(1S,3aR,5R,5aS,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,7-b]furan-2,8-dione

Details

• Internal ID: 255387b6-7a7e-410c-8b05-8744fc6d638e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (1S,3aR,5R,5aS,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,7-b]furan-2,8-dione
• InChI: InChI=1S/C15H22O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h7-10,12-13,17H,4-6H2,1-3H3/t7-,8+,9+,10-,12-,13+,15+/m1/s1
• InChI Key: LWZYMGJOEZRREO-ZIXXKTFOSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 2,3,11,13-Tetrahydrohelenalin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9406	94.06%
Caco-2	+	0.6632	66.32%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6181	61.81%
OATP2B1 inhibitior	-	0.8508	85.08%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9007	90.07%
P-glycoprotein inhibitior	-	0.8813	88.13%
P-glycoprotein substrate	-	0.8484	84.84%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8269	82.69%
CYP3A4 inhibition	-	0.8892	88.92%
CYP2C9 inhibition	-	0.8691	86.91%
CYP2C19 inhibition	-	0.8947	89.47%
CYP2D6 inhibition	-	0.9700	97.00%
CYP1A2 inhibition	+	0.5227	52.27%
CYP2C8 inhibition	-	0.8931	89.31%
CYP inhibitory promiscuity	-	0.9918	99.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6688	66.88%
Eye corrosion	-	0.9760	97.60%
Eye irritation	-	0.9320	93.20%
Skin irritation	+	0.5447	54.47%
Skin corrosion	-	0.7239	72.39%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5838	58.38%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.8243	82.43%
skin sensitisation	-	0.8697	86.97%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5270	52.70%
Acute Oral Toxicity (c)	II	0.4347	43.47%
Estrogen receptor binding	+	0.6780	67.80%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5093	50.93%
Glucocorticoid receptor binding	-	0.6466	64.66%
Aromatase binding	-	0.8200	82.00%
PPAR gamma	-	0.6875	68.75%
Honey bee toxicity	-	0.8796	87.96%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9445	94.45%

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	95.20%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.07%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.56%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.62%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.21%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.70%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.70%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.70%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.82%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	83.17%	97.79%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.74%	93.04%
CHEMBL1871	P10275	Androgen Receptor	80.44%	96.43%

Plants that contains it

• Arnica montana

Cross-Links

• PubChem: 21723763
• LOTUS: LTS0025358
• wikiData: Q105158701