[(1S,2R,4aR,5R,8R,8aS)-5,8-dihydroxy-4a,8-dimethyl-2-propan-2-yl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 3f8a0980-287a-46b3-bccc-821539c107ef
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(1S,2R,4aR,5R,8R,8aS)-5,8-dihydroxy-4a,8-dimethyl-2-propan-2-yl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(C)C1CCC2(C(CCC(C2C1OC(=O)C=CC3=CC=C(C=C3)O)(C)O)O)C
• SMILES (Isomeric): CC(C)[C@H]1CC[C@]2([C@@H](CC[C@@]([C@@H]2[C@H]1OC(=O)/C=C/C3=CC=C(C=C3)O)(C)O)O)C
• InChI: InChI=1S/C24H34O5/c1-15(2)18-11-13-23(3)19(26)12-14-24(4,28)22(23)21(18)29-20(27)10-7-16-5-8-17(25)9-6-16/h5-10,15,18-19,21-22,25-26,28H,11-14H2,1-4H3/b10-7+/t18-,19-,21+,22-,23+,24-/m1/s1
• InChI Key: MJYKKLXXDFOCHW-UYQLHEEMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₅
• Molecular Weight: 402.50 g/mol
• Exact Mass: 402.24062418 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

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	-	0.5929	59.29%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8353	83.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9023	90.23%
OATP1B3 inhibitior	+	0.8029	80.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8821	88.21%
BSEP inhibitior	+	0.6461	64.61%
P-glycoprotein inhibitior	-	0.6700	67.00%
P-glycoprotein substrate	-	0.6371	63.71%
CYP3A4 substrate	+	0.6811	68.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.6487	64.87%
CYP2C9 inhibition	-	0.7637	76.37%
CYP2C19 inhibition	-	0.6346	63.46%
CYP2D6 inhibition	-	0.9616	96.16%
CYP1A2 inhibition	+	0.6244	62.44%
CYP2C8 inhibition	+	0.5273	52.73%
CYP inhibitory promiscuity	-	0.9087	90.87%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8955	89.55%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9947	99.47%
Eye irritation	-	0.9624	96.24%
Skin irritation	-	0.5147	51.47%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.7970	79.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6600	66.00%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5685	56.85%
skin sensitisation	-	0.7660	76.60%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.9176	91.76%
Acute Oral Toxicity (c)	I	0.5361	53.61%
Estrogen receptor binding	+	0.8512	85.12%
Androgen receptor binding	+	0.7188	71.88%
Thyroid receptor binding	+	0.7429	74.29%
Glucocorticoid receptor binding	+	0.7336	73.36%
Aromatase binding	+	0.7006	70.06%
PPAR gamma	+	0.5833	58.33%
Honey bee toxicity	-	0.8355	83.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
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	97.16%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	95.81%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.49%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.80%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.67%	97.09%
CHEMBL206	P03372	Estrogen receptor alpha	92.03%	97.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.72%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.67%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.36%	94.45%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.68%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.60%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.88%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	85.85%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.76%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.37%	94.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.15%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.19%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.35%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.13%	95.93%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.08%	89.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.23%	93.56%

Plants that contains it

• Verbesina virginica

Cross-Links

• PubChem: 163195204
• LOTUS: LTS0275027
• wikiData: Q105165745