methyl 2-[(2R,3R,4aR,8aR)-3-acetyloxy-4a-methyl-8-methylidene-7-oxo-2,3,4,8a-tetrahydro-1H-naphthalen-2-yl]prop-2-enoate

Details

• Internal ID: 26202b94-5667-41b1-8782-b7bc63d50d45
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: methyl 2-[(2R,3R,4aR,8aR)-3-acetyloxy-4a-methyl-8-methylidene-7-oxo-2,3,4,8a-tetrahydro-1H-naphthalen-2-yl]prop-2-enoate
• SMILES (Canonical): CC(=O)OC1CC2(C=CC(=O)C(=C)C2CC1C(=C)C(=O)OC)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@]2(C=CC(=O)C(=C)[C@@H]2C[C@@H]1C(=C)C(=O)OC)C
• InChI: InChI=1S/C18H22O5/c1-10(17(21)22-5)13-8-14-11(2)15(20)6-7-18(14,4)9-16(13)23-12(3)19/h6-7,13-14,16H,1-2,8-9H2,3-5H3/t13-,14+,16-,18+/m1/s1
• InChI Key: GJAARPKBDFKHFS-KKBFJZEXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.14672380 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.5344	53.44%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7229	72.29%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9238	92.38%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7434	74.34%
P-glycoprotein inhibitior	-	0.5100	51.00%
P-glycoprotein substrate	-	0.6374	63.74%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9038	90.38%
CYP3A4 inhibition	+	0.7518	75.18%
CYP2C9 inhibition	-	0.8928	89.28%
CYP2C19 inhibition	-	0.8682	86.82%
CYP2D6 inhibition	-	0.9552	95.52%
CYP1A2 inhibition	-	0.8249	82.49%
CYP2C8 inhibition	-	0.8104	81.04%
CYP inhibitory promiscuity	-	0.8588	85.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8176	81.76%
Carcinogenicity (trinary)	Non-required	0.5736	57.36%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.8835	88.35%
Skin irritation	-	0.6394	63.94%
Skin corrosion	-	0.9792	97.92%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7472	74.72%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5928	59.28%
skin sensitisation	-	0.5823	58.23%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7408	74.08%
Acute Oral Toxicity (c)	III	0.7023	70.23%
Estrogen receptor binding	+	0.7149	71.49%
Androgen receptor binding	+	0.5904	59.04%
Thyroid receptor binding	-	0.5274	52.74%
Glucocorticoid receptor binding	+	0.5575	55.75%
Aromatase binding	-	0.7007	70.07%
PPAR gamma	+	0.5347	53.47%
Honey bee toxicity	-	0.6925	69.25%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.83%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.82%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.09%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.02%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.88%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.57%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	82.70%	90.17%
CHEMBL4208	P20618	Proteasome component C5	80.47%	90.00%

Plants that contains it

• Geraea viscida

Cross-Links

• PubChem: 162878597
• LOTUS: LTS0143603
• wikiData: Q105009303