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Gardaloside

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 d9e453ae-94b3-4b05-a62d-c211cc022f57
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
SMILES (Canonical) C=C1C(CC2C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O
SMILES (Isomeric) C=C1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI InChI=1S/C16H22O9/c1-6-9(19)2-8-7(3-17)5-23-15(11(6)8)25-16-14(22)13(21)12(20)10(4-18)24-16/h3,5,8-16,18-22H,1-2,4H2/t8-,9+,10-,11-,12-,13+,14-,15+,16+/m1/s1
InChI Key KGDIDCUROGOWDM-WDALVHIASA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C16H22O9
Molecular Weight 358.34 g/mol
Exact Mass 358.12638228 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP -2.50
Atomic LogP (AlogP) -2.20
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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(1S,4aS,6S,7aS)-6-hydroxy-7-methylidene-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde

2D Structure

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2D Structure of Gardaloside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5803 58.03%
Caco-2 - 0.8615 86.15%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.5877 58.77%
OATP2B1 inhibitior - 0.8601 86.01%
OATP1B1 inhibitior + 0.7592 75.92%
OATP1B3 inhibitior + 0.9516 95.16%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9613 96.13%
P-glycoprotein inhibitior - 0.8693 86.93%
P-glycoprotein substrate - 0.8621 86.21%
CYP3A4 substrate + 0.5585 55.85%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8363 83.63%
CYP3A4 inhibition - 0.8439 84.39%
CYP2C9 inhibition - 0.9240 92.40%
CYP2C19 inhibition - 0.8599 85.99%
CYP2D6 inhibition - 0.8838 88.38%
CYP1A2 inhibition - 0.8890 88.90%
CYP2C8 inhibition - 0.7146 71.46%
CYP inhibitory promiscuity - 0.8568 85.68%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7487 74.87%
Eye corrosion - 0.9873 98.73%
Eye irritation - 0.9254 92.54%
Skin irritation - 0.7650 76.50%
Skin corrosion - 0.9472 94.72%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4120 41.20%
Micronuclear - 0.6841 68.41%
Hepatotoxicity - 0.7643 76.43%
skin sensitisation - 0.8465 84.65%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity + 0.6488 64.88%
Acute Oral Toxicity (c) III 0.4029 40.29%
Estrogen receptor binding + 0.5389 53.89%
Androgen receptor binding - 0.4817 48.17%
Thyroid receptor binding + 0.5722 57.22%
Glucocorticoid receptor binding - 0.5747 57.47%
Aromatase binding + 0.5881 58.81%
PPAR gamma + 0.5350 53.50%
Honey bee toxicity - 0.7209 72.09%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6555 65.55%
Fish aquatic toxicity + 0.6594 65.94%

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 96.29% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.79% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 89.94% 96.61%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.27% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.30% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 83.84% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.00% 89.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.81% 97.36%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.35% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.13% 86.92%

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.
Gardenia jasminoides

Cross-Links

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PubChem 11631807
NPASS NPC92661
LOTUS LTS0251635
wikiData Q105140696