[(2R,4aR,4bR,8aS,9R,10S)-2,10-dihydroxy-4b,8,8-trimethyl-2-propan-2-yl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-9-yl] 3-methylbut-2-enoate

Details

• Internal ID: e66f63fc-e26f-4bfb-8718-3f92ba2ed699
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4aR,4bR,8aS,9R,10S)-2,10-dihydroxy-4b,8,8-trimethyl-2-propan-2-yl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-9-yl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(C)C1(CCC2C(=C1)C(C(C3C2(CCCC3(C)C)C)OC(=O)C=C(C)C)O)O
• SMILES (Isomeric): CC(C)[C@@]1(CC[C@H]2C(=C1)[C@@H]([C@@H]([C@@H]3[C@@]2(CCCC3(C)C)C)OC(=O)C=C(C)C)O)O
• InChI: InChI=1S/C25H40O4/c1-15(2)13-19(26)29-21-20(27)17-14-25(28,16(3)4)12-9-18(17)24(7)11-8-10-23(5,6)22(21)24/h13-14,16,18,20-22,27-28H,8-12H2,1-7H3/t18-,20-,21-,22-,24+,25-/m0/s1
• InChI Key: KEENXIBOPJRZDN-ZHMAKZFUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₀O₄
• Molecular Weight: 404.60 g/mol
• Exact Mass: 404.29265975 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.6881	68.81%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8741	87.41%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	-	0.2352	23.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6071	60.71%
BSEP inhibitior	+	0.6828	68.28%
P-glycoprotein inhibitior	-	0.6011	60.11%
P-glycoprotein substrate	-	0.7161	71.61%
CYP3A4 substrate	+	0.6457	64.57%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.8488	84.88%
CYP2C9 inhibition	-	0.8429	84.29%
CYP2C19 inhibition	-	0.8624	86.24%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.8151	81.51%
CYP2C8 inhibition	-	0.7230	72.30%
CYP inhibitory promiscuity	-	0.9219	92.19%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6672	66.72%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.9614	96.14%
Skin irritation	+	0.6168	61.68%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4239	42.39%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.6174	61.74%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5167	51.67%
Acute Oral Toxicity (c)	III	0.6001	60.01%
Estrogen receptor binding	+	0.7460	74.60%
Androgen receptor binding	+	0.6282	62.82%
Thyroid receptor binding	+	0.5848	58.48%
Glucocorticoid receptor binding	+	0.7887	78.87%
Aromatase binding	+	0.5768	57.68%
PPAR gamma	+	0.6335	63.35%
Honey bee toxicity	-	0.7374	73.74%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5148	51.48%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.96%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.61%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.62%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.41%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.50%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.09%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.02%	93.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.81%	93.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.66%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.17%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.96%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.76%	89.00%
CHEMBL5028	O14672	ADAM10	82.60%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	82.40%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.94%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.66%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.29%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	80.26%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.19%	86.33%

Plants that contains it

• Solidago juncea

Cross-Links

• PubChem: 162847687
• LOTUS: LTS0069065
• wikiData: Q105139910