(3aS,5aS,8R,8aR,9aR)-8-methyl-1,2,5-trimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-ol

Details

• Internal ID: 597e8069-5ab0-467d-a0d1-4dfd5bf05d19
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (3aS,5aS,8R,8aR,9aR)-8-methyl-1,2,5-trimethylidene-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-ol
• SMILES (Canonical): CC1(CCC2C1CC3C(CC2=C)OC(=C)C3=C)O
• SMILES (Isomeric): C[C@]1(CC[C@H]2[C@H]1C[C@H]3[C@H](CC2=C)OC(=C)C3=C)O
• InChI: InChI=1S/C16H22O2/c1-9-7-15-13(10(2)11(3)18-15)8-14-12(9)5-6-16(14,4)17/h12-15,17H,1-3,5-8H2,4H3/t12-,13-,14-,15+,16-/m1/s1
• InChI Key: KWWMYEJFOYMMQP-DGXTUMSLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₂
• Molecular Weight: 246.34 g/mol
• Exact Mass: 246.161979940 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 2
• 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	+	0.9953	99.53%
Caco-2	+	0.5636	56.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5492	54.92%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.8650	86.50%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9719	97.19%
P-glycoprotein inhibitior	-	0.9105	91.05%
P-glycoprotein substrate	-	0.8030	80.30%
CYP3A4 substrate	+	0.6255	62.55%
CYP2C9 substrate	-	0.7825	78.25%
CYP2D6 substrate	-	0.7801	78.01%
CYP3A4 inhibition	-	0.8196	81.96%
CYP2C9 inhibition	-	0.8219	82.19%
CYP2C19 inhibition	-	0.5196	51.96%
CYP2D6 inhibition	-	0.9405	94.05%
CYP1A2 inhibition	+	0.6532	65.32%
CYP2C8 inhibition	-	0.6857	68.57%
CYP inhibitory promiscuity	-	0.8603	86.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4705	47.05%
Eye corrosion	-	0.9714	97.14%
Eye irritation	-	0.6037	60.37%
Skin irritation	+	0.5060	50.60%
Skin corrosion	-	0.9099	90.99%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4845	48.45%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.7534	75.34%
skin sensitisation	-	0.6098	60.98%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6900	69.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5978	59.78%
Acute Oral Toxicity (c)	III	0.6009	60.09%
Estrogen receptor binding	+	0.6891	68.91%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8173	81.73%
Aromatase binding	-	0.6061	60.61%
PPAR gamma	-	0.5817	58.17%
Honey bee toxicity	-	0.8282	82.82%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9336	93.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	92.62%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.60%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.42%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	90.72%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.58%	96.09%
CHEMBL206	P03372	Estrogen receptor alpha	88.48%	97.64%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.25%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.65%	89.05%
CHEMBL242	Q92731	Estrogen receptor beta	84.79%	98.35%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.92%	85.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.41%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.81%	92.94%
CHEMBL217	P14416	Dopamine D2 receptor	81.69%	95.62%
CHEMBL226	P30542	Adenosine A1 receptor	80.63%	95.93%

Plants that contains it

• Inula racemosa

Cross-Links

• PubChem: 162842791
• LOTUS: LTS0167922
• wikiData: Q105147188