(3aR,5R,5aS,6S,8aR,9R,9aS)-6,9-dihydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione

Details

• Internal ID: 01d052f2-493e-41bd-b781-4da39fce2e07
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (3aR,5R,5aS,6S,8aR,9R,9aS)-6,9-dihydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
• InChI: InChI=1S/C15H20O5/c1-6-4-9-11(7(2)14(19)20-9)13(18)15(3)10(17)5-8(16)12(6)15/h6,8-9,11-13,16,18H,2,4-5H2,1,3H3/t6-,8+,9-,11-,12-,13-,15-/m1/s1
• InChI Key: QWAHSQZRRHWBIQ-SAVQYEBCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.44
• 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	+	0.9754	97.54%
Caco-2	-	0.6067	60.67%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4945	49.45%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8924	89.24%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9614	96.14%
P-glycoprotein inhibitior	-	0.9198	91.98%
P-glycoprotein substrate	-	0.8216	82.16%
CYP3A4 substrate	+	0.5709	57.09%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.8062	80.62%
CYP2C9 inhibition	-	0.8811	88.11%
CYP2C19 inhibition	-	0.8896	88.96%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.6779	67.79%
CYP2C8 inhibition	-	0.8627	86.27%
CYP inhibitory promiscuity	-	0.9566	95.66%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5091	50.91%
Eye corrosion	-	0.9810	98.10%
Eye irritation	-	0.8750	87.50%
Skin irritation	+	0.5143	51.43%
Skin corrosion	-	0.8385	83.85%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7668	76.68%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.8337	83.37%
skin sensitisation	-	0.7130	71.30%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.7841	78.41%
Acute Oral Toxicity (c)	II	0.4927	49.27%
Estrogen receptor binding	+	0.7285	72.85%
Androgen receptor binding	+	0.5342	53.42%
Thyroid receptor binding	-	0.6045	60.45%
Glucocorticoid receptor binding	-	0.5235	52.35%
Aromatase binding	-	0.6105	61.05%
PPAR gamma	-	0.6102	61.02%
Honey bee toxicity	-	0.7896	78.96%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.96%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.55%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.80%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.55%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.08%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	84.89%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	83.73%	97.79%

Plants that contains it

• Haplophyllum tenue
• Teucrium divaricatum

Cross-Links

• PubChem: 101529190
• LOTUS: LTS0043998
• wikiData: Q104396415