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(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-2,12-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-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 4f1d3c8e-707b-4453-9a58-0635375c11d7
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-2,12-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC(=CCCC(C)(C1CCC2(C1(C(CC3C2CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)O)C)O)C)C)OC7C(C(C(C(O7)CO)O)O)O)C
SMILES (Isomeric) CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@]1([C@@H](C[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H]([C@@H](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)O)C)O)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C
InChI InChI=1S/C48H82O19/c1-21(2)10-9-14-47(7,67-42-38(61)35(58)32(55)26(19-50)63-42)29-13-15-46(6)22-11-12-28-44(3,4)40(24(52)17-45(28,5)23(22)16-30(53)48(29,46)8)66-43-39(36(59)33(56)27(20-51)64-43)65-41-37(60)34(57)31(54)25(18-49)62-41/h10,22-43,49-61H,9,11-20H2,1-8H3/t22-,23+,24-,25-,26-,27-,28+,29-,30-,31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+,43+,45-,46+,47+,48+/m1/s1
InChI Key CYPYEPJSRSWKLA-FUJAQZIBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C48H82O19
Molecular Weight 963.20 g/mol
Exact Mass 962.54503038 g/mol
Topological Polar Surface Area (TPSA) 318.00 Ų
XlogP 1.40
Atomic LogP (AlogP) -1.06
H-Bond Acceptor 19
H-Bond Donor 13
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(2R,3R,5R,8R,9S,10R,12R,13R,14S,17S)-2,12-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-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 - 0.9009 90.09%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7251 72.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8473 84.73%
OATP1B3 inhibitior + 0.8189 81.89%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.7700 77.00%
P-glycoprotein inhibitior + 0.7556 75.56%
P-glycoprotein substrate - 0.5437 54.37%
CYP3A4 substrate + 0.7300 73.00%
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 + 0.6690 66.90%
CYP inhibitory promiscuity - 0.9413 94.13%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6474 64.74%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9048 90.48%
Skin irritation - 0.5956 59.56%
Skin corrosion - 0.9488 94.88%
Ames mutagenesis - 0.6624 66.24%
Human Ether-a-go-go-Related Gene inhibition + 0.8227 82.27%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.5705 57.05%
skin sensitisation - 0.8991 89.91%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.5875 58.75%
Nephrotoxicity - 0.8037 80.37%
Acute Oral Toxicity (c) I 0.5677 56.77%
Estrogen receptor binding + 0.7856 78.56%
Androgen receptor binding + 0.7594 75.94%
Thyroid receptor binding - 0.5298 52.98%
Glucocorticoid receptor binding + 0.6993 69.93%
Aromatase binding + 0.6508 65.08%
PPAR gamma + 0.7897 78.97%
Honey bee toxicity - 0.5630 56.30%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5100 51.00%
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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.68% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.16% 97.25%
CHEMBL206 P03372 Estrogen receptor alpha 95.36% 97.64%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.87% 97.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 93.69% 96.21%
CHEMBL3714130 P46095 G-protein coupled receptor 6 93.42% 97.36%
CHEMBL5608 Q16288 NT-3 growth factor receptor 92.79% 95.89%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.41% 94.45%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 92.33% 95.50%
CHEMBL218 P21554 Cannabinoid CB1 receptor 92.11% 96.61%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 92.06% 91.24%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.48% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.45% 96.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 89.42% 96.38%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.55% 85.14%
CHEMBL226 P30542 Adenosine A1 receptor 88.16% 95.93%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 88.07% 91.03%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 87.89% 97.86%
CHEMBL233 P35372 Mu opioid receptor 87.67% 97.93%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.89% 97.14%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 86.06% 95.71%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 85.74% 95.58%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.58% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 84.57% 94.75%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.98% 93.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 83.58% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 83.28% 97.79%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 83.07% 96.90%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.66% 92.94%
CHEMBL259 P32245 Melanocortin receptor 4 82.53% 95.38%
CHEMBL5555 O00767 Acyl-CoA desaturase 82.51% 97.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.31% 94.33%
CHEMBL2243 O00519 Anandamide amidohydrolase 81.71% 97.53%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.64% 98.99%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.57% 89.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.52% 95.89%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 81.33% 97.50%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 80.89% 97.47%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.44% 96.77%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 80.44% 92.86%

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 163000202
LOTUS LTS0265801
wikiData Q104972486