(1R,3S,5S,5aS,7S,9R,9aS,9bR)-1,3,5-trimethoxy-7,9a-dimethyl-6-methylidene-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-ol

Details

• Internal ID: 4a622073-fb76-4aab-a24f-cc93a11715f5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,3S,5S,5aS,7S,9R,9aS,9bR)-1,3,5-trimethoxy-7,9a-dimethyl-6-methylidene-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-ol
• SMILES (Canonical): CC1CC(C2(C(C1=C)C(C=C3C2C(OC3OC)OC)OC)C)O
• SMILES (Isomeric): C[C@H]1C[C@H]([C@]2([C@H](C1=C)[C@H](C=C3[C@@H]2[C@@H](O[C@@H]3OC)OC)OC)C)O
• InChI: InChI=1S/C18H28O5/c1-9-7-13(19)18(3)14(10(9)2)12(20-4)8-11-15(18)17(22-6)23-16(11)21-5/h8-9,12-17,19H,2,7H2,1,3-6H3/t9-,12-,13+,14+,15+,16-,17+,18-/m0/s1
• InChI Key: WWKLNYZIVVPDBN-JOLFBPBZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.19367399 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.11
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.5277	52.77%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4127	41.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9048	90.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7702	77.02%
P-glycoprotein inhibitior	-	0.7930	79.30%
P-glycoprotein substrate	-	0.7615	76.15%
CYP3A4 substrate	+	0.6493	64.93%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7833	78.33%
CYP3A4 inhibition	-	0.5775	57.75%
CYP2C9 inhibition	-	0.8868	88.68%
CYP2C19 inhibition	-	0.8421	84.21%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.6860	68.60%
CYP2C8 inhibition	-	0.6688	66.88%
CYP inhibitory promiscuity	-	0.7658	76.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9208	92.08%
Carcinogenicity (trinary)	Non-required	0.4283	42.83%
Eye corrosion	-	0.9833	98.33%
Eye irritation	-	0.8991	89.91%
Skin irritation	-	0.6117	61.17%
Skin corrosion	-	0.9345	93.45%
Ames mutagenesis	-	0.5718	57.18%
Human Ether-a-go-go-Related Gene inhibition	-	0.4612	46.12%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.7135	71.35%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5559	55.59%
Acute Oral Toxicity (c)	III	0.3864	38.64%
Estrogen receptor binding	+	0.6298	62.98%
Androgen receptor binding	+	0.5667	56.67%
Thyroid receptor binding	+	0.6861	68.61%
Glucocorticoid receptor binding	+	0.6089	60.89%
Aromatase binding	-	0.5230	52.30%
PPAR gamma	+	0.5821	58.21%
Honey bee toxicity	-	0.6771	67.71%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9596	95.96%

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	95.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.59%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.20%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.40%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.77%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.12%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.63%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.50%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.21%	91.07%

Plants that contains it

• Pseudowintera axillaris

Cross-Links

• PubChem: 11551567
• LOTUS: LTS0166787
• wikiData: Q105314112