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Ardisianoside A

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 816e53cd-7713-4613-9387-7d8662764578
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6S)-5-hydroxy-6-[(2S,3R,4S,5R,6R)-5-hydroxy-2-[(3S,4S,5R,6S)-4-hydroxy-6-[[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R)-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-4-yl]oxy-2-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC1(CCC23COC4(C2C1)CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(CO7)OC8C(C(C(C(O8)CO)O)OC9C(C(C(C(O9)CO)OC1C(C(C(C(O1)CO)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)OC1C(C(C(CO1)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC[C@@]45[C@]3(C[C@H]([C@@]6([C@H]4CC(CC6)(C)C)CO5)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@H](CO7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI InChI=1S/C70H116O36/c1-64(2)14-15-69-25-94-70(35(69)16-64)13-9-34-66(5)11-10-37(65(3,4)33(66)8-12-67(34,6)68(70,7)17-36(69)77)101-62-55(105-60-50(90)46(86)41(81)29(20-73)97-60)43(83)32(24-93-62)100-63-56(106-57-47(87)38(78)26(76)23-92-57)53(42(82)30(21-74)98-63)103-61-51(91)54(104-59-49(89)45(85)40(80)28(19-72)96-59)52(31(22-75)99-61)102-58-48(88)44(84)39(79)27(18-71)95-58/h26-63,71-91H,8-25H2,1-7H3/t26-,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-,53+,54-,55-,56-,57+,58+,59+,60+,61+,62+,63+,66+,67-,68+,69-,70+/m1/s1
InChI Key YRTDPWGTGFRWCS-NVSDYHLPSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C70H116O36
Molecular Weight 1533.60 g/mol
Exact Mass 1532.7246300 g/mol
Topological Polar Surface Area (TPSA) 563.00 Ų
XlogP -4.90
Atomic LogP (AlogP) -7.60
H-Bond Acceptor 36
H-Bond Donor 21
Rotatable Bonds 19

Synonyms

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CHEBI:65425
(-)-ardisianoside A
ARDISIANOSIDES A
CHEMBL374091
Q27133869
(3beta,16alpha)-16-hydroxy-13,28-epoxyoleanan-3-yl beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)-[beta-D-glucopyranosyl-(1->4)]-beta-D-glucopyranosyl-(1->3)-[beta-D-xylopyranosyl-(1->2)]-beta-D-glucopyranosyl-(1->4)]-alpha-L-arabinopyranoside
3beta-O-beta-D-Glcp-(1->2)-{beta-D-Xylp-(1->2)-{beta-D-Glcp-(1->3)-[beta-D-Glcp-(1->4)]-beta-D-Glcp-(1->3)}-beta-D-Glcp-(1->4)}-alpha-L-Arap-13beta,28-epoxy-16alpha-hydroxyoleanane
3beta-O-beta-D-glucopyranosyl-(1->2)-{beta-D-xylopyranosyl-(1->2)-{beta-D-glucopyranosyl-(1->3)-[beta-D-glucopyranosyl-(1->4)]-beta-D-glucopyranosyl-(1->3)}-beta-D-glucopyranosyl-(1->4)}-alpha-L-arabinopyranosyl-13beta,28-epoxy-16alpha-hydroxyoleanane

2D Structure

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2D Structure of Ardisianoside A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5489 54.89%
Caco-2 - 0.8692 86.92%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.6239 62.39%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8000 80.00%
OATP1B3 inhibitior + 0.9351 93.51%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.5250 52.50%
BSEP inhibitior + 0.8562 85.62%
P-glycoprotein inhibitior + 0.7431 74.31%
P-glycoprotein substrate + 0.5474 54.74%
CYP3A4 substrate + 0.7447 74.47%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8237 82.37%
CYP3A4 inhibition - 0.9474 94.74%
CYP2C9 inhibition - 0.8579 85.79%
CYP2C19 inhibition - 0.8572 85.72%
CYP2D6 inhibition - 0.9505 95.05%
CYP1A2 inhibition - 0.9122 91.22%
CYP2C8 inhibition + 0.7194 71.94%
CYP inhibitory promiscuity - 0.9632 96.32%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6416 64.16%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.8974 89.74%
Skin irritation - 0.7052 70.52%
Skin corrosion - 0.9482 94.82%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8053 80.53%
Micronuclear - 0.9000 90.00%
Hepatotoxicity - 0.7875 78.75%
skin sensitisation - 0.9225 92.25%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.8662 86.62%
Acute Oral Toxicity (c) I 0.7071 70.71%
Estrogen receptor binding + 0.7974 79.74%
Androgen receptor binding + 0.7552 75.52%
Thyroid receptor binding + 0.6083 60.83%
Glucocorticoid receptor binding + 0.7460 74.60%
Aromatase binding + 0.6592 65.92%
PPAR gamma + 0.8003 80.03%
Honey bee toxicity - 0.5842 58.42%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.8283 82.83%

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 94.95% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.02% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 93.24% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.59% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.39% 94.45%
CHEMBL4302 P08183 P-glycoprotein 1 90.17% 92.98%
CHEMBL2581 P07339 Cathepsin D 89.01% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.66% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 88.18% 91.24%
CHEMBL233 P35372 Mu opioid receptor 87.86% 97.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.81% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.37% 95.50%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 87.05% 95.58%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 86.96% 92.88%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.22% 92.94%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 85.43% 91.03%
CHEMBL1937 Q92769 Histone deacetylase 2 84.71% 94.75%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 84.48% 95.17%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.27% 96.21%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 84.25% 97.86%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 84.02% 100.00%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 83.29% 98.99%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 83.26% 96.38%
CHEMBL259 P32245 Melanocortin receptor 4 83.15% 95.38%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 81.79% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.77% 97.28%
CHEMBL2095194 P08709 Coagulation factor VII/tissue factor 80.20% 99.17%

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.
Ardisia japonica

Cross-Links

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PubChem 16109779
NPASS NPC106701
ChEMBL CHEMBL374091
LOTUS LTS0093266
wikiData Q27133869