(2R,3R,4R,5R,6S)-2-[[(1R,4aR,5S,6R,8aS)-6-hydroxy-1,4a,6-trimethyl-5-[(3S)-3-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypent-4-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

Top
Internal ID e068e509-6dc4-469d-a5c9-0e7e1fcedac8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
IUPAC Name (2R,3R,4R,5R,6S)-2-[[(1R,4aR,5S,6R,8aS)-6-hydroxy-1,4a,6-trimethyl-5-[(3S)-3-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypent-4-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OCC2(CCCC3(C2CCC(C3CCC(C)(C=C)OC4C(C(C(C(O4)C)O)O)O)(C)O)C)C)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@]2(CCC[C@@]3([C@@H]2CC[C@@]([C@H]3CC[C@@](C)(C=C)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)(C)O)C)C)O)O)O
InChI InChI=1S/C32H56O11/c1-8-30(5,43-28-26(38)24(36)22(34)18(3)42-28)14-10-20-31(6)13-9-12-29(4,19(31)11-15-32(20,7)39)16-40-27-25(37)23(35)21(33)17(2)41-27/h8,17-28,33-39H,1,9-16H2,2-7H3/t17-,18-,19+,20-,21-,22-,23+,24+,25+,26+,27+,28-,29-,30+,31+,32+/m0/s1
InChI Key WLTDCOMQNJRVOZ-ISYNVZIYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C32H56O11
Molecular Weight 616.80 g/mol
Exact Mass 616.38226260 g/mol
Topological Polar Surface Area (TPSA) 179.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.37
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (2R,3R,4R,5R,6S)-2-[[(1R,4aR,5S,6R,8aS)-6-hydroxy-1,4a,6-trimethyl-5-[(3S)-3-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypent-4-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]-6-methyloxane-3,4,5-triol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5731 57.31%
Caco-2 - 0.8319 83.19%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.6554 65.54%
OATP2B1 inhibitior - 0.7209 72.09%
OATP1B1 inhibitior + 0.8516 85.16%
OATP1B3 inhibitior + 0.8436 84.36%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior - 0.8066 80.66%
P-glycoprotein inhibitior + 0.6637 66.37%
P-glycoprotein substrate - 0.6510 65.10%
CYP3A4 substrate + 0.6809 68.09%
CYP2C9 substrate - 0.7878 78.78%
CYP2D6 substrate - 0.8346 83.46%
CYP3A4 inhibition - 0.8774 87.74%
CYP2C9 inhibition - 0.9131 91.31%
CYP2C19 inhibition - 0.8678 86.78%
CYP2D6 inhibition - 0.9593 95.93%
CYP1A2 inhibition - 0.8791 87.91%
CYP2C8 inhibition + 0.6668 66.68%
CYP inhibitory promiscuity - 0.9641 96.41%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7084 70.84%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9220 92.20%
Skin irritation - 0.5874 58.74%
Skin corrosion - 0.9460 94.60%
Ames mutagenesis - 0.6854 68.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7241 72.41%
Micronuclear - 0.9000 90.00%
Hepatotoxicity - 0.6723 67.23%
skin sensitisation - 0.9072 90.72%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.8829 88.29%
Acute Oral Toxicity (c) III 0.3975 39.75%
Estrogen receptor binding + 0.6210 62.10%
Androgen receptor binding + 0.5928 59.28%
Thyroid receptor binding - 0.5389 53.89%
Glucocorticoid receptor binding + 0.5571 55.71%
Aromatase binding + 0.6561 65.61%
PPAR gamma + 0.6104 61.04%
Honey bee toxicity - 0.7468 74.68%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9604 96.04%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.19% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.39% 91.11%
CHEMBL325 Q13547 Histone deacetylase 1 95.65% 95.92%
CHEMBL1951 P21397 Monoamine oxidase A 94.25% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.62% 96.09%
CHEMBL206 P03372 Estrogen receptor alpha 92.92% 97.64%
CHEMBL218 P21554 Cannabinoid CB1 receptor 92.80% 96.61%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.28% 92.94%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.88% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.29% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 91.14% 95.93%
CHEMBL1937 Q92769 Histone deacetylase 2 90.24% 94.75%
CHEMBL2581 P07339 Cathepsin D 88.62% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.89% 86.33%
CHEMBL259 P32245 Melanocortin receptor 4 87.47% 95.38%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.20% 89.00%
CHEMBL233 P35372 Mu opioid receptor 84.77% 97.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.62% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 84.45% 95.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 84.09% 89.05%
CHEMBL2179 P04062 Beta-glucocerebrosidase 83.15% 85.31%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 83.10% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.96% 97.14%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.71% 91.07%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 82.31% 97.47%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 81.89% 91.03%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.68% 97.36%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.23% 92.62%

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.
Sticherus quadripartitus

Cross-Links

Top
PubChem 163086102
LOTUS LTS0229174
wikiData Q105308194