(2R)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-5-carboxy-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]ethenyl]pyridin-1-ium-1-yl]-3-phenylpropanoate

Details

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Internal ID 76df22d0-5eaf-4e94-a076-cf2d1044fd70
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name (2R)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-5-carboxy-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]ethenyl]pyridin-1-ium-1-yl]-3-phenylpropanoate
SMILES (Canonical) C=CC1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)O)C=CC3=CC(=C[N+](=C3)C(CC4=CC=CC=C4)C(=O)[O-])C(=O)O
SMILES (Isomeric) C=C[C@@H]1[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)O)/C=C/C3=CC(=C[N+](=C3)[C@H](CC4=CC=CC=C4)C(=O)[O-])C(=O)O
InChI InChI=1S/C31H33NO13/c1-2-19-20(21(28(39)40)15-43-30(19)45-31-26(36)25(35)24(34)23(14-33)44-31)9-8-17-10-18(27(37)38)13-32(12-17)22(29(41)42)11-16-6-4-3-5-7-16/h2-10,12-13,15,19-20,22-26,30-31,33-36H,1,11,14H2,(H2-,37,38,39,40,41,42)/b9-8+/t19-,20+,22-,23-,24-,25+,26-,30+,31+/m1/s1
InChI Key TYCHKAUZEONICT-LADCKBOFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H33NO13
Molecular Weight 627.60 g/mol
Exact Mass 627.19519011 g/mol
Topological Polar Surface Area (TPSA) 227.00 Ų
XlogP 1.80
Atomic LogP (AlogP) -1.22
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 12

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-5-carboxy-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]ethenyl]pyridin-1-ium-1-yl]-3-phenylpropanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.9258 92.58%
Caco-2 - 0.9060 90.60%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Nucleus 0.4176 41.76%
OATP2B1 inhibitior - 0.7055 70.55%
OATP1B1 inhibitior + 0.7828 78.28%
OATP1B3 inhibitior + 0.9376 93.76%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.8494 84.94%
P-glycoprotein inhibitior + 0.5920 59.20%
P-glycoprotein substrate - 0.5465 54.65%
CYP3A4 substrate + 0.6660 66.60%
CYP2C9 substrate - 0.8019 80.19%
CYP2D6 substrate - 0.8682 86.82%
CYP3A4 inhibition - 0.9666 96.66%
CYP2C9 inhibition - 0.7783 77.83%
CYP2C19 inhibition - 0.8151 81.51%
CYP2D6 inhibition - 0.8877 88.77%
CYP1A2 inhibition - 0.7596 75.96%
CYP2C8 inhibition + 0.7834 78.34%
CYP inhibitory promiscuity - 0.9111 91.11%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5402 54.02%
Eye corrosion - 0.9862 98.62%
Eye irritation - 0.9170 91.70%
Skin irritation - 0.7849 78.49%
Skin corrosion - 0.9378 93.78%
Ames mutagenesis + 0.5177 51.77%
Human Ether-a-go-go-Related Gene inhibition - 0.4219 42.19%
Micronuclear + 0.8200 82.00%
Hepatotoxicity - 0.6375 63.75%
skin sensitisation - 0.8570 85.70%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.6531 65.31%
Acute Oral Toxicity (c) III 0.5653 56.53%
Estrogen receptor binding + 0.7470 74.70%
Androgen receptor binding + 0.7100 71.00%
Thyroid receptor binding + 0.5752 57.52%
Glucocorticoid receptor binding + 0.6012 60.12%
Aromatase binding - 0.4899 48.99%
PPAR gamma + 0.7237 72.37%
Honey bee toxicity - 0.6288 62.88%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.7081 70.81%

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
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.04% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.80% 95.56%
CHEMBL2581 P07339 Cathepsin D 93.55% 98.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 92.50% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.26% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.37% 96.09%
CHEMBL220 P22303 Acetylcholinesterase 87.57% 94.45%
CHEMBL1741221 Q9Y4P1 Cysteine protease ATG4B 87.55% 87.50%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 86.76% 94.62%
CHEMBL3401 O75469 Pregnane X receptor 86.74% 94.73%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.17% 95.89%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 85.57% 91.71%
CHEMBL1255126 O15151 Protein Mdm4 84.60% 90.20%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 84.55% 89.67%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.88% 89.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 83.66% 91.11%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 82.78% 94.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.10% 95.89%
CHEMBL5678 P34947 G protein-coupled receptor kinase 5 81.05% 88.00%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 80.36% 83.57%

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.
Acacia aulacocarpa
Anemonastrum flaccidum
Ardisia neriifolia
Aspidosperma subincanum
Cryptocarya aschersoniana
Eupatorium argentinum
Garcinia madruno
Guatteria ucayalina
Juniperus brevifolia
Lonicera japonica
Peritassa compta
Psiadia dentata

Cross-Links

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PubChem 76324558
NPASS NPC111732
ChEMBL CHEMBL3092670