[(1S,4aR,5S,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (1S,4aS,7R,7aR)-7-methyl-1-[(2S,3R,4S,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: 1647c70d-0f32-4e27-bd20-e55bd787e213
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5S,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (1S,4aS,7R,7aR)-7-methyl-1-[(2S,3R,4S,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(C4C(C3O)(CO)O)OC5C(C(C(C(O5)CO)O)O)O)OC6C(C(C(C(O6)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]4[C@@]([C@@H]3O)(CO)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C31H46O19/c1-10-2-3-11-13(8-45-27(16(10)11)49-29-22(39)20(37)18(35)14(6-32)46-29)26(42)48-24-12-4-5-44-28(17(12)31(43,9-34)25(24)41)50-30-23(40)21(38)19(36)15(7-33)47-30/h4-5,8,10-12,14-25,27-30,32-41,43H,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: RJKPJQSDIOKNPJ-IBTNOTJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₁₉
• Molecular Weight: 722.70 g/mol
• Exact Mass: 722.26332923 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -5.37
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6693	66.93%
Caco-2	-	0.8950	89.50%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7087	70.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7342	73.42%
OATP1B3 inhibitior	+	0.9158	91.58%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7629	76.29%
BSEP inhibitior	+	0.6062	60.62%
P-glycoprotein inhibitior	+	0.5885	58.85%
P-glycoprotein substrate	-	0.5897	58.97%
CYP3A4 substrate	+	0.6659	66.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.9593	95.93%
CYP2C9 inhibition	-	0.8950	89.50%
CYP2C19 inhibition	-	0.8913	89.13%
CYP2D6 inhibition	-	0.9164	91.64%
CYP1A2 inhibition	-	0.8711	87.11%
CYP2C8 inhibition	+	0.5729	57.29%
CYP inhibitory promiscuity	-	0.9060	90.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6226	62.26%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.6152	61.52%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5695	56.95%
Human Ether-a-go-go-Related Gene inhibition	+	0.7084	70.84%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8928	89.28%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4470	44.70%
Estrogen receptor binding	+	0.7807	78.07%
Androgen receptor binding	+	0.6448	64.48%
Thyroid receptor binding	-	0.5513	55.13%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5522	55.22%
PPAR gamma	+	0.6588	65.88%
Honey bee toxicity	-	0.8031	80.31%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.6853	68.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.42%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.65%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.86%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.16%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.54%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	90.89%	92.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.21%	94.80%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.08%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.80%	89.00%
CHEMBL4208	P20618	Proteasome component C5	85.51%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.60%	96.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.45%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.46%	95.56%

Plants that contains it

• Argylia radiata

Cross-Links

• PubChem: 101637171
• LOTUS: LTS0032047
• wikiData: Q105237563