methyl 2-[1,5-dihydroxy-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoate

Details

• Internal ID: bdf2c99e-f18c-4cac-a155-9197ee615e45
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-[1,5-dihydroxy-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC12CCC(C(C1C(CCC2O)CO)O)C(=C)C(=O)OC
• SMILES (Isomeric): CC12CCC(C(C1C(CCC2O)CO)O)C(=C)C(=O)OC
• InChI: InChI=1S/C16H26O5/c1-9(15(20)21-3)11-6-7-16(2)12(18)5-4-10(8-17)13(16)14(11)19/h10-14,17-19H,1,4-8H2,2-3H3
• InChI Key: HRYRCTBIBAAZJJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₅
• Molecular Weight: 298.37 g/mol
• Exact Mass: 298.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.5861	58.61%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8426	84.26%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9252	92.52%
OATP1B3 inhibitior	+	0.8511	85.11%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6303	63.03%
BSEP inhibitior	-	0.7475	74.75%
P-glycoprotein inhibitior	-	0.9014	90.14%
P-glycoprotein substrate	-	0.6590	65.90%
CYP3A4 substrate	+	0.6556	65.56%
CYP2C9 substrate	-	0.8199	81.99%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.6242	62.42%
CYP2C9 inhibition	-	0.8449	84.49%
CYP2C19 inhibition	-	0.8769	87.69%
CYP2D6 inhibition	-	0.9218	92.18%
CYP1A2 inhibition	-	0.8069	80.69%
CYP2C8 inhibition	-	0.8447	84.47%
CYP inhibitory promiscuity	-	0.8664	86.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7230	72.30%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.6173	61.73%
Skin corrosion	-	0.9687	96.87%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6050	60.50%
skin sensitisation	-	0.8295	82.95%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5736	57.36%
Acute Oral Toxicity (c)	III	0.6913	69.13%
Estrogen receptor binding	+	0.7220	72.20%
Androgen receptor binding	+	0.6438	64.38%
Thyroid receptor binding	-	0.5238	52.38%
Glucocorticoid receptor binding	+	0.8142	81.42%
Aromatase binding	-	0.6061	60.61%
PPAR gamma	-	0.5725	57.25%
Honey bee toxicity	-	0.8769	87.69%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.47%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.89%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.97%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.75%	96.38%
CHEMBL2581	P07339	Cathepsin D	89.86%	98.95%
CHEMBL204	P00734	Thrombin	89.47%	96.01%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.92%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.10%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.36%	97.09%
CHEMBL5028	O14672	ADAM10	85.31%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.99%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.67%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.27%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.16%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.11%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.64%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	83.43%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.14%	95.89%
CHEMBL1075317	P61964	WD repeat-containing protein 5	83.14%	96.33%
CHEMBL226	P30542	Adenosine A1 receptor	82.64%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.27%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	82.04%	91.19%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.79%	95.83%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.60%	95.50%

Plants that contains it

• Sonchus macrocarpus

Cross-Links

• PubChem: 163025778
• LOTUS: LTS0153773
• wikiData: Q105032904