PlantaeDB Logo
Login Sign-up

(6S)-6-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-1-en-3-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

Top
Internal ID 4e15193c-b6bd-418a-8328-a2b56ceb01fc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (6S)-6-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-1-en-3-one
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C)(CCC(=O)C(=C)C)C3CCC4(C3C(CC5C4(CCC6C5(CC(C(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)O)C)C)O)C)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@](C)(CCC(=O)C(=C)C)[C@H]3CC[C@@]4([C@@H]3[C@@H](C[C@H]5[C@]4(CC[C@@H]6[C@@]5(C[C@H]([C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)C)C)O)C)O)O)O)O)O)O
InChI InChI=1S/C54H90O24/c1-21(2)24(57)11-15-54(9,78-48-43(70)39(66)36(63)29(75-48)20-71-46-41(68)37(64)33(60)22(3)72-46)23-10-13-53(8)32(23)25(58)16-31-51(6)17-26(59)45(50(4,5)30(51)12-14-52(31,53)7)77-49-44(40(67)35(62)28(19-56)74-49)76-47-42(69)38(65)34(61)27(18-55)73-47/h22-23,25-49,55-56,58-70H,1,10-20H2,2-9H3/t22-,23-,25+,26+,27+,28+,29+,30-,31+,32-,33-,34+,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-,46+,47-,48-,49-,51-,52+,53+,54-/m0/s1
InChI Key RKMLZLOLTFLUQX-OVZYVKQASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C54H90O24
Molecular Weight 1123.30 g/mol
Exact Mass 1122.58220373 g/mol
Topological Polar Surface Area (TPSA) 394.00 Ų
XlogP -1.50
Atomic LogP (AlogP) -3.03
H-Bond Acceptor 24
H-Bond Donor 15
Rotatable Bonds 16

Synonyms

Top
BDBM50090475

2D Structure

Top
2D Structure of (6S)-6-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,12-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-1-en-3-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7532 75.32%
Caco-2 - 0.8935 89.35%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7797 77.97%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8243 82.43%
OATP1B3 inhibitior - 0.2425 24.25%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.7276 72.76%
BSEP inhibitior + 0.9049 90.49%
P-glycoprotein inhibitior + 0.7482 74.82%
P-glycoprotein substrate + 0.5766 57.66%
CYP3A4 substrate + 0.7352 73.52%
CYP2C9 substrate - 0.8008 80.08%
CYP2D6 substrate - 0.8723 87.23%
CYP3A4 inhibition - 0.9192 91.92%
CYP2C9 inhibition - 0.8356 83.56%
CYP2C19 inhibition - 0.8825 88.25%
CYP2D6 inhibition - 0.9389 93.89%
CYP1A2 inhibition - 0.8922 89.22%
CYP2C8 inhibition + 0.7217 72.17%
CYP inhibitory promiscuity - 0.9530 95.30%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6708 67.08%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9002 90.02%
Skin irritation - 0.5254 52.54%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.7554 75.54%
Human Ether-a-go-go-Related Gene inhibition + 0.8102 81.02%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.5209 52.09%
skin sensitisation - 0.8880 88.80%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.5500 55.00%
Nephrotoxicity - 0.6141 61.41%
Acute Oral Toxicity (c) III 0.4753 47.53%
Estrogen receptor binding + 0.7876 78.76%
Androgen receptor binding + 0.7523 75.23%
Thyroid receptor binding + 0.5462 54.62%
Glucocorticoid receptor binding + 0.7710 77.10%
Aromatase binding + 0.6343 63.43%
PPAR gamma + 0.8081 80.81%
Honey bee toxicity - 0.5680 56.80%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9698 96.98%

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 99.60% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.51% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.71% 96.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 97.08% 97.36%
CHEMBL218 P21554 Cannabinoid CB1 receptor 96.10% 96.61%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.21% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 94.03% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.99% 97.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 93.83% 82.69%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 92.43% 91.24%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.60% 92.94%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.31% 100.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 89.95% 96.21%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 89.87% 95.50%
CHEMBL2581 P07339 Cathepsin D 89.24% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.13% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.68% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.85% 93.04%
CHEMBL5255 O00206 Toll-like receptor 4 85.61% 92.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 85.16% 89.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.93% 89.00%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 84.22% 95.00%
CHEMBL2243 O00519 Anandamide amidohydrolase 83.31% 97.53%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.27% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.27% 95.56%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.25% 95.83%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.22% 96.77%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.97% 97.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.78% 94.45%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.34% 91.07%
CHEMBL5028 O14672 ADAM10 80.01% 97.50%

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.
Gynostemma pentaphyllum

Cross-Links

Top
PubChem 122179021
LOTUS LTS0027757
wikiData Q105238513