10(4)18)15-9(3)17(20)22-16(15)14-8(2)12(19)6-11(7)14/h8-9,11,13-16H,1,5-6H2,2-4H3/t8-,9+,11+,13+,14+,15-,16-/m1/s1
• InChI Key: QBXGUKUDRCWSKF-KNFRCYCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 5
• 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	+	0.9907	99.07%
Caco-2	+	0.7278	72.78%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5256	52.56%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8865	88.65%
OATP1B3 inhibitior	+	0.9022	90.22%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7124	71.24%
P-glycoprotein inhibitior	-	0.6683	66.83%
P-glycoprotein substrate	-	0.8246	82.46%
CYP3A4 substrate	+	0.5659	56.59%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.5695	56.95%
CYP2C9 inhibition	-	0.8810	88.10%
CYP2C19 inhibition	-	0.7805	78.05%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.5479	54.79%
CYP2C8 inhibition	-	0.9307	93.07%
CYP inhibitory promiscuity	-	0.8464	84.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9225	92.25%
Carcinogenicity (trinary)	Non-required	0.5999	59.99%
Eye corrosion	-	0.9308	93.08%
Eye irritation	-	0.5403	54.03%
Skin irritation	-	0.6286	62.86%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4004	40.04%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.7002	70.02%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6219	62.19%
Acute Oral Toxicity (c)	II	0.4497	44.97%
Estrogen receptor binding	+	0.6539	65.39%
Androgen receptor binding	+	0.5228	52.28%
Thyroid receptor binding	-	0.5622	56.22%
Glucocorticoid receptor binding	-	0.5474	54.74%
Aromatase binding	-	0.5987	59.87%
PPAR gamma	-	0.8423	84.23%
Honey bee toxicity	-	0.7546	75.46%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9884	98.84%

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	93.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.08%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.47%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.10%	85.14%
CHEMBL2581	P07339	Cathepsin D	85.92%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162996209
• LOTUS: LTS0257147
• wikiData: Q105218058