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methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-4-[(E)-3-[(2S,3R,4R)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-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-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]-4-oxobut-2-enyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-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

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

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Internal ID 26cf0bfa-5c48-4407-9bae-bb2f24dd3cae
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-4-[(E)-3-[(2S,3R,4R)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-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-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]-4-oxobut-2-enyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-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) CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=COC(C(C4CC=C(C=O)C5C(C(OC=C5C(=O)OC6CC7C(C6C)C(OC=C7C(=O)OC)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C=C)C=C)OC1C(C(C(C(O1)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CO[C@H]([C@@H]([C@@H]4C/C=C(/C=O)\[C@H]5[C@H]([C@@H](OC=C5C(=O)O[C@H]6C[C@H]7[C@@H]([C@H]6C)[C@@H](OC=C7C(=O)OC)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)C=C)C=C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI InChI=1S/C66H90O37/c1-7-25-27(30(18-90-59(25)100-63-51(80)47(76)43(72)36(14-68)96-63)57(86)94-34-11-28-31(55(84)88-5)19-92-61(40(28)22(34)3)102-65-53(82)49(78)45(74)38(16-70)98-65)10-9-24(13-67)42-26(8-2)60(101-64-52(81)48(77)44(73)37(15-69)97-64)91-21-33(42)58(87)95-35-12-29-32(56(85)89-6)20-93-62(41(29)23(35)4)103-66-54(83)50(79)46(75)39(17-71)99-66/h7-9,13,18-23,25-29,34-54,59-66,68-83H,1-2,10-12,14-17H2,3-6H3/b24-9-/t22-,23-,25+,26+,27-,28+,29+,34-,35-,36+,37+,38+,39+,40+,41+,42-,43+,44+,45+,46+,47-,48-,49-,50-,51+,52+,53+,54+,59-,60-,61-,62-,63-,64-,65-,66-/m0/s1
InChI Key JGFCDHIJCNLFPY-WSMFPRBZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C66H90O37
Molecular Weight 1475.40 g/mol
Exact Mass 1474.5160938 g/mol
Topological Polar Surface Area (TPSA) 557.00 Ų
XlogP -4.00
Atomic LogP (AlogP) -6.72
H-Bond Acceptor 37
H-Bond Donor 16
Rotatable Bonds 24

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-4-[(E)-3-[(2S,3R,4R)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-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-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]-4-oxobut-2-enyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-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

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4943 49.43%
Caco-2 - 0.8589 85.89%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.6249 62.49%
OATP2B1 inhibitior - 0.8645 86.45%
OATP1B1 inhibitior + 0.7128 71.28%
OATP1B3 inhibitior + 0.9286 92.86%
MATE1 inhibitior - 0.8812 88.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9546 95.46%
P-glycoprotein inhibitior + 0.7434 74.34%
P-glycoprotein substrate + 0.5945 59.45%
CYP3A4 substrate + 0.7166 71.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8763 87.63%
CYP3A4 inhibition - 0.8789 87.89%
CYP2C9 inhibition - 0.8962 89.62%
CYP2C19 inhibition - 0.8695 86.95%
CYP2D6 inhibition - 0.9277 92.77%
CYP1A2 inhibition - 0.8934 89.34%
CYP2C8 inhibition + 0.6969 69.69%
CYP inhibitory promiscuity - 0.8854 88.54%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7211 72.11%
Eye corrosion - 0.9866 98.66%
Eye irritation - 0.8971 89.71%
Skin irritation - 0.7319 73.19%
Skin corrosion - 0.9428 94.28%
Ames mutagenesis + 0.6046 60.46%
Human Ether-a-go-go-Related Gene inhibition + 0.7583 75.83%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5500 55.00%
skin sensitisation - 0.8580 85.80%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.4736 47.36%
Acute Oral Toxicity (c) III 0.5385 53.85%
Estrogen receptor binding + 0.7291 72.91%
Androgen receptor binding + 0.7395 73.95%
Thyroid receptor binding + 0.6661 66.61%
Glucocorticoid receptor binding + 0.7523 75.23%
Aromatase binding + 0.6007 60.07%
PPAR gamma + 0.7960 79.60%
Honey bee toxicity - 0.6820 68.20%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.8223 82.23%

Targets

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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 98.88% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.25% 96.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 95.19% 86.92%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 92.05% 91.24%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.59% 97.09%
CHEMBL4208 P20618 Proteasome component C5 87.97% 90.00%
CHEMBL5028 O14672 ADAM10 87.62% 97.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.62% 96.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.58% 95.83%
CHEMBL3401 O75469 Pregnane X receptor 85.27% 94.73%
CHEMBL226 P30542 Adenosine A1 receptor 84.43% 95.93%
CHEMBL2996 Q05655 Protein kinase C delta 83.21% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.70% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.57% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.47% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.97% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 80.78% 91.19%
CHEMBL5255 O00206 Toll-like receptor 4 80.47% 92.50%
CHEMBL4530 P00488 Coagulation factor XIII 80.17% 96.00%

Plants that contains it

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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 spinosa

Cross-Links

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PubChem 11557252
LOTUS LTS0068554
wikiData Q105127319