[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: a962b5fa-8d80-405b-9c80-7b0dd5da8131
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (1S,4aS,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)OC3C4C=COC(C4C5(C3O5)CO)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O[C@H]3[C@H]4C=CO[C@H]([C@@H]4[C@@]5([C@H]3O5)CO)O[C@H]6[C@H]([C@@H]([C@@H]([C@@H](O6)CO)O)O)O)O[C@H]7[C@H]([C@H]([C@@H]([C@@H](O7)CO)O)O)O)O
• InChI: InChI=1S/C31H44O19/c1-30(42)4-2-10-12(8-44-26(15(10)30)48-28-21(39)19(37)17(35)13(6-32)45-28)25(41)47-23-11-3-5-43-27(16(11)31(9-34)24(23)50-31)49-29-22(40)20(38)18(36)14(7-33)46-29/h3,5,8,10-11,13-24,26-29,32-40,42H,2,4,6-7,9H2,1H3/t10-,11+,13+,14+,15-,16-,17-,18-,19+,20-,21+,22+,23+,24+,26+,27+,28+,29+,30+,31-/m1/s1
• InChI Key: YCBWBUAFHXKISV-CSVPLBATSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₉
• Molecular Weight: 720.70 g/mol
• Exact Mass: 720.24767917 g/mol
• Topological Polar Surface Area (TPSA): 297.00 Ų
• XlogP: -4.40
• Atomic LogP (AlogP): -5.21
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6893	68.93%
Caco-2	-	0.8956	89.56%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6845	68.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7366	73.66%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7629	76.29%
BSEP inhibitior	-	0.5389	53.89%
P-glycoprotein inhibitior	+	0.6173	61.73%
P-glycoprotein substrate	-	0.6055	60.55%
CYP3A4 substrate	+	0.7075	70.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	-	0.9483	94.83%
CYP2C9 inhibition	-	0.8383	83.83%
CYP2C19 inhibition	-	0.8566	85.66%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8520	85.20%
CYP2C8 inhibition	+	0.5939	59.39%
CYP inhibitory promiscuity	-	0.9023	90.23%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6239	62.39%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.6370	63.70%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7532	75.32%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7914	79.14%
skin sensitisation	-	0.8661	86.61%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6190	61.90%
Acute Oral Toxicity (c)	I	0.4433	44.33%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.6828	68.28%
Thyroid receptor binding	-	0.5360	53.60%
Glucocorticoid receptor binding	+	0.5518	55.18%
Aromatase binding	+	0.5769	57.69%
PPAR gamma	+	0.6798	67.98%
Honey bee toxicity	-	0.7987	79.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.6955	69.55%

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	97.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.16%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.44%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.87%	97.25%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.51%	83.57%
CHEMBL5255	O00206	Toll-like receptor 4	89.50%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.03%	96.21%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.38%	94.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.32%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.90%	86.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.20%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.05%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.51%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.09%	86.92%
CHEMBL4208	P20618	Proteasome component C5	83.96%	90.00%
CHEMBL2581	P07339	Cathepsin D	83.85%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.50%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.34%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.34%	95.83%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.67%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.34%	95.89%

Plants that contains it

• Argylia radiata

Cross-Links

• PubChem: 163106684
• LOTUS: LTS0074823
• wikiData: Q105346184