[(2R,3R,4R,5R,6S)-2-[(3S)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentoxy]-4,5-dihydroxy-6-methyloxan-3-yl] acetate

Details

• Internal ID: a9f7dfb7-6c29-4ab6-a129-8c1cfdc8cdfc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3R,4R,5R,6S)-2-[(3S)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentoxy]-4,5-dihydroxy-6-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OCCC(C)CCC2C(=C)CCC3C2(CCCC3(C)C)C)OC(=O)C)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OCC[C@@H](C)CC[C@@H]2C(=C)CC[C@H]3[C@]2(CCCC3(C)C)C)OC(=O)C)O)O
• InChI: InChI=1S/C28H48O6/c1-17(13-16-32-26-25(34-20(4)29)24(31)23(30)19(3)33-26)9-11-21-18(2)10-12-22-27(5,6)14-8-15-28(21,22)7/h17,19,21-26,30-31H,2,8-16H2,1,3-7H3/t17-,19-,21+,22+,23-,24+,25+,26+,28-/m0/s1
• InChI Key: PKESFOWCFUJEIO-MJZVDEJTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₈O₆
• Molecular Weight: 480.70 g/mol
• Exact Mass: 480.34508925 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.01
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9265	92.65%
Caco-2	-	0.7357	73.57%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7942	79.42%
OATP2B1 inhibitior	-	0.5675	56.75%
OATP1B1 inhibitior	+	0.8469	84.69%
OATP1B3 inhibitior	+	0.8075	80.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5181	51.81%
P-glycoprotein inhibitior	-	0.4372	43.72%
P-glycoprotein substrate	-	0.6569	65.69%
CYP3A4 substrate	+	0.6921	69.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8832	88.32%
CYP3A4 inhibition	-	0.8398	83.98%
CYP2C9 inhibition	-	0.8169	81.69%
CYP2C19 inhibition	-	0.7812	78.12%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.5450	54.50%
CYP2C8 inhibition	+	0.4450	44.50%
CYP inhibitory promiscuity	-	0.9189	91.89%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.5832	58.32%
Skin corrosion	-	0.9524	95.24%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6472	64.72%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6476	64.76%
skin sensitisation	-	0.7858	78.58%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8250	82.50%
Acute Oral Toxicity (c)	III	0.6582	65.82%
Estrogen receptor binding	+	0.5571	55.71%
Androgen receptor binding	+	0.5518	55.18%
Thyroid receptor binding	-	0.5308	53.08%
Glucocorticoid receptor binding	+	0.5821	58.21%
Aromatase binding	+	0.5194	51.94%
PPAR gamma	-	0.5101	51.01%
Honey bee toxicity	-	0.8072	80.72%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9914	99.14%

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	97.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.71%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.06%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.55%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.58%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.38%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	85.20%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.58%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.24%	89.00%
CHEMBL237	P41145	Kappa opioid receptor	84.15%	98.10%
CHEMBL340	P08684	Cytochrome P450 3A4	83.52%	91.19%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.51%	89.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.39%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	81.90%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.33%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.06%	100.00%
CHEMBL5028	O14672	ADAM10	80.99%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.89%	96.38%
CHEMBL1977	P11473	Vitamin D receptor	80.44%	99.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.12%	90.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.01%	95.50%

Plants that contains it

• Mimosa tenuiflora

Cross-Links

• PubChem: 101427307
• LOTUS: LTS0266694
• wikiData: Q105210374