8-Hydroxy-8a-(hydroxymethyl)-1,5-dimethyl-1,3a,4,5,5a,6,7,8,9,9a-decahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 03324285-9a8b-47af-87b6-6f55496f7914
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: 8-hydroxy-8a-(hydroxymethyl)-1,5-dimethyl-1,3a,4,5,5a,6,7,8,9,9a-decahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC3(C1CCC3O)CO)C(C(=O)O2)C
• SMILES (Isomeric): CC1CC2C(CC3(C1CCC3O)CO)C(C(=O)O2)C
• InChI: InChI=1S/C15H24O4/c1-8-5-12-10(9(2)14(18)19-12)6-15(7-16)11(8)3-4-13(15)17/h8-13,16-17H,3-7H2,1-2H3
• InChI Key: RYOFDYNDVUYAIE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.34
• 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	+	0.9211	92.11%
Caco-2	+	0.7146	71.46%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5560	55.60%
OATP2B1 inhibitior	-	0.8507	85.07%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6961	69.61%
BSEP inhibitior	-	0.8651	86.51%
P-glycoprotein inhibitior	-	0.9305	93.05%
P-glycoprotein substrate	-	0.6669	66.69%
CYP3A4 substrate	+	0.6371	63.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8342	83.42%
CYP3A4 inhibition	-	0.8363	83.63%
CYP2C9 inhibition	-	0.8437	84.37%
CYP2C19 inhibition	-	0.8951	89.51%
CYP2D6 inhibition	-	0.9553	95.53%
CYP1A2 inhibition	-	0.7715	77.15%
CYP2C8 inhibition	-	0.8934	89.34%
CYP inhibitory promiscuity	-	0.9627	96.27%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7018	70.18%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9242	92.42%
Skin irritation	-	0.6409	64.09%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5904	59.04%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.9131	91.31%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5541	55.41%
Acute Oral Toxicity (c)	III	0.4699	46.99%
Estrogen receptor binding	+	0.6507	65.07%
Androgen receptor binding	-	0.5065	50.65%
Thyroid receptor binding	+	0.6761	67.61%
Glucocorticoid receptor binding	+	0.7429	74.29%
Aromatase binding	-	0.6386	63.86%
PPAR gamma	-	0.6255	62.55%
Honey bee toxicity	-	0.8383	83.83%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8158	81.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.06%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.68%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.59%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.40%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.47%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.38%	94.80%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.35%	96.95%
CHEMBL299	P17252	Protein kinase C alpha	87.23%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.06%	95.56%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	85.70%	98.46%
CHEMBL226	P30542	Adenosine A1 receptor	85.64%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.85%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.39%	94.45%

Plants that contains it

• Humulus lupulus
• Rudbeckia mollis

Cross-Links

• PubChem: 162997112
• LOTUS: LTS0121731
• wikiData: Q105248889