(2R,4aR,4bR,5S,7R,8aR)-7-ethenyl-1,1,4b,7-tetramethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthrene-2,5-diol

Details

• Internal ID: 1e2362f8-5c72-45af-b136-f6b58a25af68
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R,4aR,4bR,5S,7R,8aR)-7-ethenyl-1,1,4b,7-tetramethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthrene-2,5-diol
• SMILES (Canonical): CC1(C(CCC2C1=CCC3C2(C(CC(C3)(C)C=C)O)C)O)C
• SMILES (Isomeric): C[C@]1(C[C@H]2CC=C3[C@H]([C@@]2([C@H](C1)O)C)CC[C@H](C3(C)C)O)C=C
• InChI: InChI=1S/C20H32O2/c1-6-19(4)11-13-7-8-14-15(20(13,5)17(22)12-19)9-10-16(21)18(14,2)3/h6,8,13,15-17,21-22H,1,7,9-12H2,2-5H3/t13-,15-,16-,17+,19-,20-/m1/s1
• InChI Key: HTASYHXPILTPQF-VIDQEAKSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.50 g/mol
• Exact Mass: 304.240230259 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.08
• H-Bond Acceptor: 2
• 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	+	0.9971	99.71%
Caco-2	+	0.7222	72.22%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5322	53.22%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7925	79.25%
P-glycoprotein inhibitior	-	0.8762	87.62%
P-glycoprotein substrate	-	0.7371	73.71%
CYP3A4 substrate	+	0.5952	59.52%
CYP2C9 substrate	-	0.6499	64.99%
CYP2D6 substrate	-	0.6843	68.43%
CYP3A4 inhibition	-	0.8622	86.22%
CYP2C9 inhibition	-	0.8744	87.44%
CYP2C19 inhibition	-	0.6994	69.94%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.8204	82.04%
CYP2C8 inhibition	-	0.7611	76.11%
CYP inhibitory promiscuity	-	0.7234	72.34%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5982	59.82%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8987	89.87%
Skin irritation	+	0.5123	51.23%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	-	0.7708	77.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.8265	82.65%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	+	0.6144	61.44%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6494	64.94%
Acute Oral Toxicity (c)	III	0.8445	84.45%
Estrogen receptor binding	+	0.7798	77.98%
Androgen receptor binding	-	0.5682	56.82%
Thyroid receptor binding	+	0.7511	75.11%
Glucocorticoid receptor binding	+	0.6206	62.06%
Aromatase binding	-	0.5053	50.53%
PPAR gamma	-	0.5309	53.09%
Honey bee toxicity	-	0.8896	88.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9824	98.24%

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	95.40%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.90%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.87%	90.17%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.23%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.14%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.61%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.48%	97.09%
CHEMBL1871	P10275	Androgen Receptor	83.12%	96.43%
CHEMBL226	P30542	Adenosine A1 receptor	81.62%	95.93%

Plants that contains it

• Premna serratifolia

Cross-Links

• PubChem: 56970841
• LOTUS: LTS0151417
• wikiData: Q105033344