(3aS,5S,6aR,9aR,9bS)-5-hydroxy-3,6,9-trimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: b0f58e30-b562-4e38-98d6-e323599258cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5S,6aR,9aR,9bS)-5-hydroxy-3,6,9-trimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): C=C1C2CC(C(=C)C3CC(=O)C(=C)C3C2OC1=O)O
• SMILES (Isomeric): C=C1[C@@H]2C[C@@H](C(=C)[C@@H]3CC(=O)C(=C)[C@@H]3[C@H]2OC1=O)O
• InChI: InChI=1S/C15H16O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h9-11,13-14,16H,1-5H2/t9-,10-,11-,13-,14-/m0/s1
• InChI Key: OPCVSKQBBWXUMQ-GRLWGSQLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.17
• 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	+	0.9784	97.84%
Caco-2	-	0.6507	65.07%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5781	57.81%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9112	91.12%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9433	94.33%
P-glycoprotein inhibitior	-	0.9269	92.69%
P-glycoprotein substrate	-	0.8577	85.77%
CYP3A4 substrate	-	0.5387	53.87%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8419	84.19%
CYP3A4 inhibition	-	0.9194	91.94%
CYP2C9 inhibition	-	0.9088	90.88%
CYP2C19 inhibition	-	0.8803	88.03%
CYP2D6 inhibition	-	0.9280	92.80%
CYP1A2 inhibition	-	0.8567	85.67%
CYP2C8 inhibition	-	0.8902	89.02%
CYP inhibitory promiscuity	-	0.9650	96.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9142	91.42%
Carcinogenicity (trinary)	Non-required	0.5861	58.61%
Eye corrosion	-	0.8926	89.26%
Eye irritation	+	0.7499	74.99%
Skin irritation	-	0.5686	56.86%
Skin corrosion	-	0.8676	86.76%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7378	73.78%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	-	0.6848	68.48%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7352	73.52%
Acute Oral Toxicity (c)	III	0.3982	39.82%
Estrogen receptor binding	+	0.5459	54.59%
Androgen receptor binding	+	0.5413	54.13%
Thyroid receptor binding	-	0.6516	65.16%
Glucocorticoid receptor binding	+	0.5971	59.71%
Aromatase binding	-	0.7692	76.92%
PPAR gamma	-	0.7316	73.16%
Honey bee toxicity	-	0.5856	58.56%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9167	91.67%

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	93.56%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.10%	97.09%
CHEMBL308	P06493	Cyclin-dependent kinase 1	88.48%	91.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.06%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.77%	99.23%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.45%	96.00%

Plants that contains it

• Cyrtocymura scorpioides

Cross-Links

• PubChem: 162907217
• LOTUS: LTS0045557
• wikiData: Q105195976