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[(3aR,4S,9aS,9bR)-6-methyl-3-methylidene-2,7-dioxo-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

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 c8023e09-67c6-45f0-9a6f-8385ab9ed429
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name [(3aR,4S,9aS,9bR)-6-methyl-3-methylidene-2,7-dioxo-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate
SMILES (Canonical) CC1=C2C(C3C(C(C1)OC(=O)C(=C)C4CCC(=C5C(C4)C(=CC5=O)C)CO)C(=C)C(=O)O3)C(=CC2=O)COC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)OC(=O)C(=C)[C@@H]4CCC(=C5[C@@H](C4)C(=CC5=O)C)CO)C(=C)C(=O)O3)C(=CC2=O)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C36H42O13/c1-14-7-22(39)28-19(11-37)6-5-18(9-21(14)28)16(3)34(44)47-24-8-15(2)26-23(40)10-20(29(26)33-27(24)17(4)35(45)49-33)13-46-36-32(43)31(42)30(41)25(12-38)48-36/h7,10,18,21,24-25,27,29-33,36-38,41-43H,3-6,8-9,11-13H2,1-2H3/t18-,21+,24+,25-,27-,29+,30-,31+,32-,33+,36-/m1/s1
InChI Key HCKRLHVPHIPBKX-WXYLEYPZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C36H42O13
Molecular Weight 682.70 g/mol
Exact Mass 682.26254139 g/mol
Topological Polar Surface Area (TPSA) 206.00 Ų
XlogP -0.70
Atomic LogP (AlogP) 0.45
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,9aS,9bR)-6-methyl-3-methylidene-2,7-dioxo-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-[(3aS,5R)-8-(hydroxymethyl)-3-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7126 71.26%
Caco-2 - 0.8638 86.38%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8249 82.49%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8396 83.96%
OATP1B3 inhibitior + 0.9322 93.22%
MATE1 inhibitior - 0.9012 90.12%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.6300 63.00%
P-glycoprotein inhibitior + 0.7105 71.05%
P-glycoprotein substrate + 0.6462 64.62%
CYP3A4 substrate + 0.7115 71.15%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8986 89.86%
CYP3A4 inhibition - 0.8919 89.19%
CYP2C9 inhibition - 0.8587 85.87%
CYP2C19 inhibition - 0.8429 84.29%
CYP2D6 inhibition - 0.9123 91.23%
CYP1A2 inhibition - 0.7519 75.19%
CYP2C8 inhibition + 0.7493 74.93%
CYP inhibitory promiscuity - 0.9359 93.59%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6937 69.37%
Eye corrosion - 0.9829 98.29%
Eye irritation - 0.9123 91.23%
Skin irritation - 0.6914 69.14%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis - 0.7154 71.54%
Human Ether-a-go-go-Related Gene inhibition + 0.6925 69.25%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.5623 56.23%
skin sensitisation - 0.8866 88.66%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.6825 68.25%
Acute Oral Toxicity (c) III 0.4821 48.21%
Estrogen receptor binding + 0.8093 80.93%
Androgen receptor binding + 0.7539 75.39%
Thyroid receptor binding - 0.5487 54.87%
Glucocorticoid receptor binding + 0.6304 63.04%
Aromatase binding + 0.6112 61.12%
PPAR gamma + 0.7124 71.24%
Honey bee toxicity - 0.6769 67.69%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9766 97.66%

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 95.89% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.00% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.31% 91.11%
CHEMBL2581 P07339 Cathepsin D 92.58% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.80% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 90.36% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.17% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.61% 96.09%
CHEMBL4072 P07858 Cathepsin B 88.82% 93.67%
CHEMBL226 P30542 Adenosine A1 receptor 86.83% 95.93%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.55% 97.25%
CHEMBL3714130 P46095 G-protein coupled receptor 6 86.29% 97.36%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.67% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.37% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.84% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.49% 99.23%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.71% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.16% 94.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.11% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.79% 95.50%

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.
Picris hieracioides

Cross-Links

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PubChem 14781494
LOTUS LTS0032102
wikiData Q105025793