methyl (3R)-1-methyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(6S,7R)-6-hydroxy-4-methoxycarbonyl-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]oxan-2-yl]methoxy]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate

Details

• Internal ID: 891ffe3f-1b07-46dc-99dc-c609afeb2adf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (3R)-1-methyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(6S,7R)-6-hydroxy-4-methoxycarbonyl-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]oxan-2-yl]methoxy]-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC4CC5C(C(O4)C)C(OC=C5C(=O)OC)OC6C(C(C(C(O6)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](CC2C1C(OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4CC5C(C(O4)C)C(OC=C5C(=O)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C34H50O20/c1-11-17(36)5-13-15(29(43)45-3)8-48-31(21(11)13)53-34-28(42)26(40)24(38)19(52-34)10-47-20-6-14-16(30(44)46-4)9-49-32(22(14)12(2)50-20)54-33-27(41)25(39)23(37)18(7-35)51-33/h8-9,11-14,17-28,31-42H,5-7,10H2,1-4H3/t11-,12?,13?,14?,17-,18+,19+,20+,21?,22?,23+,24+,25-,26-,27+,28+,31?,32?,33-,34-/m0/s1
• InChI Key: PVQSSYWOIOEIPR-IBTLDZGLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₀O₂₀
• Molecular Weight: 778.70 g/mol
• Exact Mass: 778.28954398 g/mol
• Topological Polar Surface Area (TPSA): 288.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -3.53
• H-Bond Acceptor: 20
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5758	57.58%
Caco-2	-	0.8778	87.78%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6327	63.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4598	45.98%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5132	51.32%
P-glycoprotein inhibitior	+	0.6754	67.54%
P-glycoprotein substrate	-	0.5618	56.18%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8671	86.71%
CYP3A4 inhibition	-	0.8657	86.57%
CYP2C9 inhibition	-	0.9319	93.19%
CYP2C19 inhibition	-	0.9113	91.13%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	-	0.9026	90.26%
CYP2C8 inhibition	+	0.4700	47.00%
CYP inhibitory promiscuity	-	0.9448	94.48%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6749	67.49%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9157	91.57%
Skin irritation	-	0.7185	71.85%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.5208	52.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7017	70.17%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6948	69.48%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7266	72.66%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	+	0.7918	79.18%
Androgen receptor binding	+	0.5739	57.39%
Thyroid receptor binding	-	0.5329	53.29%
Glucocorticoid receptor binding	+	0.6949	69.49%
Aromatase binding	+	0.6072	60.72%
PPAR gamma	+	0.7094	70.94%
Honey bee toxicity	-	0.7938	79.38%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7784	77.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.76%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.14%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.16%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.41%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	90.72%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.43%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.11%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.02%	90.00%
CHEMBL2581	P07339	Cathepsin D	86.89%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.84%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.82%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.49%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.09%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.98%	96.00%

Plants that contains it

• Cornus officinalis

Cross-Links

• PubChem: 24883586
• NPASS: NPC49771