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methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[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 c8250404-55d3-4494-925b-87405abb7973
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)C
SMILES (Isomeric) CC(=O)O[C@]1(C[C@H]([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)/C=C/C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C
InChI InChI=1S/C34H44O19/c1-14(37)53-34(2)10-18(22-17(30(45)46-3)13-47-31(23(22)34)52-33-29(44)27(42)25(40)20(12-36)51-33)49-21(38)9-6-15-4-7-16(8-5-15)48-32-28(43)26(41)24(39)19(11-35)50-32/h4-9,13,18-20,22-29,31-33,35-36,39-44H,10-12H2,1-3H3/b9-6+/t18-,19-,20-,22+,23-,24-,25-,26+,27+,28-,29-,31+,32-,33+,34+/m1/s1
InChI Key HHIBYENHLKOCEO-ATCKIDBWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H44O19
Molecular Weight 756.70 g/mol
Exact Mass 756.24767917 g/mol
Topological Polar Surface Area (TPSA) 287.00 Ų
XlogP -1.50
Atomic LogP (AlogP) -3.02
H-Bond Acceptor 19
H-Bond Donor 8
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[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 + 0.6395 63.95%
Caco-2 - 0.8791 87.91%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.6050 60.50%
OATP2B1 inhibitior - 0.7199 71.99%
OATP1B1 inhibitior + 0.8307 83.07%
OATP1B3 inhibitior + 0.9086 90.86%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.7927 79.27%
P-glycoprotein inhibitior + 0.6882 68.82%
P-glycoprotein substrate + 0.5228 52.28%
CYP3A4 substrate + 0.7092 70.92%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8814 88.14%
CYP3A4 inhibition - 0.8866 88.66%
CYP2C9 inhibition - 0.8156 81.56%
CYP2C19 inhibition - 0.8073 80.73%
CYP2D6 inhibition - 0.9309 93.09%
CYP1A2 inhibition - 0.8400 84.00%
CYP2C8 inhibition + 0.7293 72.93%
CYP inhibitory promiscuity - 0.7592 75.92%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5579 55.79%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9175 91.75%
Skin irritation - 0.7555 75.55%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.5537 55.37%
Human Ether-a-go-go-Related Gene inhibition + 0.8313 83.13%
Micronuclear - 0.5800 58.00%
Hepatotoxicity - 0.8370 83.70%
skin sensitisation - 0.8381 83.81%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.4242 42.42%
Estrogen receptor binding + 0.8087 80.87%
Androgen receptor binding + 0.6647 66.47%
Thyroid receptor binding + 0.5797 57.97%
Glucocorticoid receptor binding + 0.7126 71.26%
Aromatase binding + 0.5277 52.77%
PPAR gamma + 0.7610 76.10%
Honey bee toxicity - 0.6829 68.29%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6800 68.00%
Fish aquatic toxicity + 0.8978 89.78%

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 99.32% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.50% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 97.04% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.60% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.34% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.52% 97.09%
CHEMBL4208 P20618 Proteasome component C5 92.64% 90.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.11% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.33% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.66% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 88.33% 95.93%
CHEMBL3401 O75469 Pregnane X receptor 86.99% 94.73%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 85.19% 94.08%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.84% 99.17%
CHEMBL3922 P50579 Methionine aminopeptidase 2 84.31% 97.28%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.22% 95.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.54% 91.07%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.46% 96.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.54% 92.62%
CHEMBL5028 O14672 ADAM10 81.41% 97.50%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.25% 95.83%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.17% 94.33%

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.
Barleria lupulina

Cross-Links

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PubChem 102023656
LOTUS LTS0116677
wikiData Q105028300