[(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,7,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

Top
Internal ID 093e57ca-937b-44bb-a6fa-76e65ac27cf4
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name [(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,7,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
SMILES (Canonical) CC1=C2CC=C(C2C3C(C(C1)OC4C(C(C(C(O4)CO)O)O)O)C(=C)C(=O)O3)COC5C(C(C(C(O5)COC(=O)CC6=CC=C(C=C6)O)O)O)O
SMILES (Isomeric) CC1=C2CC=C([C@@H]2[C@@H]3[C@@H]([C@H](C1)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=C)C(=O)O3)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)CC6=CC=C(C=C6)O)O)O)O
InChI InChI=1S/C35H44O16/c1-14-9-20(48-35-31(44)28(41)26(39)21(11-36)49-35)24-15(2)33(45)51-32(24)25-17(5-8-19(14)25)12-47-34-30(43)29(42)27(40)22(50-34)13-46-23(38)10-16-3-6-18(37)7-4-16/h3-7,20-22,24-32,34-37,39-44H,2,8-13H2,1H3/t20-,21+,22+,24+,25-,26+,27+,28-,29-,30+,31+,32-,34+,35+/m0/s1
InChI Key NWAICQLPBNMFRL-CFLGGORVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C35H44O16
Molecular Weight 720.70 g/mol
Exact Mass 720.26293531 g/mol
Topological Polar Surface Area (TPSA) 251.00 Ų
XlogP -2.00
Atomic LogP (AlogP) -1.75
H-Bond Acceptor 16
H-Bond Donor 8
Rotatable Bonds 10

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(2R,3S,4S,5R,6R)-6-[[(3aR,4S,9aR,9bR)-6-methyl-3-methylidene-2-oxo-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,7,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8515 85.15%
Caco-2 - 0.8823 88.23%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7387 73.87%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8271 82.71%
OATP1B3 inhibitior + 0.9413 94.13%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8993 89.93%
P-glycoprotein inhibitior + 0.6640 66.40%
P-glycoprotein substrate + 0.5246 52.46%
CYP3A4 substrate + 0.7004 70.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8827 88.27%
CYP3A4 inhibition - 0.7550 75.50%
CYP2C9 inhibition - 0.8292 82.92%
CYP2C19 inhibition - 0.7133 71.33%
CYP2D6 inhibition - 0.8841 88.41%
CYP1A2 inhibition - 0.7766 77.66%
CYP2C8 inhibition + 0.7288 72.88%
CYP inhibitory promiscuity - 0.7821 78.21%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6342 63.42%
Eye corrosion - 0.9857 98.57%
Eye irritation - 0.9154 91.54%
Skin irritation - 0.7389 73.89%
Skin corrosion - 0.9376 93.76%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6997 69.97%
Micronuclear - 0.6500 65.00%
Hepatotoxicity - 0.6643 66.43%
skin sensitisation - 0.8285 82.85%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.6839 68.39%
Acute Oral Toxicity (c) III 0.4535 45.35%
Estrogen receptor binding + 0.8061 80.61%
Androgen receptor binding + 0.6860 68.60%
Thyroid receptor binding - 0.5198 51.98%
Glucocorticoid receptor binding + 0.6613 66.13%
Aromatase binding + 0.5814 58.14%
PPAR gamma + 0.7282 72.82%
Honey bee toxicity - 0.6848 68.48%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5950 59.50%
Fish aquatic toxicity + 0.9970 99.70%

Targets

Top

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.23% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.22% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 92.03% 94.73%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.75% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.69% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 91.25% 97.79%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.12% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.74% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.73% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.64% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.34% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.15% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.44% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.34% 99.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.55% 95.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.05% 95.89%
CHEMBL221 P23219 Cyclooxygenase-1 85.87% 90.17%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.81% 97.36%
CHEMBL220 P22303 Acetylcholinesterase 83.54% 94.45%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.27% 97.33%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 82.20% 90.93%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 81.38% 93.65%

Plants that contains it

Top
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.
Crepidiastrum lanceolatum

Cross-Links

Top
PubChem 102465586
LOTUS LTS0171151
wikiData Q105186500