[(1S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4S,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,7R,7aR)-7-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 71ca4ef8-76fb-4772-9a6b-5f8b940a167e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4S,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,7R,7aR)-7-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1CCC2C1C(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
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O[C@H]3[C@H]4C=CO[C@H]([C@@H]4C5([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
• InChI: InChI=1S/C31H44O18/c1-10-2-3-11-13(8-43-27(16(10)11)47-29-22(39)20(37)18(35)14(6-32)44-29)26(41)46-24-12-4-5-42-28(17(12)31(9-34)25(24)49-31)48-30-23(40)21(38)19(36)15(7-33)45-30/h4-5,8,10-12,14-25,27-30,32-40H,2-3,6-7,9H2,1H3/t10-,11-,12+,14-,15+,16-,17-,18-,19-,20-,21+,22+,23+,24+,25+,27+,28+,29+,30+,31?/m1/s1
• InChI Key: XYQGKOSSVPHSBW-FKQTWKFGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₈
• Molecular Weight: 704.70 g/mol
• Exact Mass: 704.25276455 g/mol
• Topological Polar Surface Area (TPSA): 276.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -4.32
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6481	64.81%
Caco-2	-	0.8944	89.44%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7396	73.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7290	72.90%
OATP1B3 inhibitior	+	0.9232	92.32%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.7846	78.46%
BSEP inhibitior	+	0.5799	57.99%
P-glycoprotein inhibitior	+	0.5990	59.90%
P-glycoprotein substrate	-	0.5522	55.22%
CYP3A4 substrate	+	0.6842	68.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.9666	96.66%
CYP2C9 inhibition	-	0.8331	83.31%
CYP2C19 inhibition	-	0.8503	85.03%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.8238	82.38%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	-	0.8341	83.41%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6269	62.69%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9284	92.84%
Skin irritation	-	0.6630	66.30%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	-	0.5424	54.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7545	75.45%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8641	86.41%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.4091	40.91%
Estrogen receptor binding	+	0.7872	78.72%
Androgen receptor binding	+	0.6609	66.09%
Thyroid receptor binding	-	0.5411	54.11%
Glucocorticoid receptor binding	-	0.4714	47.14%
Aromatase binding	+	0.5462	54.62%
PPAR gamma	+	0.6698	66.98%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.7725	77.25%

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	98.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.40%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.23%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.99%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.29%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	91.23%	92.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.15%	96.21%
CHEMBL4040	P28482	MAP kinase ERK2	89.67%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.22%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.81%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.72%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.25%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.74%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.58%	94.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.18%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.13%	85.14%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.21%	83.57%
CHEMBL4208	P20618	Proteasome component C5	82.07%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.14%	91.24%

Plants that contains it

• Argylia radiata

Cross-Links

• PubChem: 163193974
• LOTUS: LTS0028086
• wikiData: Q105344618