[(1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-2,3,4,4a,5,8-hexahydro-1H-naphthalen-2-yl] (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate

Details

• Internal ID: 44e2fc80-8fdb-451b-8892-0cd8d264929e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-2,3,4,4a,5,8-hexahydro-1H-naphthalen-2-yl] (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate
• SMILES (Canonical): CCCCCC=CC(=CC=CC(=O)OC1CCC2C(C(=O)C(=C(C)CO)CC2(C1C)C)O)C
• SMILES (Isomeric): CCCCC/C=C/C(=C/C=C/C(=O)O[C@@H]1CC[C@H]2[C@@H](C(=O)/C(=C(\C)/CO)/C[C@@]2([C@H]1C)C)O)/C
• InChI: InChI=1S/C28H42O5/c1-6-7-8-9-10-12-19(2)13-11-14-25(30)33-24-16-15-23-27(32)26(31)22(20(3)18-29)17-28(23,5)21(24)4/h10-14,21,23-24,27,29,32H,6-9,15-18H2,1-5H3/b12-10+,14-11+,19-13+,22-20+/t21-,23-,24+,27-,28+/m0/s1
• InChI Key: HVMGZGISBALRNN-XPGLAVBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₅
• Molecular Weight: 458.60 g/mol
• Exact Mass: 458.30322444 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 5.23
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	-	0.5720	57.20%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8868	88.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8069	80.69%
OATP1B3 inhibitior	+	0.8766	87.66%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6233	62.33%
BSEP inhibitior	+	0.9053	90.53%
P-glycoprotein inhibitior	+	0.7464	74.64%
P-glycoprotein substrate	-	0.5082	50.82%
CYP3A4 substrate	+	0.7190	71.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9108	91.08%
CYP3A4 inhibition	+	0.5524	55.24%
CYP2C9 inhibition	-	0.8590	85.90%
CYP2C19 inhibition	-	0.9015	90.15%
CYP2D6 inhibition	-	0.8941	89.41%
CYP1A2 inhibition	-	0.8689	86.89%
CYP2C8 inhibition	+	0.5265	52.65%
CYP inhibitory promiscuity	-	0.7631	76.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6910	69.10%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9619	96.19%
Skin irritation	+	0.5203	52.03%
Skin corrosion	-	0.9743	97.43%
Ames mutagenesis	-	0.7737	77.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7705	77.05%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5056	50.56%
skin sensitisation	-	0.9043	90.43%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8947	89.47%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4826	48.26%
Acute Oral Toxicity (c)	III	0.5868	58.68%
Estrogen receptor binding	+	0.7294	72.94%
Androgen receptor binding	+	0.5769	57.69%
Thyroid receptor binding	+	0.5314	53.14%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	+	0.5531	55.31%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8669	86.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5848	58.48%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.55%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.99%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.50%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.71%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.37%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.72%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	90.80%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.41%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	89.78%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.72%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.43%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.41%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.72%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.72%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.43%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.22%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.84%	89.00%
CHEMBL2664	P23526	Adenosylhomocysteinase	82.78%	86.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.05%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.05%	91.71%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.02%	94.66%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.14%	96.00%
CHEMBL1902	P62942	FK506-binding protein 1A	80.81%	97.05%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.40%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.14%	95.50%

Plants that contains it

• Senecio macrocephalus

Cross-Links

• PubChem: 162955830
• LOTUS: LTS0265791
• wikiData: Q105034352