[(1R,4S,9R,12S,13S,16R,17R,18R)-17-(hydroxymethyl)-12-methyl-7-oxo-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadec-5-en-18-yl] acetate

Details

• Internal ID: 7062132f-f48f-4abe-b3e2-b0c553d3e28b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(1R,4S,9R,12S,13S,16R,17R,18R)-17-(hydroxymethyl)-12-methyl-7-oxo-17-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadec-5-en-18-yl] acetate
• SMILES (Canonical): CC(=O)OC1C23CCC4C5=CC(=O)OC5CCC4(C2CCC(C3)C1(CO)OC6C(C(C(C(O6)CO)O)O)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@]23CC[C@@H]4C5=CC(=O)O[C@@H]5CC[C@]4([C@@H]2CC[C@H](C3)[C@]1(CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C
• InChI: InChI=1S/C28H40O11/c1-13(31)36-25-27-8-5-16-15-9-20(32)37-17(15)6-7-26(16,2)19(27)4-3-14(10-27)28(25,12-30)39-24-23(35)22(34)21(33)18(11-29)38-24/h9,14,16-19,21-25,29-30,33-35H,3-8,10-12H2,1-2H3/t14-,16-,17-,18-,19+,21-,22+,23-,24+,25-,26-,27-,28+/m1/s1
• InChI Key: BPBHKHLPQTYQOU-YQSHXZEHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₁₁
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.25706209 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.06
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7664	76.64%
Caco-2	-	0.8534	85.34%
Blood Brain Barrier	-	0.6161	61.61%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8638	86.38%
OATP2B1 inhibitior	-	0.7230	72.30%
OATP1B1 inhibitior	+	0.8340	83.40%
OATP1B3 inhibitior	+	0.9022	90.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	-	0.5710	57.10%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6058	60.58%
CYP3A4 substrate	+	0.7031	70.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8917	89.17%
CYP3A4 inhibition	-	0.9277	92.77%
CYP2C9 inhibition	-	0.8683	86.83%
CYP2C19 inhibition	-	0.8970	89.70%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	-	0.8512	85.12%
CYP2C8 inhibition	+	0.4489	44.89%
CYP inhibitory promiscuity	-	0.9226	92.26%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5673	56.73%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9376	93.76%
Skin irritation	-	0.5698	56.98%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8219	82.19%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9184	91.84%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7450	74.50%
Acute Oral Toxicity (c)	III	0.4846	48.46%
Estrogen receptor binding	+	0.8063	80.63%
Androgen receptor binding	+	0.6750	67.50%
Thyroid receptor binding	-	0.5999	59.99%
Glucocorticoid receptor binding	+	0.5965	59.65%
Aromatase binding	+	0.6771	67.71%
PPAR gamma	+	0.6249	62.49%
Honey bee toxicity	-	0.7590	75.90%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9766	97.66%

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	98.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.93%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.48%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.43%	100.00%
CHEMBL2581	P07339	Cathepsin D	87.40%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	87.17%	94.75%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.66%	96.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.35%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.22%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.07%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.73%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.20%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.10%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.99%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	83.03%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.37%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.16%	93.04%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.67%	95.71%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.02%	82.38%

Plants that contains it

• Diplospora dubia

Cross-Links

• PubChem: 20056363
• LOTUS: LTS0272271
• wikiData: Q104941354