(Z)-2-[2-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]but-2-ene-1,4-diol

Details

• Internal ID: 72cffb83-82c9-4afd-8bff-8f32a08de1e4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-2-[2-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl]but-2-ene-1,4-diol
• SMILES (Canonical): CC1(CCCC2(C1CC=C(C2CCC(=CCO)CO)CO)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC=C([C@H]2CC/C(=C/CO)/CO)CO)(C)C
• InChI: InChI=1S/C20H34O3/c1-19(2)10-4-11-20(3)17(7-5-15(13-22)9-12-21)16(14-23)6-8-18(19)20/h6,9,17-18,21-23H,4-5,7-8,10-14H2,1-3H3/b15-9-/t17-,18-,20+/m1/s1
• InChI Key: QKFYQBBBSKOMPQ-ZMYBETPQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.45
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.7283	72.83%
Blood Brain Barrier	+	0.7385	73.85%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.4685	46.85%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8154	81.54%
OATP1B3 inhibitior	+	0.8273	82.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5134	51.34%
BSEP inhibitior	-	0.6055	60.55%
P-glycoprotein inhibitior	-	0.8348	83.48%
P-glycoprotein substrate	-	0.7681	76.81%
CYP3A4 substrate	+	0.5945	59.45%
CYP2C9 substrate	-	0.7664	76.64%
CYP2D6 substrate	-	0.7388	73.88%
CYP3A4 inhibition	-	0.6793	67.93%
CYP2C9 inhibition	-	0.7375	73.75%
CYP2C19 inhibition	-	0.7442	74.42%
CYP2D6 inhibition	-	0.9001	90.01%
CYP1A2 inhibition	-	0.8784	87.84%
CYP2C8 inhibition	-	0.5932	59.32%
CYP inhibitory promiscuity	-	0.5715	57.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6542	65.42%
Eye corrosion	-	0.9772	97.72%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.8171	81.71%
Skin corrosion	-	0.9741	97.41%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3831	38.31%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.6351	63.51%
skin sensitisation	+	0.5702	57.02%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7667	76.67%
Acute Oral Toxicity (c)	IV	0.4927	49.27%
Estrogen receptor binding	+	0.6824	68.24%
Androgen receptor binding	+	0.5320	53.20%
Thyroid receptor binding	+	0.6843	68.43%
Glucocorticoid receptor binding	+	0.7559	75.59%
Aromatase binding	+	0.6188	61.88%
PPAR gamma	+	0.5997	59.97%
Honey bee toxicity	-	0.8458	84.58%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	96.62%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.64%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.81%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.88%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.62%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.24%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.42%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.44%	97.09%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	83.87%	100.00%
CHEMBL2581	P07339	Cathepsin D	83.15%	98.95%

Plants that contains it

• Achyrocline alata

Cross-Links

• PubChem: 38359319
• LOTUS: LTS0206234
• wikiData: Q105223084