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Gentiabavaroside

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 84fc0f4c-38dc-4fb0-a5f1-f293b65da5dc
Taxonomy Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
IUPAC Name 2-hydroxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
SMILES (Canonical) COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O)C(=O)C5=C(O2)C=CC(=C5OC)O
SMILES (Isomeric) COC1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)O)O)O)C(=O)C5=C(O2)C=CC(=C5OC)O
InChI InChI=1S/C26H30O15/c1-35-9-5-13-16(20(31)17-12(39-13)4-3-10(27)24(17)36-2)14(6-9)40-26-23(34)21(32)19(30)15(41-26)8-38-25-22(33)18(29)11(28)7-37-25/h3-6,11,15,18-19,21-23,25-30,32-34H,7-8H2,1-2H3/t11-,15-,18+,19-,21+,22-,23-,25+,26-/m1/s1
InChI Key UKMQUWHBRDHCSO-PVSYHSAYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C26H30O15
Molecular Weight 582.50 g/mol
Exact Mass 582.15847025 g/mol
Topological Polar Surface Area (TPSA) 223.00 Ų
XlogP -1.70
Atomic LogP (AlogP) -1.69
H-Bond Acceptor 15
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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2-hydroxy-1,6-dimethoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxymethyl)oxan-2-yl)oxyxanthen-9-one
2-hydroxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
RefChem:142898
CHEMBL501591

2D Structure

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2D Structure of Gentiabavaroside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5181 51.81%
Caco-2 - 0.8886 88.86%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.5700 57.00%
OATP2B1 inhibitior - 0.8526 85.26%
OATP1B1 inhibitior + 0.8931 89.31%
OATP1B3 inhibitior + 0.9535 95.35%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.7048 70.48%
P-glycoprotein inhibitior - 0.6176 61.76%
P-glycoprotein substrate - 0.6150 61.50%
CYP3A4 substrate + 0.6317 63.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8277 82.77%
CYP3A4 inhibition - 0.9082 90.82%
CYP2C9 inhibition - 0.9593 95.93%
CYP2C19 inhibition - 0.9192 91.92%
CYP2D6 inhibition - 0.8843 88.43%
CYP1A2 inhibition - 0.8533 85.33%
CYP2C8 inhibition + 0.4949 49.49%
CYP inhibitory promiscuity - 0.9119 91.19%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7055 70.55%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9276 92.76%
Skin irritation - 0.8390 83.90%
Skin corrosion - 0.9633 96.33%
Ames mutagenesis + 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3877 38.77%
Micronuclear + 0.5574 55.74%
Hepatotoxicity - 0.7351 73.51%
skin sensitisation - 0.8974 89.74%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.9577 95.77%
Acute Oral Toxicity (c) III 0.7230 72.30%
Estrogen receptor binding + 0.8227 82.27%
Androgen receptor binding + 0.5597 55.97%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.6078 60.78%
Aromatase binding + 0.6615 66.15%
PPAR gamma + 0.7540 75.40%
Honey bee toxicity - 0.8162 81.62%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.8120 81.20%

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 99.72% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 96.09% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.52% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.82% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 93.33% 99.15%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.43% 89.00%
CHEMBL2581 P07339 Cathepsin D 92.41% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.30% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.63% 94.45%
CHEMBL4208 P20618 Proteasome component C5 88.81% 90.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.85% 89.62%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.58% 95.83%
CHEMBL2535 P11166 Glucose transporter 85.46% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.00% 86.33%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.35% 93.99%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.83% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 83.61% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.46% 99.23%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.39% 92.62%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.97% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.81% 96.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.26% 85.14%

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.
Gentiana acaulis
Gentianopsis paludosa

Cross-Links

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PubChem 44577325
LOTUS LTS0026191
wikiData Q105274693