(1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid 4-beta-D-glucopyranosyl ester

Details

• Internal ID: ef052367-46d2-4efc-b0a0-96829772320a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid
• SMILES (Canonical): C1CC(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC4C(C(C(C(O4)CO)O)O)O)C(=O)O
• SMILES (Isomeric): C1C[C@@H]([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=O)O
• InChI: InChI=1S/C22H32O16/c23-3-9-12(25)14(27)16(29)21(35-9)37-19(33)8-5-34-20(11-6(8)1-2-7(11)18(31)32)38-22-17(30)15(28)13(26)10(4-24)36-22/h5-7,9-17,20-30H,1-4H2,(H,31,32)/t6-,7+,9-,10-,11+,12-,13-,14+,15+,16-,17-,20+,21+,22+/m1/s1
• InChI Key: QRQZCZAAURIHIG-HXNDVIFYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₁₆
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.16903493 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -4.89
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6649	66.49%
Caco-2	-	0.9043	90.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7676	76.76%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.7365	73.65%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8640	86.40%
P-glycoprotein inhibitior	-	0.6772	67.72%
P-glycoprotein substrate	-	0.9036	90.36%
CYP3A4 substrate	+	0.5735	57.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.9455	94.55%
CYP2C9 inhibition	-	0.8689	86.89%
CYP2C19 inhibition	-	0.8590	85.90%
CYP2D6 inhibition	-	0.9020	90.20%
CYP1A2 inhibition	-	0.8599	85.99%
CYP2C8 inhibition	-	0.5637	56.37%
CYP inhibitory promiscuity	-	0.8727	87.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6783	67.83%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.7901	79.01%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4612	46.12%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.8352	83.52%
skin sensitisation	-	0.8826	88.26%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6778	67.78%
Acute Oral Toxicity (c)	III	0.4056	40.56%
Estrogen receptor binding	+	0.6564	65.64%
Androgen receptor binding	+	0.6140	61.40%
Thyroid receptor binding	-	0.6165	61.65%
Glucocorticoid receptor binding	-	0.6272	62.72%
Aromatase binding	-	0.4871	48.71%
PPAR gamma	+	0.5566	55.66%
Honey bee toxicity	-	0.8843	88.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.5000	50.00%

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	96.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.01%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	90.44%	94.23%
CHEMBL5255	O00206	Toll-like receptor 4	86.54%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.75%	99.17%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	84.25%	94.97%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.65%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.22%	96.61%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.97%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.87%	89.00%

Plants that contains it

• Acacia kempeana
• Aframomum sulcatum
• Alhagi pseudalhagi subsp. persarum
• Baillonella toxisperma
• Castanopsis cuspidata
• Centaurea axillaris
• Decaisnea fargesii
• Dendrobium crepidatum
• Dendrobium thyrsiflorum
• Diospyros buxifolia
• Forsythia viridissima
• Hymenaea courbaril
• Laburnum watereri
• Lessertia frutescens
• Montanoa guatemalensis
• Polygonatum stenophyllum
• Pteris biaurita subsp. fornicata
• Senecio variabilis
• Teucrium lanigerum

Cross-Links

• PubChem: 101673969
• NPASS: NPC128283
• LOTUS: LTS0135849
• wikiData: Q105226569