(2S,4aS,4bR,7R,8aR)-2-ethenyl-7-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,7,8a,9-hexahydro-1H-phenanthrene-3,6-dione

Details

• Internal ID: ef55159a-c365-4d6f-8f41-42c33b59086e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2S,4aS,4bR,7R,8aR)-2-ethenyl-7-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,7,8a,9-hexahydro-1H-phenanthrene-3,6-dione
• SMILES (Canonical): CC1(C2CC=C3CC(C(=O)CC3C2(CC(=O)C1O)C)(C)C=C)C
• SMILES (Isomeric): C[C@]1(CC2=CC[C@@H]3[C@@]([C@H]2CC1=O)(CC(=O)[C@@H](C3(C)C)O)C)C=C
• InChI: InChI=1S/C20H28O3/c1-6-19(4)10-12-7-8-15-18(2,3)17(23)14(21)11-20(15,5)13(12)9-16(19)22/h6-7,13,15,17,23H,1,8-11H2,2-5H3/t13-,15-,17-,19+,20+/m0/s1
• InChI Key: ZTJAMBHQVLABGR-HKIZTLLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• 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	+	0.5125	51.25%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8642	86.42%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8991	89.91%
OATP1B3 inhibitior	+	0.8755	87.55%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.5984	59.84%
P-glycoprotein inhibitior	-	0.8692	86.92%
P-glycoprotein substrate	-	0.8590	85.90%
CYP3A4 substrate	+	0.6057	60.57%
CYP2C9 substrate	-	0.8495	84.95%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	-	0.5336	53.36%
CYP2C9 inhibition	-	0.8415	84.15%
CYP2C19 inhibition	-	0.7162	71.62%
CYP2D6 inhibition	-	0.9372	93.72%
CYP1A2 inhibition	-	0.9067	90.67%
CYP2C8 inhibition	-	0.8053	80.53%
CYP inhibitory promiscuity	-	0.8827	88.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5912	59.12%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.5189	51.89%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.5728	57.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7011	70.11%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5959	59.59%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.8094	80.94%
Acute Oral Toxicity (c)	III	0.6593	65.93%
Estrogen receptor binding	+	0.5885	58.85%
Androgen receptor binding	+	0.5615	56.15%
Thyroid receptor binding	+	0.6095	60.95%
Glucocorticoid receptor binding	+	0.7803	78.03%
Aromatase binding	-	0.4926	49.26%
PPAR gamma	+	0.5368	53.68%
Honey bee toxicity	-	0.7649	76.49%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.06%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.06%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.83%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.05%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.52%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.59%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.40%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.43%	100.00%

Plants that contains it

• Euphorbia jolkinii

Cross-Links

• PubChem: 25156380
• LOTUS: LTS0189731
• wikiData: Q105382946