[(1R,2R,4aS,5R,7R,8aR)-1,8a-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-6-oxo-7-prop-1-en-2-yl-1,2,3,4,4a,5,7,8-octahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 0e783bd8-a805-40e5-9d6b-8e573e091365
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1R,2R,4aS,5R,7R,8aR)-1,8a-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-6-oxo-7-prop-1-en-2-yl-1,2,3,4,4a,5,7,8-octahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCC2C(C(=O)C(CC2(C1C)C)C(=C)C)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1CC[C@@H]2[C@H](C(=O)[C@H](C[C@@]2([C@H]1C)C)C(=C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C25H36O5/c1-9-15(5)23(27)29-20-12-11-19-22(30-24(28)16(6)10-2)21(26)18(14(3)4)13-25(19,8)17(20)7/h9-10,17-20,22H,3,11-13H2,1-2,4-8H3/b15-9-,16-10-/t17-,18+,19+,20+,22+,25+/m0/s1
• InChI Key: QTZULONSECXBEU-CJAVWFLOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.50 g/mol
• Exact Mass: 416.25627424 g/mol
• Topological Polar Surface Area (TPSA): 69.70 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 4.96
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.5713	57.13%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7767	77.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8821	88.21%
OATP1B3 inhibitior	+	0.9118	91.18%
MATE1 inhibitior	+	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7439	74.39%
P-glycoprotein inhibitior	+	0.7466	74.66%
P-glycoprotein substrate	-	0.7092	70.92%
CYP3A4 substrate	+	0.6778	67.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9075	90.75%
CYP3A4 inhibition	-	0.5746	57.46%
CYP2C9 inhibition	-	0.9222	92.22%
CYP2C19 inhibition	-	0.8517	85.17%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.8452	84.52%
CYP2C8 inhibition	-	0.7609	76.09%
CYP inhibitory promiscuity	-	0.9265	92.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5977	59.77%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9098	90.98%
Skin irritation	+	0.5524	55.24%
Skin corrosion	-	0.9695	96.95%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6438	64.38%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6461	64.61%
skin sensitisation	-	0.6272	62.72%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.8370	83.70%
Acute Oral Toxicity (c)	III	0.6529	65.29%
Estrogen receptor binding	+	0.7980	79.80%
Androgen receptor binding	+	0.5408	54.08%
Thyroid receptor binding	+	0.6121	61.21%
Glucocorticoid receptor binding	+	0.7924	79.24%
Aromatase binding	+	0.6278	62.78%
PPAR gamma	+	0.6348	63.48%
Honey bee toxicity	-	0.5742	57.42%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.02%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.44%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	89.43%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.23%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.94%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.23%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.98%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.49%	93.04%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.33%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.00%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.87%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.63%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.61%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.30%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.19%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.07%	94.45%

Plants that contains it

• Senecio provincialis

Cross-Links

• PubChem: 162906343
• LOTUS: LTS0113819
• wikiData: Q105228012