6'-O-vanillylpaeoniflorin

Details

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Internal ID 6e04337f-dea8-4b4c-85ad-8ac53da46e99
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name [(1R,2S,3S,5S,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(4-hydroxy-3-methoxyphenyl)methoxymethyl]oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
SMILES (Canonical) CC12CC3(C4CC1(C4(C(O2)O3)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)COCC7=CC(=C(C=C7)O)OC)O)O)O)O
SMILES (Isomeric) C[C@]12C[C@@]3([C@H]4C[C@@]1([C@@]4([C@H](O2)O3)COC(=O)C5=CC=CC=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COCC7=CC(=C(C=C7)O)OC)O)O)O)O
InChI InChI=1S/C31H36O13/c1-28-14-30(37)21-11-31(28,29(21,27(43-28)44-30)15-40-25(36)17-6-4-3-5-7-17)42-26-24(35)23(34)22(33)20(41-26)13-39-12-16-8-9-18(32)19(10-16)38-2/h3-10,20-24,26-27,32-35,37H,11-15H2,1-2H3/t20-,21+,22-,23+,24-,26+,27-,28+,29+,30-,31-/m1/s1
InChI Key TUUZZRKOUMSRMU-ZHNAOBHOSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C31H36O13
Molecular Weight 616.60 g/mol
Exact Mass 616.21559120 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP 0.10
Atomic LogP (AlogP) 0.58
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 10

Synonyms

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CHEMBL1077644

2D Structure

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2D Structure of 6'-O-vanillylpaeoniflorin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8342 83.42%
Caco-2 - 0.8593 85.93%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.5643 56.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8910 89.10%
OATP1B3 inhibitior + 0.9424 94.24%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.7104 71.04%
P-glycoprotein inhibitior + 0.6708 67.08%
P-glycoprotein substrate + 0.5162 51.62%
CYP3A4 substrate + 0.7188 71.88%
CYP2C9 substrate - 0.7992 79.92%
CYP2D6 substrate - 0.8421 84.21%
CYP3A4 inhibition - 0.7682 76.82%
CYP2C9 inhibition - 0.8867 88.67%
CYP2C19 inhibition - 0.8095 80.95%
CYP2D6 inhibition - 0.9106 91.06%
CYP1A2 inhibition - 0.8358 83.58%
CYP2C8 inhibition + 0.8502 85.02%
CYP inhibitory promiscuity - 0.9510 95.10%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5873 58.73%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.9222 92.22%
Skin irritation - 0.7753 77.53%
Skin corrosion - 0.9396 93.96%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6472 64.72%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.7594 75.94%
skin sensitisation - 0.8524 85.24%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.9469 94.69%
Acute Oral Toxicity (c) III 0.3755 37.55%
Estrogen receptor binding + 0.8442 84.42%
Androgen receptor binding + 0.7572 75.72%
Thyroid receptor binding + 0.5819 58.19%
Glucocorticoid receptor binding + 0.6806 68.06%
Aromatase binding + 0.7063 70.63%
PPAR gamma + 0.7110 71.10%
Honey bee toxicity - 0.7076 70.76%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9788 97.88%

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 99.14% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.19% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.02% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.76% 99.17%
CHEMBL2535 P11166 Glucose transporter 91.23% 98.75%
CHEMBL2179 P04062 Beta-glucocerebrosidase 89.73% 85.31%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 89.52% 95.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 89.00% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.88% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.87% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.83% 95.89%
CHEMBL2581 P07339 Cathepsin D 88.55% 98.95%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 87.39% 96.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 86.33% 96.61%
CHEMBL226 P30542 Adenosine A1 receptor 86.24% 95.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.90% 92.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.78% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.06% 97.14%
CHEMBL340 P08684 Cytochrome P450 3A4 84.06% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.29% 94.00%
CHEMBL221 P23219 Cyclooxygenase-1 82.01% 90.17%
CHEMBL3401 O75469 Pregnane X receptor 81.27% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.06% 89.00%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 80.74% 92.67%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.43% 94.08%

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.
Paeonia suffruticosa

Cross-Links

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PubChem 46882881
LOTUS LTS0136176
wikiData Q105265062