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(3aR,4R,6aR,9aR,9bR)-4-[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]-9-methyl-3,6-dimethylidene-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

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 94c7a538-3ed8-44d4-be81-a70913be1bb1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name (3aR,4R,6aR,9aR,9bR)-4-[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]-9-methyl-3,6-dimethylidene-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
SMILES (Canonical) CC1=C(CC2C1C3C(C(CC2=C)C(=O)C(CC4=CC=C(C=C4)O)O)C(=C)C(=O)O3)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)C(=O)C(CC4=CC=C(C=C4)O)O)C(=C)C(=O)O3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
InChI InChI=1S/C30H36O11/c1-12-8-18(24(34)19(33)9-15-4-6-16(32)7-5-15)23-14(3)29(38)41-28(23)22-13(2)20(10-17(12)22)39-30-27(37)26(36)25(35)21(11-31)40-30/h4-7,17-19,21-23,25-28,30-33,35-37H,1,3,8-11H2,2H3/t17-,18+,19?,21+,22-,23-,25+,26-,27+,28+,30+/m0/s1
InChI Key LMWIKUCPBZBCGD-WUBNGJEPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H36O11
Molecular Weight 572.60 g/mol
Exact Mass 572.22576196 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP 0.30
Atomic LogP (AlogP) 0.27
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3aR,4R,6aR,9aR,9bR)-4-[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]-9-methyl-3,6-dimethylidene-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8504 85.04%
Caco-2 - 0.8735 87.35%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6902 69.02%
OATP2B1 inhibitior - 0.8611 86.11%
OATP1B1 inhibitior + 0.8272 82.72%
OATP1B3 inhibitior + 0.9588 95.88%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.5807 58.07%
P-glycoprotein inhibitior - 0.5222 52.22%
P-glycoprotein substrate - 0.5230 52.30%
CYP3A4 substrate + 0.6898 68.98%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8784 87.84%
CYP3A4 inhibition - 0.6342 63.42%
CYP2C9 inhibition - 0.8443 84.43%
CYP2C19 inhibition - 0.7818 78.18%
CYP2D6 inhibition - 0.8929 89.29%
CYP1A2 inhibition - 0.7875 78.75%
CYP2C8 inhibition + 0.6299 62.99%
CYP inhibitory promiscuity - 0.8361 83.61%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6673 66.73%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9233 92.33%
Skin irritation - 0.7159 71.59%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis - 0.6354 63.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7383 73.83%
Micronuclear - 0.6500 65.00%
Hepatotoxicity - 0.7623 76.23%
skin sensitisation - 0.8215 82.15%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.6135 61.35%
Acute Oral Toxicity (c) III 0.4260 42.60%
Estrogen receptor binding + 0.7802 78.02%
Androgen receptor binding + 0.6910 69.10%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.5641 56.41%
Aromatase binding + 0.5714 57.14%
PPAR gamma + 0.6402 64.02%
Honey bee toxicity - 0.7001 70.01%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6850 68.50%
Fish aquatic toxicity + 0.9923 99.23%

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
CHEMBL2581 P07339 Cathepsin D 98.64% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.67% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.09% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.69% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.59% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.93% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.44% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.29% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.33% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.99% 95.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.66% 95.89%
CHEMBL3401 O75469 Pregnane X receptor 87.33% 94.73%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 84.05% 96.37%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.74% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.59% 94.00%
CHEMBL2996 Q05655 Protein kinase C delta 81.78% 97.79%
CHEMBL2535 P11166 Glucose transporter 80.74% 98.75%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.64% 97.36%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.54% 86.33%

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.
Lapsana communis

Cross-Links

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PubChem 101034737
LOTUS LTS0252109
wikiData Q105154164