(2S,4bS,7R,8aR,10aR)-7-ethenyl-4b-(hydroxymethyl)-1,1,7-trimethyl-3,5,6,8,8a,9,10,10a-octahydro-2H-phenanthren-2-ol

Details

• Internal ID: b2c85f7c-0ae5-4a4a-9793-74ad6b9bd09e
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: (2S,4bS,7R,8aR,10aR)-7-ethenyl-4b-(hydroxymethyl)-1,1,7-trimethyl-3,5,6,8,8a,9,10,10a-octahydro-2H-phenanthren-2-ol
• SMILES (Canonical): CC1(C2CCC3CC(CCC3(C2=CCC1O)CO)(C)C=C)C
• SMILES (Isomeric): C[C@]1(CC[C@@]2([C@@H](C1)CC[C@@H]3C2=CC[C@@H](C3(C)C)O)CO)C=C
• InChI: InChI=1S/C20H32O2/c1-5-19(4)10-11-20(13-21)14(12-19)6-7-15-16(20)8-9-17(22)18(15,2)3/h5,8,14-15,17,21-22H,1,6-7,9-13H2,2-4H3/t14-,15-,17+,19-,20+/m1/s1
• InChI Key: XHDDXJBGGUJQQL-XUMMFJMYSA-N
• Popularity: 1 reference 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: 4.40
• Atomic LogP (AlogP): 4.08
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.7312	73.12%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5813	58.13%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8853	88.53%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5885	58.85%
BSEP inhibitior	-	0.6099	60.99%
P-glycoprotein inhibitior	-	0.8853	88.53%
P-glycoprotein substrate	-	0.7946	79.46%
CYP3A4 substrate	+	0.6146	61.46%
CYP2C9 substrate	-	0.6284	62.84%
CYP2D6 substrate	-	0.7222	72.22%
CYP3A4 inhibition	-	0.7840	78.40%
CYP2C9 inhibition	-	0.8828	88.28%
CYP2C19 inhibition	-	0.8176	81.76%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	-	0.8714	87.14%
CYP2C8 inhibition	-	0.6102	61.02%
CYP inhibitory promiscuity	-	0.7100	71.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6763	67.63%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8967	89.67%
Skin irritation	-	0.6518	65.18%
Skin corrosion	-	0.9611	96.11%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6940	69.40%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.6236	62.36%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8058	80.58%
Acute Oral Toxicity (c)	III	0.8312	83.12%
Estrogen receptor binding	+	0.8420	84.20%
Androgen receptor binding	-	0.4820	48.20%
Thyroid receptor binding	+	0.6646	66.46%
Glucocorticoid receptor binding	+	0.8097	80.97%
Aromatase binding	+	0.5745	57.45%
PPAR gamma	-	0.5860	58.60%
Honey bee toxicity	-	0.8162	81.62%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.35%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.78%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.08%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.48%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.11%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.31%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.18%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.08%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.03%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.93%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.37%	90.24%

Plants that contains it

• Euphorbia ebracteolata

Cross-Links

• PubChem: 90670339
• NPASS: NPC471799
• ChEMBL: CHEMBL3234216
• LOTUS: LTS0047230
• wikiData: Q105328025