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(2S,3R,4R,5R,6S)-2-[(3R,4S,5S)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-[[(2R,5R,7S,10R,11R,14R,15S,16S,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-3-yl]oxy-6-methyloxane-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 21362d87-e4fe-45ad-b30e-31badd32d93d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3R,4R,5R,6S)-2-[(3R,4S,5S)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-[[(2R,5R,7S,10R,11R,14R,15S,16S,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C7C(CC(OC78CC6(C5(CCC4C3(C)C)C)CO8)C=C(C)C)(C)O)C)O)OC9C(C(C(C(O9)COC1C(C(C(C(O1)CO)O)O)O)O)O)OC1C(C(C(CO1)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](COC2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H]7[C@@](C[C@@H](O[C@@]78CC6([C@@]5(CC[C@H]4C3(C)C)C)CO8)C=C(C)C)(C)O)C)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O)O
InChI InChI=1S/C58H94O26/c1-23(2)15-25-16-56(8,72)47-26-9-10-32-54(6)13-12-33(53(4,5)31(54)11-14-55(32,7)57(26)21-58(47,84-25)76-22-57)80-51-46(83-50-43(71)38(66)34(62)24(3)77-50)44(28(61)19-74-51)81-52-45(82-49-41(69)35(63)27(60)18-73-49)40(68)37(65)30(79-52)20-75-48-42(70)39(67)36(64)29(17-59)78-48/h15,24-52,59-72H,9-14,16-22H2,1-8H3/t24-,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-,50-,51?,52-,54-,55+,56-,57?,58-/m0/s1
InChI Key KVKRFLVYJLIZFD-LQRLABOESA-N
Popularity 43 references in papers

Physical and Chemical Properties

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Molecular Formula C58H94O26
Molecular Weight 1207.30 g/mol
Exact Mass 1206.60333310 g/mol
Topological Polar Surface Area (TPSA) 394.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -2.72
H-Bond Acceptor 26
H-Bond Donor 14
Rotatable Bonds 13

Synonyms

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Jujuboside-A
(3beta,16beta,23R)-16,23:16,30-Diepoxy-20-hydroxydammar-24-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O0[O-beta-D-glucopyranosyl-(1->6)-O-[beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->3)]-alpha-L-arabinopyranoside

2D Structure

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2D Structure of (2S,3R,4R,5R,6S)-2-[(3R,4S,5S)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-[[(2R,5R,7S,10R,11R,14R,15S,16S,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]oxan-3-yl]oxy-6-methyloxane-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 + 0.7395 73.95%
Caco-2 - 0.8796 87.96%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7487 74.87%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8251 82.51%
OATP1B3 inhibitior + 0.8885 88.85%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.8449 84.49%
P-glycoprotein inhibitior + 0.7461 74.61%
P-glycoprotein substrate + 0.6409 64.09%
CYP3A4 substrate + 0.7547 75.47%
CYP2C9 substrate - 0.7915 79.15%
CYP2D6 substrate - 0.8348 83.48%
CYP3A4 inhibition - 0.9226 92.26%
CYP2C9 inhibition - 0.8642 86.42%
CYP2C19 inhibition - 0.9010 90.10%
CYP2D6 inhibition - 0.9274 92.74%
CYP1A2 inhibition - 0.9012 90.12%
CYP2C8 inhibition + 0.7787 77.87%
CYP inhibitory promiscuity - 0.9197 91.97%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5717 57.17%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9004 90.04%
Skin irritation - 0.5769 57.69%
Skin corrosion - 0.9449 94.49%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8130 81.30%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.8994 89.94%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity - 0.9022 90.22%
Acute Oral Toxicity (c) I 0.6698 66.98%
Estrogen receptor binding + 0.8063 80.63%
Androgen receptor binding + 0.7579 75.79%
Thyroid receptor binding + 0.5791 57.91%
Glucocorticoid receptor binding + 0.7618 76.18%
Aromatase binding + 0.6631 66.31%
PPAR gamma + 0.8073 80.73%
Honey bee toxicity - 0.5805 58.05%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9306 93.06%

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 97.81% 91.11%
CHEMBL325 Q13547 Histone deacetylase 1 97.67% 95.92%
CHEMBL226 P30542 Adenosine A1 receptor 97.05% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.01% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 96.27% 96.61%
CHEMBL1937 Q92769 Histone deacetylase 2 95.89% 94.75%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.39% 97.25%
CHEMBL2581 P07339 Cathepsin D 91.80% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.74% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 91.72% 90.17%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 91.46% 95.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 90.66% 89.05%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 90.39% 91.24%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.87% 89.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 88.68% 97.36%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.64% 92.94%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.34% 100.00%
CHEMBL3589 P55263 Adenosine kinase 87.37% 98.05%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 87.36% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.82% 86.33%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.88% 98.75%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 85.50% 97.86%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.80% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.41% 95.89%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 83.65% 97.47%
CHEMBL2094128 P24941 Cyclin-dependent kinase 2/cyclin A 83.47% 97.25%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.92% 92.62%
CHEMBL3524 P56524 Histone deacetylase 4 82.86% 92.97%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.75% 100.00%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 82.71% 95.36%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.59% 97.14%
CHEMBL259 P32245 Melanocortin receptor 4 82.38% 95.38%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.15% 94.00%
CHEMBL5555 O00767 Acyl-CoA desaturase 81.05% 97.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.84% 95.56%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.67% 97.28%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.09% 82.69%

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.
Ziziphus jujuba

Cross-Links

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PubChem 171446
NPASS NPC196042