4-hydroxy-9-methyl-6-methylidene-3-(methylsulfonylmethyl)-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

Details

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Internal ID e1cdbfb9-6e89-4a97-8742-fb3617f5f1af
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name 4-hydroxy-9-methyl-6-methylidene-3-(methylsulfonylmethyl)-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
SMILES (Canonical) CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3CS(=O)(=O)C)O
SMILES (Isomeric) CC1C2C(CC1=O)C(=C)CC(C3C2OC(=O)C3CS(=O)(=O)C)O
InChI InChI=1S/C16H22O6S/c1-7-4-12(18)14-10(6-23(3,20)21)16(19)22-15(14)13-8(2)11(17)5-9(7)13/h8-10,12-15,18H,1,4-6H2,2-3H3
InChI Key WZRPLPASBYMJLL-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H22O6S
Molecular Weight 342.40 g/mol
Exact Mass 342.11370959 g/mol
Topological Polar Surface Area (TPSA) 106.00 Ų
XlogP -0.20
Atomic LogP (AlogP) 0.35
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-hydroxy-9-methyl-6-methylidene-3-(methylsulfonylmethyl)-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9562 95.62%
Caco-2 - 0.7007 70.07%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability + 0.6286 62.86%
Subcellular localzation Lysosomes 0.4706 47.06%
OATP2B1 inhibitior - 0.8572 85.72%
OATP1B1 inhibitior + 0.8465 84.65%
OATP1B3 inhibitior + 0.9387 93.87%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8067 80.67%
BSEP inhibitior - 0.8304 83.04%
P-glycoprotein inhibitior - 0.8018 80.18%
P-glycoprotein substrate - 0.7093 70.93%
CYP3A4 substrate + 0.5593 55.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8363 83.63%
CYP3A4 inhibition - 0.6099 60.99%
CYP2C9 inhibition - 0.7720 77.20%
CYP2C19 inhibition - 0.7290 72.90%
CYP2D6 inhibition - 0.8887 88.87%
CYP1A2 inhibition - 0.6494 64.94%
CYP2C8 inhibition - 0.9192 91.92%
CYP inhibitory promiscuity - 0.9644 96.44%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.5800 58.00%
Carcinogenicity (trinary) Non-required 0.6592 65.92%
Eye corrosion - 0.9637 96.37%
Eye irritation - 0.7611 76.11%
Skin irritation - 0.7453 74.53%
Skin corrosion - 0.8973 89.73%
Ames mutagenesis - 0.6554 65.54%
Human Ether-a-go-go-Related Gene inhibition - 0.7518 75.18%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.7587 75.87%
skin sensitisation - 0.8094 80.94%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.5707 57.07%
Acute Oral Toxicity (c) III 0.5363 53.63%
Estrogen receptor binding + 0.5432 54.32%
Androgen receptor binding + 0.5532 55.32%
Thyroid receptor binding - 0.5856 58.56%
Glucocorticoid receptor binding - 0.5469 54.69%
Aromatase binding - 0.8151 81.51%
PPAR gamma - 0.7576 75.76%
Honey bee toxicity - 0.7698 76.98%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6750 67.50%
Fish aquatic toxicity + 0.9916 99.16%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.31% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.68% 85.14%
CHEMBL2581 P07339 Cathepsin D 92.10% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.22% 86.92%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.06% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.66% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.44% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.63% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.35% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.24% 95.89%

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.
Cynara cardunculus

Cross-Links

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PubChem 163076327
LOTUS LTS0227230
wikiData Q105323424