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

Details

• Internal ID: 8e025d5a-f32a-4fd8-88d0-7cf090bbeb22
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (3aR,5R,8aR,9S,9aR)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,7,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
• InChI: InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4,7,10,12-13,17H,2,5-6H2,1,3H3/t7-,10-,12+,13+,15+/m1/s1
• InChI Key: XYORYLFXKGELIL-LCVJNDBOSA-N
• Popularity: 2 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): 63.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.39
• 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	+	0.9812	98.12%
Caco-2	-	0.5395	53.95%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5860	58.60%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9086	90.86%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9321	93.21%
P-glycoprotein inhibitior	-	0.8976	89.76%
P-glycoprotein substrate	-	0.8450	84.50%
CYP3A4 substrate	+	0.5515	55.15%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.8163	81.63%
CYP2C9 inhibition	-	0.8564	85.64%
CYP2C19 inhibition	-	0.8806	88.06%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	+	0.5294	52.94%
CYP2C8 inhibition	-	0.8141	81.41%
CYP inhibitory promiscuity	-	0.9534	95.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5122	51.22%
Eye corrosion	-	0.9747	97.47%
Eye irritation	-	0.9072	90.72%
Skin irritation	+	0.5249	52.49%
Skin corrosion	-	0.8313	83.13%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6869	68.69%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.7030	70.30%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7326	73.26%
Acute Oral Toxicity (c)	II	0.6120	61.20%
Estrogen receptor binding	+	0.5584	55.84%
Androgen receptor binding	+	0.5521	55.21%
Thyroid receptor binding	-	0.5919	59.19%
Glucocorticoid receptor binding	-	0.5130	51.30%
Aromatase binding	-	0.6395	63.95%
PPAR gamma	-	0.5990	59.90%
Honey bee toxicity	-	0.8093	80.93%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9882	98.82%

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	95.13%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.58%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.63%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.93%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.69%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.97%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.02%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.83%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.82%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.61%	90.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.35%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.21%	94.45%

Plants that contains it

• Helenium mexicanum

Cross-Links

• PubChem: 162857500
• LOTUS: LTS0238948
• wikiData: Q105344594