(2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1S,3aR,9aR,11S,11aS)-7-{[(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]oxy}oxan-2-yl]oxy}-11-hydroxy-3a,6,6,9a-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-4,6-dimethylhept-5-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID e9b6da4c-81b1-4e6c-b764-50cb93d6c271
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(10R,12S,13S,14R,17S)-17-[(2S)-4,6-dimethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-hydroxy-4,4,10,14-tetramethyl-1,2,3,5,6,7,8,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC(CC(C)(C1CCC2(C1C(CC3C2CCC4C3(CCC(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)CO)O)O)O)C=C(C)C
SMILES (Isomeric) CC(C[C@@](C)([C@H]1CC[C@]2([C@H]1[C@H](CC3C2CCC4[C@@]3(CCC(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)O)O)O)C=C(C)C
InChI InChI=1S/C48H82O18/c1-21(2)15-22(3)17-48(8,66-43-40(60)37(57)34(54)28(19-50)62-43)24-11-13-47(7)23-9-10-30-45(4,5)31(12-14-46(30,6)25(23)16-26(52)32(24)47)64-44-41(38(58)35(55)29(20-51)63-44)65-42-39(59)36(56)33(53)27(18-49)61-42/h15,22-44,49-60H,9-14,16-20H2,1-8H3/t22?,23?,24-,25?,26-,27+,28+,29+,30?,31?,32+,33+,34+,35+,36-,37-,38-,39+,40+,41+,42-,43-,44-,46+,47+,48-/m0/s1
InChI Key IRBVCFDYIGGFFY-ADSMOORZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C48H82O18
Molecular Weight 947.20 g/mol
Exact Mass 946.55011576 g/mol
Topological Polar Surface Area (TPSA) 298.00 Ų
XlogP 2.40
Atomic LogP (AlogP) -0.17
H-Bond Acceptor 18
H-Bond Donor 12
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-{[(2S)-2-[(1S,3aR,9aR,11S,11aS)-7-{[(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]oxy}oxan-2-yl]oxy}-11-hydroxy-3a,6,6,9a-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-4,6-dimethylhept-5-en-2-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 - 0.9006 90.06%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.7251 72.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8308 83.08%
OATP1B3 inhibitior + 0.8189 81.89%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.7050 70.50%
P-glycoprotein inhibitior + 0.7609 76.09%
P-glycoprotein substrate - 0.6083 60.83%
CYP3A4 substrate + 0.7299 72.99%
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 + 0.6365 63.65%
CYP inhibitory promiscuity - 0.9413 94.13%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6474 64.74%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9054 90.54%
Skin irritation - 0.5956 59.56%
Skin corrosion - 0.9488 94.88%
Ames mutagenesis - 0.7900 79.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8450 84.50%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.5739 57.39%
skin sensitisation - 0.8991 89.91%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.5875 58.75%
Nephrotoxicity - 0.8289 82.89%
Acute Oral Toxicity (c) I 0.5677 56.77%
Estrogen receptor binding + 0.8075 80.75%
Androgen receptor binding + 0.7391 73.91%
Thyroid receptor binding - 0.5302 53.02%
Glucocorticoid receptor binding + 0.6966 69.66%
Aromatase binding + 0.6729 67.29%
PPAR gamma + 0.7826 78.26%
Honey bee toxicity - 0.5203 52.03%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5700 57.00%
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 98.08% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.10% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.00% 97.25%
CHEMBL226 P30542 Adenosine A1 receptor 92.26% 95.93%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.26% 94.45%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 92.24% 96.21%
CHEMBL2581 P07339 Cathepsin D 92.05% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 92.01% 97.79%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 91.75% 95.58%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.98% 95.89%
CHEMBL218 P21554 Cannabinoid CB1 receptor 90.46% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.40% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.62% 85.14%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.93% 96.38%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.33% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.77% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.69% 95.89%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 86.58% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.61% 97.14%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 84.82% 92.86%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 84.71% 97.29%
CHEMBL2179 P04062 Beta-glucocerebrosidase 84.70% 85.31%
CHEMBL206 P03372 Estrogen receptor alpha 84.09% 97.64%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.95% 100.00%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 83.16% 95.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.71% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.70% 97.36%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 81.75% 96.09%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.72% 93.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.68% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.49% 92.62%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 80.01% 95.50%

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 3036963
NPASS NPC269298