PlantaeDB Logo
Login Sign-up

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

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID 5c74be10-1bb6-4bbc-ad91-5530b15a7a1a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,6R,7R,7aR)-4-methoxycarbonyl-7-methyl-1-[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl] (1R,4aS,6S,7S,7aS)-6-hydroxy-7-methyl-1-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OC3CC4C(C3C)C(OC=C4C(=O)OC)OC5C(C(C(C(O5)CO)O)O)O)OC6C(C(C(C(O6)CO)O)O)O)O
SMILES (Isomeric) C[C@@H]1[C@H](C[C@H]2[C@@H]1[C@H](OC=C2C(=O)O[C@@H]3C[C@@H]4[C@H]([C@H]3C)[C@@H](OC=C4C(=O)OC)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)O
InChI InChI=1S/C33H48O19/c1-10-16(36)4-12-15(9-47-30(20(10)12)51-32-26(41)24(39)22(37)18(6-34)49-32)29(44)48-17-5-13-14(28(43)45-3)8-46-31(21(13)11(17)2)52-33-27(42)25(40)23(38)19(7-35)50-33/h8-13,16-27,30-42H,4-7H2,1-3H3/t10-,11+,12-,13+,16+,17-,18+,19-,20-,21+,22+,23+,24+,25-,26+,27+,30-,31+,32-,33-/m1/s1
InChI Key RFGKYBWBAYNUAA-NMUMBVHQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C33H48O19
Molecular Weight 748.70 g/mol
Exact Mass 748.27897930 g/mol
Topological Polar Surface Area (TPSA) 290.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -3.91
H-Bond Acceptor 19
H-Bond Donor 9
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(1S,4aR,6R,7R,7aR)-4-methoxycarbonyl-7-methyl-1-[(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl] (1R,4aS,6S,7S,7aS)-6-hydroxy-7-methyl-1-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5731 57.31%
Caco-2 - 0.8877 88.77%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.5792 57.92%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.5248 52.48%
OATP1B3 inhibitior + 0.9447 94.47%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.6689 66.89%
P-glycoprotein inhibitior + 0.6073 60.73%
P-glycoprotein substrate - 0.6332 63.32%
CYP3A4 substrate + 0.6526 65.26%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8671 86.71%
CYP3A4 inhibition - 0.9228 92.28%
CYP2C9 inhibition - 0.9216 92.16%
CYP2C19 inhibition - 0.9191 91.91%
CYP2D6 inhibition - 0.9209 92.09%
CYP1A2 inhibition - 0.9004 90.04%
CYP2C8 inhibition + 0.4767 47.67%
CYP inhibitory promiscuity - 0.9353 93.53%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6942 69.42%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.9244 92.44%
Skin irritation - 0.7299 72.99%
Skin corrosion - 0.9465 94.65%
Ames mutagenesis - 0.5054 50.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7493 74.93%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7250 72.50%
skin sensitisation - 0.8832 88.32%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.6854 68.54%
Acute Oral Toxicity (c) III 0.5515 55.15%
Estrogen receptor binding + 0.8002 80.02%
Androgen receptor binding + 0.6330 63.30%
Thyroid receptor binding - 0.5423 54.23%
Glucocorticoid receptor binding + 0.6177 61.77%
Aromatase binding - 0.4831 48.31%
PPAR gamma + 0.6801 68.01%
Honey bee toxicity - 0.8199 81.99%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity - 0.3988 39.88%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.25% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.15% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.22% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.94% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 91.34% 94.73%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.20% 86.92%
CHEMBL4208 P20618 Proteasome component C5 88.96% 90.00%
CHEMBL4040 P28482 MAP kinase ERK2 88.49% 83.82%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.42% 99.17%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 87.84% 95.83%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.53% 96.00%
CHEMBL2581 P07339 Cathepsin D 81.99% 98.95%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.69% 94.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.44% 89.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.96% 91.24%

Plants that contains it

Top
Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Strychnos lucida

Cross-Links

Top
PubChem 163036931
LOTUS LTS0273372
wikiData Q105235387