(1R,4aR,7R,7aR)-7-[[4-[[(1R,4aR,7R,7aR)-4-carboxy-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl]methoxycarbonyl]-2,5-dihydroxybenzoyl]oxymethyl]-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: e4f089c2-9629-44b5-808e-dd9bd3418563
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1R,4aR,7R,7aR)-7-[[4-[[(1R,4aR,7R,7aR)-4-carboxy-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl]methoxycarbonyl]-2,5-dihydroxybenzoyl]oxymethyl]-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1CC2C(C1COC(=O)C3=CC(=C(C=C3O)C(=O)OCC4CCC5C4C(OC=C5C(=O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C(OC=C2C(=O)O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C1C[C@@H]2[C@H]([C@@H]1COC(=O)C3=CC(=C(C=C3O)C(=O)OC[C@@H]4CC[C@@H]5[C@H]4[C@H](OC=C5C(=O)O)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO)O)O)O)O)[C@H](OC=C2C(=O)O)O[C@@H]7[C@H]([C@@H]([C@H]([C@@H](O7)CO)O)O)O
• InChI: InChI=1S/C40H50O24/c41-7-23-27(45)29(47)31(49)39(61-23)63-37-25-13(1-3-15(25)19(11-59-37)33(51)52)9-57-35(55)17-5-22(44)18(6-21(17)43)36(56)58-10-14-2-4-16-20(34(53)54)12-60-38(26(14)16)64-40-32(50)30(48)28(46)24(8-42)62-40/h5-6,11-16,23-32,37-50H,1-4,7-10H2,(H,51,52)(H,53,54)/t13-,14-,15-,16-,23-,24-,25-,26-,27-,28-,29+,30+,31-,32-,37+,38+,39+,40+/m0/s1
• InChI Key: NKBVVLGVRPWDKV-HFASPTNUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₀O₂₄
• Molecular Weight: 914.80 g/mol
• Exact Mass: 914.26920246 g/mol
• Topological Polar Surface Area (TPSA): 385.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -3.02
• H-Bond Acceptor: 22
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5889	58.89%
Caco-2	-	0.8670	86.70%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7554	75.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7153	71.53%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9321	93.21%
P-glycoprotein inhibitior	+	0.7342	73.42%
P-glycoprotein substrate	-	0.8149	81.49%
CYP3A4 substrate	+	0.5647	56.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8737	87.37%
CYP3A4 inhibition	-	0.8818	88.18%
CYP2C9 inhibition	-	0.8276	82.76%
CYP2C19 inhibition	-	0.6605	66.05%
CYP2D6 inhibition	-	0.8399	83.99%
CYP1A2 inhibition	-	0.5965	59.65%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8136	81.36%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6923	69.23%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8997	89.97%
Skin irritation	-	0.8073	80.73%
Skin corrosion	-	0.9584	95.84%
Ames mutagenesis	-	0.6240	62.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7908	79.08%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8228	82.28%
skin sensitisation	-	0.8165	81.65%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7458	74.58%
Acute Oral Toxicity (c)	III	0.4397	43.97%
Estrogen receptor binding	+	0.7279	72.79%
Androgen receptor binding	+	0.7051	70.51%
Thyroid receptor binding	+	0.5585	55.85%
Glucocorticoid receptor binding	+	0.6374	63.74%
Aromatase binding	-	0.5056	50.56%
PPAR gamma	+	0.7459	74.59%
Honey bee toxicity	-	0.8745	87.45%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.9554	95.54%

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	98.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.37%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.30%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	90.99%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.45%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.32%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.24%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.24%	86.92%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.12%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.88%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.36%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.40%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.02%	95.89%
CHEMBL3194	P02766	Transthyretin	81.02%	90.71%

Plants that contains it

• Fagraea blumei

Cross-Links

• PubChem: 162997011
• LOTUS: LTS0270958
• wikiData: Q105180445