(E)-5-[(1S,2R,4aR,8aR)-2-(hydroxymethyl)-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-ol

Details

• Internal ID: 8655884f-1cda-4a0d-9f8e-a07b053709a5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (E)-5-[(1S,2R,4aR,8aR)-2-(hydroxymethyl)-1,4a,5-trimethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylpent-2-en-1-ol
• SMILES (Canonical): CC1=CCCC2C1(CCC(C2(C)CCC(=CCO)C)CO)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1(CC[C@H]([C@@]2(C)CC/C(=C/CO)/C)CO)C
• InChI: InChI=1S/C20H34O2/c1-15(10-13-21)8-11-20(4)17(14-22)9-12-19(3)16(2)6-5-7-18(19)20/h6,10,17-18,21-22H,5,7-9,11-14H2,1-4H3/b15-10+/t17-,18-,19-,20+/m0/s1
• InChI Key: SBPZKXANBXYCRD-CHDXTAOESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.50 g/mol
• Exact Mass: 306.255880323 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	+	0.8146	81.46%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.6167	61.67%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.8373	83.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5593	55.93%
BSEP inhibitior	-	0.5980	59.80%
P-glycoprotein inhibitior	-	0.8500	85.00%
P-glycoprotein substrate	-	0.8496	84.96%
CYP3A4 substrate	+	0.5691	56.91%
CYP2C9 substrate	-	0.7664	76.64%
CYP2D6 substrate	-	0.7388	73.88%
CYP3A4 inhibition	-	0.6389	63.89%
CYP2C9 inhibition	-	0.6936	69.36%
CYP2C19 inhibition	-	0.6560	65.60%
CYP2D6 inhibition	-	0.8900	89.00%
CYP1A2 inhibition	-	0.8033	80.33%
CYP2C8 inhibition	-	0.6356	63.56%
CYP inhibitory promiscuity	-	0.5741	57.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6160	61.60%
Eye corrosion	-	0.9675	96.75%
Eye irritation	-	0.9195	91.95%
Skin irritation	-	0.8224	82.24%
Skin corrosion	-	0.9763	97.63%
Ames mutagenesis	-	0.6566	65.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.7892	78.92%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6351	63.51%
skin sensitisation	+	0.4767	47.67%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5765	57.65%
Acute Oral Toxicity (c)	III	0.5348	53.48%
Estrogen receptor binding	+	0.6963	69.63%
Androgen receptor binding	-	0.4813	48.13%
Thyroid receptor binding	+	0.6840	68.40%
Glucocorticoid receptor binding	+	0.5694	56.94%
Aromatase binding	+	0.6459	64.59%
PPAR gamma	+	0.6652	66.52%
Honey bee toxicity	-	0.9113	91.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9908	99.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.68%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.41%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.08%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.62%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.76%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.64%	94.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.37%	95.50%

Plants that contains it

• Symphyopappus reticulatus

Cross-Links

• PubChem: 163042252
• LOTUS: LTS0238856
• wikiData: Q105249604