[(1S,2R,4aR,8aR)-1-acetyloxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 9edf3edd-a7c6-4f46-b35f-34f314968a32
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2R,4aR,8aR)-1-acetyloxy-1,4a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2CCC3(CC(=O)C(=C(C)C)CC3C2(C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1[C@@](O1)(C)C(=O)O[C@@H]2CC[C@@]3(CC(=O)C(=C(C)C)C[C@H]3[C@]2(C)OC(=O)C)C
• InChI: InChI=1S/C22H32O6/c1-12(2)15-10-17-20(5,11-16(15)24)9-8-18(22(17,7)28-14(4)23)26-19(25)21(6)13(3)27-21/h13,17-18H,8-11H2,1-7H3/t13-,17-,18-,20-,21+,22+/m1/s1
• InChI Key: APZBLWQCTHVAMR-AWJYEWCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₆
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.21988874 g/mol
• Topological Polar Surface Area (TPSA): 82.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 6
• 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	+	0.9876	98.76%
Caco-2	+	0.7024	70.24%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7271	72.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9204	92.04%
MATE1 inhibitior	+	0.5200	52.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7424	74.24%
P-glycoprotein inhibitior	+	0.6099	60.99%
P-glycoprotein substrate	-	0.7692	76.92%
CYP3A4 substrate	+	0.6593	65.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9003	90.03%
CYP3A4 inhibition	-	0.7608	76.08%
CYP2C9 inhibition	-	0.8075	80.75%
CYP2C19 inhibition	-	0.7490	74.90%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.6093	60.93%
CYP2C8 inhibition	-	0.7044	70.44%
CYP inhibitory promiscuity	-	0.9021	90.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.6192	61.92%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8314	83.14%
Skin irritation	-	0.5549	55.49%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4413	44.13%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5429	54.29%
skin sensitisation	-	0.6438	64.38%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5239	52.39%
Acute Oral Toxicity (c)	III	0.5462	54.62%
Estrogen receptor binding	+	0.7924	79.24%
Androgen receptor binding	+	0.6147	61.47%
Thyroid receptor binding	+	0.6424	64.24%
Glucocorticoid receptor binding	+	0.6316	63.16%
Aromatase binding	+	0.5471	54.71%
PPAR gamma	+	0.7158	71.58%
Honey bee toxicity	-	0.8053	80.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5850	58.50%
Fish aquatic toxicity	+	0.9953	99.53%

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	99.01%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.41%	97.25%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	93.59%	85.30%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.77%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	90.43%	98.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.08%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	89.43%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.36%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.49%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.20%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.28%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.76%	97.14%
CHEMBL2996	Q05655	Protein kinase C delta	83.31%	97.79%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.29%	80.96%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.71%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.62%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.62%	97.09%

Plants that contains it

• Epaltes mexicana
• Neurolaena lobata

Cross-Links

• PubChem: 38358005
• LOTUS: LTS0085902
• wikiData: Q104916641