methyl (2S)-2-[(2S,4aR)-4a,8-dimethyl-3,7-dioxo-2,4-dihydro-1H-naphthalen-2-yl]-2-hydroxypropanoate

Details

• Internal ID: dfccd8bc-e5a9-461a-840a-c71fa0fa0305
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl (2S)-2-[(2S,4aR)-4a,8-dimethyl-3,7-dioxo-2,4-dihydro-1H-naphthalen-2-yl]-2-hydroxypropanoate
• SMILES (Canonical): CC1=C2CC(C(=O)CC2(C=CC1=O)C)C(C)(C(=O)OC)O
• SMILES (Isomeric): CC1=C2C[C@H](C(=O)C[C@@]2(C=CC1=O)C)[C@@](C)(C(=O)OC)O
• InChI: InChI=1S/C16H20O5/c1-9-10-7-11(16(3,20)14(19)21-4)13(18)8-15(10,2)6-5-12(9)17/h5-6,11,20H,7-8H2,1-4H3/t11-,15+,16+/m1/s1
• InChI Key: GSMDJCJCNWPEPQ-RLCCDNCMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.33 g/mol
• Exact Mass: 292.13107373 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.35
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.7301	73.01%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7942	79.42%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8998	89.98%
OATP1B3 inhibitior	+	0.8449	84.49%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7413	74.13%
P-glycoprotein inhibitior	-	0.8857	88.57%
P-glycoprotein substrate	-	0.7592	75.92%
CYP3A4 substrate	+	0.6609	66.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9212	92.12%
CYP3A4 inhibition	-	0.6023	60.23%
CYP2C9 inhibition	-	0.8997	89.97%
CYP2C19 inhibition	-	0.8822	88.22%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.7041	70.41%
CYP2C8 inhibition	-	0.6932	69.32%
CYP inhibitory promiscuity	-	0.9376	93.76%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9563	95.63%
Carcinogenicity (trinary)	Non-required	0.5598	55.98%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.7910	79.10%
Skin irritation	-	0.5445	54.45%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4232	42.32%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5014	50.14%
skin sensitisation	-	0.7757	77.57%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7597	75.97%
Acute Oral Toxicity (c)	III	0.4887	48.87%
Estrogen receptor binding	+	0.5690	56.90%
Androgen receptor binding	-	0.5098	50.98%
Thyroid receptor binding	-	0.5709	57.09%
Glucocorticoid receptor binding	+	0.6079	60.79%
Aromatase binding	-	0.7833	78.33%
PPAR gamma	+	0.5331	53.31%
Honey bee toxicity	-	0.8566	85.66%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9916	99.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.58%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.21%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.49%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.43%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.74%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.55%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.24%	99.23%
CHEMBL220	P22303	Acetylcholinesterase	81.86%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.07%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.25%	99.17%

Plants that contains it

• Salvia palaefolia

Cross-Links

• PubChem: 163037664
• LOTUS: LTS0247533
• wikiData: Q105017347