[(2S,3S,4aS,5R,8aS)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 6e0b3cc4-70c7-4b77-bc11-8e120da1a279
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3S,4aS,5R,8aS)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(CC2(C(C1(C)C)CC=C(C2CCC(=CCO)C)C)C)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H](C[C@@]2([C@@H](C1(C)C)CC=C([C@H]2CC/C(=C/CO)/C)C)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C31H50O9/c1-8-18(3)28(37)40-27-21(38-29-26(36)25(35)24(34)22(16-33)39-29)15-31(7)20(11-9-17(2)13-14-32)19(4)10-12-23(31)30(27,5)6/h8,10,13,20-27,29,32-36H,9,11-12,14-16H2,1-7H3/b17-13+,18-8-/t20-,21+,22-,23-,24-,25+,26-,27-,29-,31+/m1/s1
• InChI Key: PLDRHISOSDFQSZ-UVOAKBLPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₉
• Molecular Weight: 566.70 g/mol
• Exact Mass: 566.34548317 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7315	73.15%
Caco-2	-	0.7869	78.69%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.8515	85.15%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8211	82.11%
OATP1B3 inhibitior	-	0.3666	36.66%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8664	86.64%
P-glycoprotein inhibitior	+	0.6847	68.47%
P-glycoprotein substrate	-	0.6819	68.19%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	-	0.8033	80.33%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.9412	94.12%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.8290	82.90%
CYP2D6 inhibition	-	0.9369	93.69%
CYP1A2 inhibition	-	0.7750	77.50%
CYP2C8 inhibition	+	0.5556	55.56%
CYP inhibitory promiscuity	-	0.9174	91.74%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7095	70.95%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.6802	68.02%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7501	75.01%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7842	78.42%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.5934	59.34%
Acute Oral Toxicity (c)	III	0.7411	74.11%
Estrogen receptor binding	+	0.7307	73.07%
Androgen receptor binding	+	0.6128	61.28%
Thyroid receptor binding	-	0.5284	52.84%
Glucocorticoid receptor binding	+	0.7025	70.25%
Aromatase binding	+	0.6815	68.15%
PPAR gamma	+	0.6704	67.04%
Honey bee toxicity	-	0.6666	66.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9623	96.23%

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	98.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.47%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.83%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.92%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	91.51%	94.73%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.22%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.15%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.72%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.62%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.27%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.03%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.68%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.91%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.95%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.24%	93.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.53%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.06%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.23%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.76%	89.00%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 102060701
• LOTUS: LTS0038380
• wikiData: Q105210838