[(1R,2R,4aS,5R,8aR)-5-hydroxy-1,8a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,4a,5,8-hexahydro-1H-naphthalen-2-yl] (Z,5R)-5-[(Z)-2-methylbut-2-enoyl]oxyhex-2-enoate

Details

• Internal ID: af1eb6ac-bd1d-47d4-a73c-5da6f00c3d18
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1R,2R,4aS,5R,8aR)-5-hydroxy-1,8a-dimethyl-6-oxo-7-propan-2-ylidene-2,3,4,4a,5,8-hexahydro-1H-naphthalen-2-yl] (Z,5R)-5-[(Z)-2-methylbut-2-enoyl]oxyhex-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC(C)CC=CC(=O)OC1CCC2C(C(=O)C(=C(C)C)CC2(C1C)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H](C)C/C=C\C(=O)O[C@@H]1CC[C@@H]2[C@H](C(=O)C(=C(C)C)C[C@@]2([C@H]1C)C)O
• InChI: InChI=1S/C26H38O6/c1-8-16(4)25(30)31-17(5)10-9-11-22(27)32-21-13-12-20-24(29)23(28)19(15(2)3)14-26(20,7)18(21)6/h8-9,11,17-18,20-21,24,29H,10,12-14H2,1-7H3/b11-9-,16-8-/t17-,18+,20-,21-,24-,26-/m1/s1
• InChI Key: ZGTBDTSFLOZSSV-RZHOOMCVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₆
• Molecular Weight: 446.60 g/mol
• Exact Mass: 446.26683893 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.46
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	-	0.6239	62.39%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8852	88.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8671	86.71%
OATP1B3 inhibitior	-	0.4075	40.75%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5564	55.64%
P-glycoprotein inhibitior	+	0.7247	72.47%
P-glycoprotein substrate	-	0.6263	62.63%
CYP3A4 substrate	+	0.6859	68.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9095	90.95%
CYP3A4 inhibition	-	0.7011	70.11%
CYP2C9 inhibition	-	0.8587	85.87%
CYP2C19 inhibition	-	0.8495	84.95%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.8646	86.46%
CYP2C8 inhibition	-	0.7053	70.53%
CYP inhibitory promiscuity	-	0.8821	88.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9637	96.37%
Skin irritation	+	0.5597	55.97%
Skin corrosion	-	0.9708	97.08%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3616	36.16%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.6196	61.96%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5948	59.48%
Acute Oral Toxicity (c)	III	0.6331	63.31%
Estrogen receptor binding	+	0.6990	69.90%
Androgen receptor binding	+	0.5373	53.73%
Thyroid receptor binding	+	0.5282	52.82%
Glucocorticoid receptor binding	+	0.6390	63.90%
Aromatase binding	+	0.5466	54.66%
PPAR gamma	+	0.5935	59.35%
Honey bee toxicity	-	0.7917	79.17%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
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
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.56%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.31%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.12%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	95.73%	90.17%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	95.16%	92.95%
CHEMBL2581	P07339	Cathepsin D	92.75%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.91%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	91.61%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.57%	91.07%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.15%	89.34%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.25%	93.00%
CHEMBL325	Q13547	Histone deacetylase 1	85.49%	95.92%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.45%	97.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.02%	91.24%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.77%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.68%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.56%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.21%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.09%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.02%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.24%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.12%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.60%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.42%	97.25%

Plants that contains it

• Senecio speciosus

Cross-Links

• PubChem: 163038340
• LOTUS: LTS0017130
• wikiData: Q105375426