[(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-prop-1-en-2-yl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] (Z,4R)-4-[(Z)-2-methylbut-2-enoyl]oxyhex-2-enoate

Details

• Internal ID: cfe6ba76-8d28-4022-855b-a7f8a3f2e4a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1R,2R,4aR,5S,6R,7S,8aR)-5,6-dihydroxy-1,8a-dimethyl-7-prop-1-en-2-yl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl] (Z,4R)-4-[(Z)-2-methylbut-2-enoyl]oxyhex-2-enoate
• SMILES (Canonical): CCC(C=CC(=O)OC1CCC2C(C(C(CC2(C1C)C)C(=C)C)O)O)OC(=O)C(=CC)C
• SMILES (Isomeric): CC[C@H](/C=C\C(=O)O[C@@H]1CC[C@H]2[C@@H]([C@@H]([C@@H](C[C@@]2([C@H]1C)C)C(=C)C)O)O)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C26H40O6/c1-8-16(5)25(30)31-18(9-2)10-13-22(27)32-21-12-11-20-24(29)23(28)19(15(3)4)14-26(20,7)17(21)6/h8,10,13,17-21,23-24,28-29H,3,9,11-12,14H2,1-2,4-7H3/b13-10-,16-8-/t17-,18+,19-,20-,21+,23+,24-,26+/m0/s1
• InChI Key: RBNZUDGNUIATAX-GOEYFCEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₆
• Molecular Weight: 448.60 g/mol
• Exact Mass: 448.28248899 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	-	0.7349	73.49%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8708	87.08%
OATP1B3 inhibitior	+	0.8228	82.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7836	78.36%
P-glycoprotein inhibitior	+	0.5778	57.78%
P-glycoprotein substrate	+	0.5072	50.72%
CYP3A4 substrate	+	0.6975	69.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9016	90.16%
CYP3A4 inhibition	+	0.5716	57.16%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.7842	78.42%
CYP2D6 inhibition	-	0.9080	90.80%
CYP1A2 inhibition	-	0.8366	83.66%
CYP2C8 inhibition	+	0.4947	49.47%
CYP inhibitory promiscuity	-	0.8880	88.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.7016	70.16%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9632	96.32%
Skin irritation	+	0.5383	53.83%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7066	70.66%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5278	52.78%
skin sensitisation	-	0.7538	75.38%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6373	63.73%
Acute Oral Toxicity (c)	III	0.5073	50.73%
Estrogen receptor binding	+	0.6886	68.86%
Androgen receptor binding	-	0.5303	53.03%
Thyroid receptor binding	-	0.5260	52.60%
Glucocorticoid receptor binding	+	0.6453	64.53%
Aromatase binding	+	0.5943	59.43%
PPAR gamma	+	0.6074	60.74%
Honey bee toxicity	-	0.6468	64.68%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.70%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.91%	90.17%
CHEMBL204	P00734	Thrombin	95.88%	96.01%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.55%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.62%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	92.42%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	90.49%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.91%	96.77%
CHEMBL2581	P07339	Cathepsin D	89.57%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.70%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.04%	99.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.29%	96.38%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.00%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.04%	89.34%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.76%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.50%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.15%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.68%	94.33%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.54%	80.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.39%	97.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.75%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.10%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.02%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.96%	83.82%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.89%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.72%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.36%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.98%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.91%	96.47%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.44%	93.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.00%	89.05%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.00%	95.71%

Plants that contains it

• Senecio erubescens

Cross-Links

• PubChem: 163078787
• LOTUS: LTS0045164
• wikiData: Q105233210