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(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[2-[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-12-hydroxy-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

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 a7c482b4-dc49-4ea3-b24f-fa212a0b32a3
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[2-[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-12-hydroxy-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)O)C)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)C
SMILES (Isomeric) CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3CCC(C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)C
InChI InChI=1S/C53H90O23/c1-22(2)9-8-14-53(7,76-48-44(68)40(64)37(61)31(73-48)21-69-46-42(66)38(62)34(58)28(18-54)70-46)25-13-16-52(6)33(25)27(57)17-26-23-10-11-32(50(3,4)24(23)12-15-51(26,52)5)74-49-45(41(65)36(60)30(20-56)72-49)75-47-43(67)39(63)35(59)29(19-55)71-47/h9,23-49,54-68H,8,10-21H2,1-7H3/t23?,24?,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?/m1/s1
InChI Key GWGMUMCHLXLHTC-QWTSXOHBSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C53H90O23
Molecular Weight 1095.30 g/mol
Exact Mass 1094.58728911 g/mol
Topological Polar Surface Area (TPSA) 377.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -2.59
H-Bond Acceptor 23
H-Bond Donor 15
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[2-[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-12-hydroxy-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6877 68.77%
Caco-2 - 0.9271 92.71%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.7251 72.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8169 81.69%
OATP1B3 inhibitior + 0.8189 81.89%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.8860 88.60%
P-glycoprotein inhibitior + 0.7506 75.06%
P-glycoprotein substrate - 0.5749 57.49%
CYP3A4 substrate + 0.7315 73.15%
CYP2C9 substrate - 0.8025 80.25%
CYP2D6 substrate - 0.8264 82.64%
CYP3A4 inhibition - 0.9502 95.02%
CYP2C9 inhibition - 0.8671 86.71%
CYP2C19 inhibition - 0.9036 90.36%
CYP2D6 inhibition - 0.9380 93.80%
CYP1A2 inhibition - 0.9057 90.57%
CYP2C8 inhibition + 0.6997 69.97%
CYP inhibitory promiscuity - 0.9413 94.13%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6474 64.74%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9019 90.19%
Skin irritation - 0.5956 59.56%
Skin corrosion - 0.9488 94.88%
Ames mutagenesis - 0.8200 82.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8567 85.67%
Micronuclear - 0.8800 88.00%
Hepatotoxicity + 0.5532 55.32%
skin sensitisation - 0.8991 89.91%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.5875 58.75%
Nephrotoxicity - 0.6475 64.75%
Acute Oral Toxicity (c) I 0.5677 56.77%
Estrogen receptor binding + 0.8064 80.64%
Androgen receptor binding + 0.7634 76.34%
Thyroid receptor binding + 0.5483 54.83%
Glucocorticoid receptor binding + 0.7352 73.52%
Aromatase binding + 0.6484 64.84%
PPAR gamma + 0.7913 79.13%
Honey bee toxicity - 0.5336 53.36%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9172 91.72%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.01% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.96% 91.11%
CHEMBL218 P21554 Cannabinoid CB1 receptor 96.43% 96.61%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.15% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.57% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 93.03% 95.93%
CHEMBL2996 Q05655 Protein kinase C delta 92.45% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.69% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.29% 100.00%
CHEMBL259 P32245 Melanocortin receptor 4 89.42% 95.38%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.98% 94.45%
CHEMBL3714130 P46095 G-protein coupled receptor 6 88.86% 97.36%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 88.56% 95.50%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 87.54% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.76% 97.14%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.29% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.26% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 84.24% 93.04%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.22% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 83.90% 94.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.20% 85.14%
CHEMBL2581 P07339 Cathepsin D 82.76% 98.95%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.35% 100.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.21% 100.00%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.80% 96.90%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.77% 92.62%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.49% 95.83%
CHEMBL5028 O14672 ADAM10 80.11% 97.50%

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.
Gynostemma pentaphyllum

Cross-Links

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PubChem 11968560
NPASS NPC10798
LOTUS LTS0172914
wikiData Q105107472