[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(1S,4R,9R,10S,13R,15R)-15-hydroxy-5,5-dimethyl-14-methylidene-3-oxo-9-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-6-(hydroxymethyl)oxan-3-yl] acetate

Details

• Internal ID: c6022954-b8d2-4155-92d4-ae2c3aec5426
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(1S,4R,9R,10S,13R,15R)-15-hydroxy-5,5-dimethyl-14-methylidene-3-oxo-9-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methoxy]-6-(hydroxymethyl)oxan-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C(OC1OCC23CCCC(C2C(=O)CC45C3CCC(C4)C(=C)C5O)(C)C)CO)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC[C@@]23CCCC([C@H]2C(=O)C[C@]45[C@H]3CC[C@H](C4)C(=C)[C@H]5O)(C)C)CO)O)O
• InChI: InChI=1S/C28H42O9/c1-14-16-6-7-19-27(13-35-25-22(36-15(2)30)21(33)20(32)18(12-29)37-25)9-5-8-26(3,4)23(27)17(31)11-28(19,10-16)24(14)34/h16,18-25,29,32-34H,1,5-13H2,2-4H3/t16-,18-,19+,20-,21+,22-,23-,24-,25-,27-,28+/m1/s1
• InChI Key: RKYXYZPNMDCHNU-LPXGKBKBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₉
• Molecular Weight: 522.60 g/mol
• Exact Mass: 522.28288291 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7224	72.24%
Caco-2	-	0.7827	78.27%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8132	81.32%
OATP2B1 inhibitior	-	0.7137	71.37%
OATP1B1 inhibitior	+	0.8158	81.58%
OATP1B3 inhibitior	+	0.8369	83.69%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.8088	80.88%
P-glycoprotein inhibitior	-	0.5273	52.73%
P-glycoprotein substrate	-	0.6566	65.66%
CYP3A4 substrate	+	0.6990	69.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.8865	88.65%
CYP2C9 inhibition	-	0.6959	69.59%
CYP2C19 inhibition	-	0.8125	81.25%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.8093	80.93%
CYP2C8 inhibition	+	0.5187	51.87%
CYP inhibitory promiscuity	-	0.9247	92.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7275	72.75%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9227	92.27%
Skin irritation	-	0.5995	59.95%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7485	74.85%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5699	56.99%
skin sensitisation	-	0.8897	88.97%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4811	48.11%
Acute Oral Toxicity (c)	III	0.5840	58.40%
Estrogen receptor binding	+	0.6253	62.53%
Androgen receptor binding	+	0.6655	66.55%
Thyroid receptor binding	-	0.5436	54.36%
Glucocorticoid receptor binding	+	0.6185	61.85%
Aromatase binding	+	0.7046	70.46%
PPAR gamma	+	0.5287	52.87%
Honey bee toxicity	-	0.7761	77.61%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9893	98.93%

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	98.62%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.43%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.30%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.66%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.07%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	91.88%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	91.65%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	90.08%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	87.62%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.55%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.86%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.86%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.82%	93.04%
CHEMBL237	P41145	Kappa opioid receptor	84.73%	98.10%
CHEMBL2996	Q05655	Protein kinase C delta	84.12%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.75%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.40%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.02%	91.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.01%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.06%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.24%	92.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.78%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.57%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.51%	93.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.01%	82.50%

Plants that contains it

• Jungermannia infusca

Cross-Links

• PubChem: 102437301
• LOTUS: LTS0164867
• wikiData: Q105239662