4-hydroxy-6-methyl-3-methylidene-9-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

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Internal ID d9c1d3d5-7663-4d9d-825d-7e30da2131c6
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name 4-hydroxy-6-methyl-3-methylidene-9-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
SMILES (Canonical) CC1=C2C(C3C(C(C1)O)C(=C)C(=O)O3)C(=CC2=O)COC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) CC1=C2C(C3C(C(C1)O)C(=C)C(=O)O3)C(=CC2=O)COC4C(C(C(C(O4)CO)O)O)O
InChI InChI=1S/C21H26O10/c1-7-3-10(23)14-8(2)20(28)31-19(14)15-9(4-11(24)13(7)15)6-29-21-18(27)17(26)16(25)12(5-22)30-21/h4,10,12,14-19,21-23,25-27H,2-3,5-6H2,1H3
InChI Key NCNUKSMLRPTJBC-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H26O10
Molecular Weight 438.40 g/mol
Exact Mass 438.15259702 g/mol
Topological Polar Surface Area (TPSA) 163.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -1.89
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-hydroxy-6-methyl-3-methylidene-9-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6405 64.05%
Caco-2 - 0.8384 83.84%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6621 66.21%
OATP2B1 inhibitior - 0.8607 86.07%
OATP1B1 inhibitior + 0.8677 86.77%
OATP1B3 inhibitior + 0.9520 95.20%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.5821 58.21%
P-glycoprotein inhibitior - 0.7492 74.92%
P-glycoprotein substrate - 0.7348 73.48%
CYP3A4 substrate + 0.6212 62.12%
CYP2C9 substrate - 0.8034 80.34%
CYP2D6 substrate - 0.8981 89.81%
CYP3A4 inhibition - 0.8951 89.51%
CYP2C9 inhibition - 0.8653 86.53%
CYP2C19 inhibition - 0.8334 83.34%
CYP2D6 inhibition - 0.9130 91.30%
CYP1A2 inhibition - 0.8621 86.21%
CYP2C8 inhibition - 0.6775 67.75%
CYP inhibitory promiscuity - 0.9287 92.87%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6605 66.05%
Eye corrosion - 0.9832 98.32%
Eye irritation - 0.9417 94.17%
Skin irritation - 0.7446 74.46%
Skin corrosion - 0.9308 93.08%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4014 40.14%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.5129 51.29%
skin sensitisation - 0.8530 85.30%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.7820 78.20%
Acute Oral Toxicity (c) III 0.5094 50.94%
Estrogen receptor binding + 0.6814 68.14%
Androgen receptor binding + 0.6713 67.13%
Thyroid receptor binding - 0.6012 60.12%
Glucocorticoid receptor binding + 0.6065 60.65%
Aromatase binding + 0.5359 53.59%
PPAR gamma + 0.5275 52.75%
Honey bee toxicity - 0.7423 74.23%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6250 62.50%
Fish aquatic toxicity + 0.8088 80.88%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.55% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.62% 91.11%
CHEMBL2581 P07339 Cathepsin D 91.73% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 90.86% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.25% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.07% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.95% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.02% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 86.11% 97.36%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.72% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.67% 96.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.58% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.68% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.85% 89.00%

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.
Lactuca virosa
Picris hieracioides

Cross-Links

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PubChem 73817429
LOTUS LTS0250431
wikiData Q105177293