(2R,4aR,4bR,5S,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-2,5-diol

Details

• Internal ID: a0b336e1-a970-43eb-9aa8-a2775314b4d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2R,4aR,4bR,5S,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-2,5-diol
• SMILES (Canonical): CC1(C2CCC3=CC(CC(C3C2(CCC1O)C)O)(C)C=C)C
• SMILES (Isomeric): C[C@@]12CC[C@H](C([C@H]1CCC3=C[C@@](C[C@@H]([C@@H]23)O)(C)C=C)(C)C)O
• InChI: InChI=1S/C20H32O2/c1-6-19(4)11-13-7-8-15-18(2,3)16(22)9-10-20(15,5)17(13)14(21)12-19/h6,11,14-17,21-22H,1,7-10,12H2,2-5H3/t14-,15+,16+,17-,19+,20+/m0/s1
• InChI Key: NOMCEPDYZFZNLH-KUIXFMFUSA-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: 4.20
• 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	+	0.9970	99.70%
Caco-2	+	0.7087	70.87%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5963	59.63%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.9303	93.03%
OATP1B3 inhibitior	+	0.9350	93.50%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.5583	55.83%
P-glycoprotein inhibitior	-	0.8805	88.05%
P-glycoprotein substrate	-	0.8765	87.65%
CYP3A4 substrate	+	0.6332	63.32%
CYP2C9 substrate	-	0.6499	64.99%
CYP2D6 substrate	-	0.6843	68.43%
CYP3A4 inhibition	-	0.8250	82.50%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.6840	68.40%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.8333	83.33%
CYP2C8 inhibition	-	0.7509	75.09%
CYP inhibitory promiscuity	-	0.7618	76.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6019	60.19%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9597	95.97%
Skin irritation	+	0.5084	50.84%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.7223	72.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6943	69.43%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.5415	54.15%
skin sensitisation	+	0.5756	57.56%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8073	80.73%
Acute Oral Toxicity (c)	III	0.8413	84.13%
Estrogen receptor binding	+	0.6869	68.69%
Androgen receptor binding	+	0.5796	57.96%
Thyroid receptor binding	+	0.6462	64.62%
Glucocorticoid receptor binding	+	0.6819	68.19%
Aromatase binding	+	0.5673	56.73%
PPAR gamma	-	0.5661	56.61%
Honey bee toxicity	-	0.8317	83.17%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9928	99.28%

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	94.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.79%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.11%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.56%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.42%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	83.25%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.67%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	82.27%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.08%	82.69%
CHEMBL240	Q12809	HERG	81.39%	89.76%
CHEMBL221	P23219	Cyclooxygenase-1	80.04%	90.17%

Plants that contains it

• Erythroxylum cuneatum

Cross-Links

• PubChem: 162920052
• LOTUS: LTS0218148
• wikiData: Q105182638