(3aS,6S,6aS,9S,9aR,9bR)-9-hydroxy-9a-(hydroxymethyl)-6-methyl-3-methylidene-4,5,6,6a,7,8,9,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: f820c7f5-8c7a-472b-b3b6-afb581ee6885
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aS,6S,6aS,9S,9aR,9bR)-9-hydroxy-9a-(hydroxymethyl)-6-methyl-3-methylidene-4,5,6,6a,7,8,9,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• InChI: InChI=1S/C15H22O4/c1-8-3-4-10-9(2)14(18)19-13(10)15(7-16)11(8)5-6-12(15)17/h8,10-13,16-17H,2-7H2,1H3/t8-,10-,11-,12-,13+,15-/m0/s1
• InChI Key: WHRVEOYAUAOADS-PCKATOIHSA-N
• Popularity: 2 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): 66.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9586	95.86%
Caco-2	+	0.5109	51.09%
Blood Brain Barrier	+	0.5027	50.27%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5419	54.19%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.9024	90.24%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.5781	57.81%
BSEP inhibitior	-	0.9323	93.23%
P-glycoprotein inhibitior	-	0.9124	91.24%
P-glycoprotein substrate	-	0.7937	79.37%
CYP3A4 substrate	+	0.6015	60.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8459	84.59%
CYP3A4 inhibition	-	0.8701	87.01%
CYP2C9 inhibition	-	0.8237	82.37%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.6935	69.35%
CYP2C8 inhibition	-	0.8393	83.93%
CYP inhibitory promiscuity	-	0.9142	91.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6275	62.75%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.7563	75.63%
Skin irritation	-	0.5539	55.39%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7783	77.83%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6343	63.43%
skin sensitisation	-	0.8682	86.82%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5253	52.53%
Acute Oral Toxicity (c)	III	0.5038	50.38%
Estrogen receptor binding	+	0.6012	60.12%
Androgen receptor binding	+	0.6180	61.80%
Thyroid receptor binding	-	0.5594	55.94%
Glucocorticoid receptor binding	+	0.6935	69.35%
Aromatase binding	-	0.6017	60.17%
PPAR gamma	-	0.6303	63.03%
Honey bee toxicity	-	0.8978	89.78%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9625	96.25%

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	96.25%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.55%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.80%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.99%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.73%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.88%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	86.85%	95.93%
CHEMBL2581	P07339	Cathepsin D	85.24%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	83.19%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.56%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.15%	94.45%

Plants that contains it

• Rudbeckia grandiflora

Cross-Links

• PubChem: 14137522
• LOTUS: LTS0096385
• wikiData: Q105305771