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(3R,3aR,4S,6aR,9aR,9bR)-9-methyl-6-methylidene-2-oxo-4-[(3S)-piperidin-3-yl]oxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-3-carboxylic acid

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 26897f49-9d2d-4577-9939-f804f20a670c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3R,3aR,4S,6aR,9aR,9bR)-9-methyl-6-methylidene-2-oxo-4-[(3S)-piperidin-3-yl]oxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-3-carboxylic acid
SMILES (Canonical) CC1=C(CC2C1C3C(C(CC2=C)OC4CCCNC4)C(C(=O)O3)C(=O)O)OC5C(C(C(C(O5)CO)O)O)O
SMILES (Isomeric) CC1=C(C[C@@H]2[C@H]1[C@@H]3[C@@H]([C@H](CC2=C)O[C@H]4CCCNC4)[C@@H](C(=O)O3)C(=O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
InChI InChI=1S/C26H37NO11/c1-10-6-15(35-12-4-3-5-27-8-12)18-19(24(32)33)25(34)38-23(18)17-11(2)14(7-13(10)17)36-26-22(31)21(30)20(29)16(9-28)37-26/h12-13,15-23,26-31H,1,3-9H2,2H3,(H,32,33)/t12-,13-,15-,16+,17-,18-,19+,20+,21-,22+,23+,26+/m0/s1
InChI Key CNKIBFUYXUADJG-KBUDCCMOSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H37NO11
Molecular Weight 539.60 g/mol
Exact Mass 539.23666100 g/mol
Topological Polar Surface Area (TPSA) 184.00 Ų
XlogP -2.80
Atomic LogP (AlogP) -0.95
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,3aR,4S,6aR,9aR,9bR)-9-methyl-6-methylidene-2-oxo-4-[(3S)-piperidin-3-yl]oxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-3-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6298 62.98%
Caco-2 - 0.8659 86.59%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.5370 53.70%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8400 84.00%
OATP1B3 inhibitior + 0.9477 94.77%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.5914 59.14%
P-glycoprotein inhibitior - 0.5709 57.09%
P-glycoprotein substrate - 0.5277 52.77%
CYP3A4 substrate + 0.6925 69.25%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8660 86.60%
CYP3A4 inhibition - 0.9441 94.41%
CYP2C9 inhibition - 0.8793 87.93%
CYP2C19 inhibition - 0.8584 85.84%
CYP2D6 inhibition - 0.8916 89.16%
CYP1A2 inhibition - 0.8250 82.50%
CYP2C8 inhibition + 0.5164 51.64%
CYP inhibitory promiscuity - 0.9644 96.44%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6063 60.63%
Eye corrosion - 0.9846 98.46%
Eye irritation - 0.9272 92.72%
Skin irritation - 0.7131 71.31%
Skin corrosion - 0.9153 91.53%
Ames mutagenesis - 0.6624 66.24%
Human Ether-a-go-go-Related Gene inhibition - 0.4359 43.59%
Micronuclear - 0.5900 59.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.8362 83.62%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.6527 65.27%
Acute Oral Toxicity (c) III 0.5520 55.20%
Estrogen receptor binding + 0.6591 65.91%
Androgen receptor binding + 0.5697 56.97%
Thyroid receptor binding - 0.5514 55.14%
Glucocorticoid receptor binding - 0.5684 56.84%
Aromatase binding + 0.5484 54.84%
PPAR gamma + 0.5538 55.38%
Honey bee toxicity - 0.7731 77.31%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6350 63.50%
Fish aquatic toxicity + 0.7148 71.48%

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
CHEMBL3137262 O60341 LSD1/CoREST complex 98.63% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.99% 91.11%
CHEMBL220 P22303 Acetylcholinesterase 95.48% 94.45%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 93.86% 96.21%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.43% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.13% 98.95%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 90.50% 95.58%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.71% 85.14%
CHEMBL5255 O00206 Toll-like receptor 4 89.61% 92.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.04% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.77% 95.56%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 88.32% 91.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.30% 95.89%
CHEMBL228 P31645 Serotonin transporter 87.60% 95.51%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.14% 93.00%
CHEMBL5103 Q969S8 Histone deacetylase 10 87.11% 90.08%
CHEMBL4072 P07858 Cathepsin B 86.17% 93.67%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.54% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.01% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.80% 94.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.71% 96.47%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.03% 97.25%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.90% 94.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.53% 96.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.37% 96.61%

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.
Youngia japonica

Cross-Links

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PubChem 163187916
LOTUS LTS0030019
wikiData Q104965920