8alpha-monoacetoxyphomadecalin D

Details

• Internal ID: 8aa136cc-51b8-41e1-8446-4f1f69522cc6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1aS,2S,6R,7R,7aR,7bR)-6-hydroxy-1a-(3-hydroxyprop-1-en-2-yl)-7,7a-dimethyl-2,6,7,7b-tetrahydronaphtho[1,2-b]oxiren-2-yl] acetate
• SMILES (Canonical): CC1C(C=CC2=CC(C3(C(C12C)O3)C(=C)CO)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H](C=CC2=C[C@@H]([C@]3([C@@H]([C@]12C)O3)C(=C)CO)OC(=O)C)O
• InChI: InChI=1S/C17H22O5/c1-9(8-18)17-14(21-11(3)19)7-12-5-6-13(20)10(2)16(12,4)15(17)22-17/h5-7,10,13-15,18,20H,1,8H2,2-4H3/t10-,13+,14-,15+,16+,17-/m0/s1
• InChI Key: UNYRPNAJDZDQFG-CHXCLDMJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• CHEMBL4540025

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9688	96.88%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6394	63.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8573	85.73%
OATP1B3 inhibitior	+	0.9082	90.82%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8819	88.19%
P-glycoprotein inhibitior	-	0.8332	83.32%
P-glycoprotein substrate	-	0.6342	63.42%
CYP3A4 substrate	+	0.6301	63.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8826	88.26%
CYP3A4 inhibition	-	0.8079	80.79%
CYP2C9 inhibition	-	0.8604	86.04%
CYP2C19 inhibition	-	0.7821	78.21%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.7541	75.41%
CYP2C8 inhibition	-	0.7345	73.45%
CYP inhibitory promiscuity	-	0.6428	64.28%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5925	59.25%
Eye corrosion	-	0.9785	97.85%
Eye irritation	-	0.9697	96.97%
Skin irritation	-	0.6599	65.99%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6599	65.99%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.6265	62.65%
skin sensitisation	-	0.6697	66.97%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7064	70.64%
Acute Oral Toxicity (c)	III	0.4427	44.27%
Estrogen receptor binding	+	0.6782	67.82%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.7002	70.02%
Aromatase binding	+	0.5202	52.02%
PPAR gamma	-	0.5119	51.19%
Honey bee toxicity	-	0.7434	74.34%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7005	70.05%
Fish aquatic toxicity	+	0.9474	94.74%

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	95.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.68%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.50%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.69%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.94%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.49%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	82.94%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.27%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.14%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.97%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.36%	97.28%

Plants that contains it

• Peperomia obtusifolia

Cross-Links

• PubChem: 132556713
• LOTUS: LTS0185034
• wikiData: Q105268946