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methyl (1S,4aR,6S,7R,7aS)-6-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[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 d43b6325-f68b-4094-9461-e2c53cd65678
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aR,6S,7R,7aS)-6-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1(C(CC2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)OC)OC)O
SMILES (Isomeric) C[C@@]1([C@H](C[C@]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)O)OC(=O)/C=C/C4=CC(=C(C=C4)OC)OC)O
InChI InChI=1S/C28H36O15/c1-27(35)18(42-19(30)8-6-13-5-7-15(37-2)16(9-13)38-3)10-28(36)14(24(34)39-4)12-40-26(23(27)28)43-25-22(33)21(32)20(31)17(11-29)41-25/h5-9,12,17-18,20-23,25-26,29,31-33,35-36H,10-11H2,1-4H3/b8-6+/t17-,18+,20-,21+,22-,23-,25+,26+,27+,28+/m1/s1
InChI Key FQNAUMYJWYEZSE-WZSBKURHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O15
Molecular Weight 612.60 g/mol
Exact Mass 612.20542044 g/mol
Topological Polar Surface Area (TPSA) 220.00 Ų
XlogP -0.50
Atomic LogP (AlogP) -1.64
H-Bond Acceptor 15
H-Bond Donor 6
Rotatable Bonds 9

Synonyms

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ACon1_001185
NCGC00169596-01
BRD-K46164908-001-01-6

2D Structure

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2D Structure of methyl (1S,4aR,6S,7R,7aS)-6-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[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 + 0.8454 84.54%
Caco-2 - 0.8739 87.39%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.4658 46.58%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior + 0.8458 84.58%
OATP1B3 inhibitior + 0.9271 92.71%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.4604 46.04%
P-glycoprotein inhibitior + 0.6184 61.84%
P-glycoprotein substrate + 0.5373 53.73%
CYP3A4 substrate + 0.6923 69.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8725 87.25%
CYP3A4 inhibition - 0.8810 88.10%
CYP2C9 inhibition - 0.8487 84.87%
CYP2C19 inhibition - 0.8786 87.86%
CYP2D6 inhibition - 0.9044 90.44%
CYP1A2 inhibition - 0.7251 72.51%
CYP2C8 inhibition + 0.7227 72.27%
CYP inhibitory promiscuity - 0.8573 85.73%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6674 66.74%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9295 92.95%
Skin irritation - 0.7165 71.65%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7252 72.52%
Micronuclear - 0.5600 56.00%
Hepatotoxicity - 0.7137 71.37%
skin sensitisation - 0.8386 83.86%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.8806 88.06%
Acute Oral Toxicity (c) III 0.3878 38.78%
Estrogen receptor binding + 0.8034 80.34%
Androgen receptor binding + 0.6723 67.23%
Thyroid receptor binding + 0.6037 60.37%
Glucocorticoid receptor binding + 0.7193 71.93%
Aromatase binding + 0.5826 58.26%
PPAR gamma + 0.7195 71.95%
Honey bee toxicity - 0.7593 75.93%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9007 90.07%

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 99.21% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.39% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.67% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.48% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.93% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.88% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.87% 95.89%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.34% 97.28%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.06% 92.94%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.82% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.17% 99.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.66% 95.50%
CHEMBL4208 P20618 Proteasome component C5 84.82% 90.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.68% 97.14%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.89% 89.50%
CHEMBL3401 O75469 Pregnane X receptor 83.15% 94.73%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.75% 91.07%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.30% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.93% 85.14%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.68% 95.83%

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.
Duranta erecta

Cross-Links

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PubChem 23844064
LOTUS LTS0148917
wikiData Q104999729