methyl 2-[(1S,2S,4aR,5S,8aS)-1,5-dihydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoate

Details

• Internal ID: fdfa21c6-099f-47e8-accb-7735bff8400d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-[(1S,2S,4aR,5S,8aS)-1,5-dihydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC1=CCC(C2(C1C(C(CC2)C(=C)C(=O)OC)O)C)O
• SMILES (Isomeric): CC1=CC[C@@H]([C@]2([C@H]1[C@H]([C@@H](CC2)C(=C)C(=O)OC)O)C)O
• InChI: InChI=1S/C16H24O4/c1-9-5-6-12(17)16(3)8-7-11(14(18)13(9)16)10(2)15(19)20-4/h5,11-14,17-18H,2,6-8H2,1,3-4H3/t11-,12-,13+,14-,16-/m0/s1
• InChI Key: AXEGVGVJBISYSU-HAFSJTIUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.36 g/mol
• Exact Mass: 280.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	+	0.6041	60.41%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9364	93.64%
OATP1B3 inhibitior	-	0.3943	39.43%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.8301	83.01%
P-glycoprotein inhibitior	-	0.8711	87.11%
P-glycoprotein substrate	-	0.8442	84.42%
CYP3A4 substrate	+	0.6778	67.78%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8432	84.32%
CYP3A4 inhibition	-	0.6806	68.06%
CYP2C9 inhibition	-	0.8265	82.65%
CYP2C19 inhibition	-	0.8728	87.28%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.7534	75.34%
CYP2C8 inhibition	-	0.6963	69.63%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6696	66.96%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9109	91.09%
Skin irritation	+	0.5650	56.50%
Skin corrosion	-	0.9630	96.30%
Ames mutagenesis	-	0.7523	75.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6472	64.72%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6719	67.19%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6810	68.10%
Acute Oral Toxicity (c)	III	0.6488	64.88%
Estrogen receptor binding	+	0.6234	62.34%
Androgen receptor binding	+	0.5974	59.74%
Thyroid receptor binding	+	0.5433	54.33%
Glucocorticoid receptor binding	+	0.6481	64.81%
Aromatase binding	-	0.7189	71.89%
PPAR gamma	-	0.5192	51.92%
Honey bee toxicity	-	0.8289	82.89%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9951	99.51%

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	96.87%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	96.49%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.27%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.57%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.77%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.67%	98.95%
CHEMBL1871	P10275	Androgen Receptor	85.10%	96.43%
CHEMBL5028	O14672	ADAM10	83.10%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.47%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.79%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.30%	89.00%

Plants that contains it

• Tanacetum praeteritum

Cross-Links

• PubChem: 10356321
• LOTUS: LTS0144920
• wikiData: Q104920489