(1R)-1-[(2S,4aR,4bR,5S,8aR)-5-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol

Details

• Internal ID: cb1383e5-662a-48ae-9f1f-429e28bb1301
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R)-1-[(2S,4aR,4bR,5S,8aR)-5-hydroxy-2,4b,8,8-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
• SMILES (Canonical): CC1(CCC(C2(C1CCC3=CC(CCC32)(C)C(CO)O)C)O)C
• SMILES (Isomeric): C[C@@]1(CC[C@@H]2C(=C1)CC[C@H]3[C@]2([C@H](CCC3(C)C)O)C)[C@H](CO)O
• InChI: InChI=1S/C20H34O3/c1-18(2)9-8-16(22)20(4)14-7-10-19(3,17(23)12-21)11-13(14)5-6-15(18)20/h11,14-17,21-23H,5-10,12H2,1-4H3/t14-,15-,16+,17+,19+,20+/m1/s1
• InChI Key: QMPZNDBIBKPBLS-SOTAWHFNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.5951	59.51%
Blood Brain Barrier	+	0.6885	68.85%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7818	78.18%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.9187	91.87%
OATP1B3 inhibitior	+	0.9525	95.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6083	60.83%
BSEP inhibitior	-	0.4844	48.44%
P-glycoprotein inhibitior	-	0.8582	85.82%
P-glycoprotein substrate	-	0.6616	66.16%
CYP3A4 substrate	+	0.5756	57.56%
CYP2C9 substrate	-	0.6197	61.97%
CYP2D6 substrate	-	0.7438	74.38%
CYP3A4 inhibition	-	0.7785	77.85%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8556	85.56%
CYP2D6 inhibition	-	0.9316	93.16%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	-	0.8079	80.79%
CYP inhibitory promiscuity	-	0.8579	85.79%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7041	70.41%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9632	96.32%
Skin irritation	-	0.6197	61.97%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6571	65.71%
skin sensitisation	-	0.7317	73.17%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8865	88.65%
Acute Oral Toxicity (c)	III	0.6985	69.85%
Estrogen receptor binding	+	0.6904	69.04%
Androgen receptor binding	+	0.6323	63.23%
Thyroid receptor binding	+	0.7480	74.80%
Glucocorticoid receptor binding	+	0.8520	85.20%
Aromatase binding	+	0.6386	63.86%
PPAR gamma	-	0.5214	52.14%
Honey bee toxicity	-	0.8960	89.60%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9725	97.25%

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	96.04%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.56%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.65%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.89%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.40%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.59%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.76%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.48%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.01%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.73%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.13%	82.69%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.29%	100.00%

Plants that contains it

• Bruguiera gymnorhiza

Cross-Links

• PubChem: 163059497
• LOTUS: LTS0016374
• wikiData: Q105224113