[(1R,2S,4aR,5R,7R)-7-hydroperoxy-5-hydroxy-4a,8-dimethyl-2-propan-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalen-1-yl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: 960f8f31-2fac-40be-a3e2-7ba36b4455e6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: [(1R,2S,4aR,5R,7R)-7-hydroperoxy-5-hydroxy-4a,8-dimethyl-2-propan-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalen-1-yl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1=C2C(C(CCC2(C(CC1OO)O)C)C(C)C)OC(=O)C=CC3=CC=CC=C3
• SMILES (Isomeric): CC1=C2[C@@H]([C@@H](CC[C@]2([C@@H](C[C@H]1OO)O)C)C(C)C)OC(=O)/C=C/C3=CC=CC=C3
• InChI: InChI=1S/C24H32O5/c1-15(2)18-12-13-24(4)20(25)14-19(29-27)16(3)22(24)23(18)28-21(26)11-10-17-8-6-5-7-9-17/h5-11,15,18-20,23,25,27H,12-14H2,1-4H3/b11-10+/t18-,19+,20+,23+,24-/m0/s1
• InChI Key: RCNVBRCNVUOFOJ-WPXXHNCHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₅
• Molecular Weight: 400.50 g/mol
• Exact Mass: 400.22497412 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	-	0.5729	57.29%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7921	79.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8973	89.73%
OATP1B3 inhibitior	-	0.2251	22.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.8948	89.48%
P-glycoprotein inhibitior	+	0.5988	59.88%
P-glycoprotein substrate	-	0.5810	58.10%
CYP3A4 substrate	+	0.6373	63.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.6800	68.00%
CYP2C9 inhibition	-	0.7179	71.79%
CYP2C19 inhibition	-	0.6953	69.53%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.6146	61.46%
CYP2C8 inhibition	+	0.7260	72.60%
CYP inhibitory promiscuity	-	0.8335	83.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8355	83.55%
Carcinogenicity (trinary)	Non-required	0.5946	59.46%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9636	96.36%
Skin irritation	-	0.5279	52.79%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7053	70.53%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5559	55.59%
skin sensitisation	-	0.7037	70.37%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8551	85.51%
Acute Oral Toxicity (c)	I	0.4391	43.91%
Estrogen receptor binding	+	0.7314	73.14%
Androgen receptor binding	+	0.7085	70.85%
Thyroid receptor binding	+	0.6356	63.56%
Glucocorticoid receptor binding	+	0.6700	67.00%
Aromatase binding	+	0.6273	62.73%
PPAR gamma	+	0.6098	60.98%
Honey bee toxicity	-	0.7389	73.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
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
CHEMBL221	P23219	Cyclooxygenase-1	97.16%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.92%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.91%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.86%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95.06%	94.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.05%	94.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.04%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.65%	96.00%
CHEMBL5028	O14672	ADAM10	90.94%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.21%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.14%	95.50%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	88.04%	97.53%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.81%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.45%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.60%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.28%	96.47%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.79%	93.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.65%	89.44%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.20%	93.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.07%	94.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.84%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.51%	100.00%

Plants that contains it

• Brintonia discoidea

Cross-Links

• PubChem: 163195519
• LOTUS: LTS0036353
• wikiData: Q105233828