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(1S,4aR,6R,7R,7aS)-6-[(E)-3-[3-methoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]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-carboxylic acid

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 319b27b3-c8b7-4e15-bfca-310f9c75c9cc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aR,6R,7R,7aS)-6-[(E)-3-[3-methoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]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-carboxylic acid
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)O)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)OC
SMILES (Isomeric) C[C@H]1[C@@H](C[C@@H]2[C@@H]1[C@@H](OC=C2C(=O)O)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)OC
InChI InChI=1S/C32H42O18/c1-12-17(8-14-15(29(42)43)11-45-30(22(12)14)50-32-28(41)26(39)24(37)20(10-34)49-32)46-21(35)6-4-13-3-5-16(18(7-13)44-2)47-31-27(40)25(38)23(36)19(9-33)48-31/h3-7,11-12,14,17,19-20,22-28,30-34,36-41H,8-10H2,1-2H3,(H,42,43)/b6-4+/t12-,14-,17+,19+,20+,22+,23+,24+,25-,26-,27+,28+,30-,31-,32-/m0/s1
InChI Key QTZXVESWHBGRDB-MGHIWKHDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C32H42O18
Molecular Weight 714.70 g/mol
Exact Mass 714.23711449 g/mol
Topological Polar Surface Area (TPSA) 281.00 Ų
XlogP -1.20
Atomic LogP (AlogP) -2.79
H-Bond Acceptor 17
H-Bond Donor 9
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aR,6R,7R,7aS)-6-[(E)-3-[3-methoxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]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-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6928 69.28%
Caco-2 - 0.8894 88.94%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5463 54.63%
OATP2B1 inhibitior - 0.8618 86.18%
OATP1B1 inhibitior + 0.6945 69.45%
OATP1B3 inhibitior + 0.9574 95.74%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7019 70.19%
P-glycoprotein inhibitior + 0.5955 59.55%
P-glycoprotein substrate - 0.5374 53.74%
CYP3A4 substrate + 0.6606 66.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8725 87.25%
CYP3A4 inhibition - 0.8947 89.47%
CYP2C9 inhibition - 0.7896 78.96%
CYP2C19 inhibition - 0.7442 74.42%
CYP2D6 inhibition - 0.8884 88.84%
CYP1A2 inhibition - 0.7821 78.21%
CYP2C8 inhibition + 0.7555 75.55%
CYP inhibitory promiscuity - 0.6882 68.82%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7193 71.93%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9177 91.77%
Skin irritation - 0.7888 78.88%
Skin corrosion - 0.9434 94.34%
Ames mutagenesis - 0.5423 54.23%
Human Ether-a-go-go-Related Gene inhibition + 0.7759 77.59%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.7339 73.39%
skin sensitisation - 0.8200 82.00%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.9297 92.97%
Acute Oral Toxicity (c) III 0.5059 50.59%
Estrogen receptor binding + 0.8239 82.39%
Androgen receptor binding + 0.5521 55.21%
Thyroid receptor binding + 0.5132 51.32%
Glucocorticoid receptor binding + 0.6518 65.18%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.7034 70.34%
Honey bee toxicity - 0.7773 77.73%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9163 91.63%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.19% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.43% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.07% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.27% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.07% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.92% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.57% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.40% 99.17%
CHEMBL4208 P20618 Proteasome component C5 89.62% 90.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.40% 86.92%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.40% 89.62%
CHEMBL3194 P02766 Transthyretin 83.34% 90.71%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.22% 97.33%
CHEMBL5255 O00206 Toll-like receptor 4 82.04% 92.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.40% 95.50%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.29% 93.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.12% 96.95%
CHEMBL221 P23219 Cyclooxygenase-1 80.76% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.29% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 80.28% 94.73%

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.
Lonicera caerulea

Cross-Links

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PubChem 163016918
LOTUS LTS0000919
wikiData Q105228014