[(4aR,5S,8R,8aR)-8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-8-yl] (E,2R,3S,6R)-3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate

Details

• Internal ID: 18b98939-952a-4460-8a4c-d947a3023610
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(4aR,5S,8R,8aR)-8a-hydroxy-3,4a,5-trimethyl-2-oxo-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-8-yl] (E,2R,3S,6R)-3-hydroxy-6-(hydroxymethyl)-2,4-dimethyldodec-4-enoate
• SMILES (Canonical): CCCCCCC(CO)C=C(C)C(C(C)C(=O)OC1CCC(C2(C1(C=C3C(=C(C(=O)O3)C)C2)O)C)C)O
• SMILES (Isomeric): CCCCCC[C@@H](CO)/C=C(\C)/[C@H]([C@@H](C)C(=O)O[C@@H]1CC[C@@H]([C@@]2([C@@]1(C=C3C(=C(C(=O)O3)C)C2)O)C)C)O
• InChI: InChI=1S/C30H46O7/c1-7-8-9-10-11-22(17-31)14-18(2)26(32)21(5)28(34)37-25-13-12-19(3)29(6)15-23-20(4)27(33)36-24(23)16-30(25,29)35/h14,16,19,21-22,25-26,31-32,35H,7-13,15,17H2,1-6H3/b18-14+/t19-,21+,22+,25+,26+,29+,30-/m0/s1
• InChI Key: KFAAXPBWXDDAGK-OXPDNWIKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₇
• Molecular Weight: 518.70 g/mol
• Exact Mass: 518.32435380 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.75
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	-	0.6846	68.46%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8281	82.81%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8635	86.35%
OATP1B3 inhibitior	+	0.9200	92.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5114	51.14%
BSEP inhibitior	+	0.8960	89.60%
P-glycoprotein inhibitior	+	0.7348	73.48%
P-glycoprotein substrate	+	0.6561	65.61%
CYP3A4 substrate	+	0.7123	71.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9045	90.45%
CYP3A4 inhibition	+	0.7160	71.60%
CYP2C9 inhibition	-	0.7420	74.20%
CYP2C19 inhibition	-	0.8510	85.10%
CYP2D6 inhibition	-	0.9328	93.28%
CYP1A2 inhibition	-	0.7332	73.32%
CYP2C8 inhibition	+	0.6351	63.51%
CYP inhibitory promiscuity	-	0.6783	67.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4471	44.71%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9257	92.57%
Skin irritation	+	0.7027	70.27%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4333	43.33%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5674	56.74%
skin sensitisation	-	0.9456	94.56%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6895	68.95%
Acute Oral Toxicity (c)	III	0.5823	58.23%
Estrogen receptor binding	+	0.7088	70.88%
Androgen receptor binding	+	0.6418	64.18%
Thyroid receptor binding	-	0.5421	54.21%
Glucocorticoid receptor binding	+	0.7589	75.89%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.5655	56.55%
Honey bee toxicity	-	0.8322	83.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5808	58.08%
Fish aquatic toxicity	+	0.9936	99.36%

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	98.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.12%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.23%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	96.01%	98.03%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.69%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.51%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	94.35%	97.79%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.27%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.68%	96.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.64%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.41%	92.86%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.08%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.73%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.39%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.90%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.68%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	89.33%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.29%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.99%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.64%	90.08%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	87.23%	91.81%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.98%	97.29%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.52%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.99%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.32%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.27%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.15%	95.89%

Plants that contains it

• Podocarpus macrophyllus

Cross-Links

• PubChem: 162986807
• LOTUS: LTS0231397
• wikiData: Q105140278