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(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(E,2S)-6-hydroxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-4-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-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 49fbc8f3-66a5-4503-ae72-8b2a7e46eecc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(E,2S)-6-hydroxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-4-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)C)CC(C6C3(CCC6C(C)(CC=CC(C)(C)O)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)C)O)C)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C[C@H]([C@H]4[C@]3(CC[C@@H]4[C@](C)(C/C=C/C(C)(C)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@@H]6[C@@H]([C@@H]([C@H](CO6)O)O)O)O)O)O)C)O)C)(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
InChI InChI=1S/C53H90O23/c1-48(2,68)13-9-14-53(8,76-46-42(67)38(63)36(61)28(73-46)22-70-44-40(65)33(58)25(57)21-69-44)23-10-16-52(7)32(23)24(56)18-30-50(5)15-12-31(49(3,4)29(50)11-17-51(30,52)6)74-47-43(39(64)35(60)27(20-55)72-47)75-45-41(66)37(62)34(59)26(19-54)71-45/h9,13,23-47,54-68H,10-12,14-22H2,1-8H3/b13-9+/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-,50-,51+,52+,53-/m0/s1
InChI Key XILVLMRCUFMKSW-ZXBVKUNMSA-N
Popularity 0 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 -1.30
Atomic LogP (AlogP) -2.59
H-Bond Acceptor 23
H-Bond Donor 15
Rotatable Bonds 15

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)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(E,2S)-6-hydroxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-4-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-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 + 0.5819 58.19%
Caco-2 - 0.9043 90.43%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.6855 68.55%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8051 80.51%
OATP1B3 inhibitior + 0.8571 85.71%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.8192 81.92%
P-glycoprotein inhibitior + 0.7497 74.97%
P-glycoprotein substrate - 0.5634 56.34%
CYP3A4 substrate + 0.7435 74.35%
CYP2C9 substrate - 0.8007 80.07%
CYP2D6 substrate - 0.8411 84.11%
CYP3A4 inhibition - 0.9499 94.99%
CYP2C9 inhibition - 0.9049 90.49%
CYP2C19 inhibition - 0.9009 90.09%
CYP2D6 inhibition - 0.9549 95.49%
CYP1A2 inhibition - 0.9233 92.33%
CYP2C8 inhibition + 0.7368 73.68%
CYP inhibitory promiscuity - 0.9602 96.02%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6640 66.40%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9007 90.07%
Skin irritation - 0.6582 65.82%
Skin corrosion - 0.9524 95.24%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8463 84.63%
Micronuclear - 0.8900 89.00%
Hepatotoxicity + 0.5531 55.31%
skin sensitisation - 0.9219 92.19%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.8568 85.68%
Acute Oral Toxicity (c) I 0.6662 66.62%
Estrogen receptor binding + 0.7892 78.92%
Androgen receptor binding + 0.7428 74.28%
Thyroid receptor binding + 0.5823 58.23%
Glucocorticoid receptor binding + 0.7545 75.45%
Aromatase binding + 0.6419 64.19%
PPAR gamma + 0.7955 79.55%
Honey bee toxicity - 0.5758 57.58%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8873 88.73%

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 98.88% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.79% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 97.23% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.55% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.78% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.44% 96.61%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.56% 92.94%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 90.24% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.02% 86.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.99% 82.69%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 86.45% 95.50%
CHEMBL1977 P11473 Vitamin D receptor 86.23% 99.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.99% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.98% 95.89%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.95% 97.36%
CHEMBL2996 Q05655 Protein kinase C delta 85.66% 97.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.24% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.92% 97.14%
CHEMBL5028 O14672 ADAM10 82.07% 97.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.69% 92.62%
CHEMBL2581 P07339 Cathepsin D 81.56% 98.95%
CHEMBL1871 P10275 Androgen Receptor 81.55% 96.43%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 80.91% 95.58%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.62% 100.00%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 80.45% 92.88%
CHEMBL1937 Q92769 Histone deacetylase 2 80.40% 94.75%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.22% 100.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.20% 96.77%

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 154496708
LOTUS LTS0034101
wikiData Q105328572