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Atractyloside I

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 d1a473cf-99da-4132-bff8-67578c755b6a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name (4aR,6R,8aS)-4,8a-dimethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-1,4a,5,6,7,8-hexahydronaphthalen-2-one
SMILES (Canonical) CC1=C(C(=O)CC2(C1CC(CC2)C(C)(C)OC3C(C(C(C(O3)CO)O)O)O)C)OC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) CC1=C(C(=O)C[C@]2([C@H]1C[C@@H](CC2)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChI InChI=1S/C27H44O13/c1-11-13-7-12(26(2,3)40-25-22(36)20(34)18(32)16(10-29)38-25)5-6-27(13,4)8-14(30)23(11)39-24-21(35)19(33)17(31)15(9-28)37-24/h12-13,15-22,24-25,28-29,31-36H,5-10H2,1-4H3/t12-,13+,15-,16-,17-,18-,19+,20+,21-,22-,24+,25+,27+/m1/s1
InChI Key XMFJYFXSIKDRHJ-OJGKPVIHSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C27H44O13
Molecular Weight 576.60 g/mol
Exact Mass 576.27819145 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -1.93
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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(4aR,6R,8aS)-4,8a-dimethyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-1,4a,5,6,7,8-hexahydronaphthalen-2-one
(4aR,6R,8aS)-4,8a-dimethyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-6-(2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxypropan-2-yl)-1,4a,5,6,7,8-hexahydronaphthalen-2-one
RefChem:115479
CHEBI:190270
C17866

2D Structure

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2D Structure of Atractyloside I

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6777 67.77%
Caco-2 - 0.8719 87.19%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8576 85.76%
OATP2B1 inhibitior - 0.7213 72.13%
OATP1B1 inhibitior + 0.8896 88.96%
OATP1B3 inhibitior - 0.4346 43.46%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.6276 62.76%
BSEP inhibitior - 0.6641 66.41%
P-glycoprotein inhibitior - 0.4461 44.61%
P-glycoprotein substrate - 0.8187 81.87%
CYP3A4 substrate + 0.6845 68.45%
CYP2C9 substrate - 0.7960 79.60%
CYP2D6 substrate - 0.8770 87.70%
CYP3A4 inhibition - 0.9618 96.18%
CYP2C9 inhibition - 0.8655 86.55%
CYP2C19 inhibition - 0.8815 88.15%
CYP2D6 inhibition - 0.9421 94.21%
CYP1A2 inhibition - 0.8571 85.71%
CYP2C8 inhibition - 0.6625 66.25%
CYP inhibitory promiscuity - 0.9397 93.97%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6699 66.99%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9338 93.38%
Skin irritation - 0.6624 66.24%
Skin corrosion - 0.9543 95.43%
Ames mutagenesis - 0.5885 58.85%
Human Ether-a-go-go-Related Gene inhibition - 0.3932 39.32%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.5324 53.24%
skin sensitisation - 0.8932 89.32%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity - 0.7375 73.75%
Nephrotoxicity + 0.5246 52.46%
Acute Oral Toxicity (c) III 0.7297 72.97%
Estrogen receptor binding + 0.6437 64.37%
Androgen receptor binding + 0.6106 61.06%
Thyroid receptor binding - 0.5454 54.54%
Glucocorticoid receptor binding + 0.5754 57.54%
Aromatase binding + 0.6159 61.59%
PPAR gamma + 0.5654 56.54%
Honey bee toxicity - 0.6987 69.87%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9554 95.54%

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 98.86% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.61% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.80% 97.09%
CHEMBL220 P22303 Acetylcholinesterase 94.96% 94.45%
CHEMBL2581 P07339 Cathepsin D 94.93% 98.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.51% 96.61%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.22% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.64% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 89.44% 97.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.48% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.63% 85.14%
CHEMBL259 P32245 Melanocortin receptor 4 87.49% 95.38%
CHEMBL3524 P56524 Histone deacetylase 4 87.35% 92.97%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.08% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 87.08% 94.75%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.58% 96.77%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.58% 97.14%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 86.09% 96.21%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.81% 93.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.57% 93.04%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.84% 94.45%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 84.83% 90.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.42% 94.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.74% 92.50%
CHEMBL1871 P10275 Androgen Receptor 81.70% 96.43%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.56% 100.00%
CHEMBL5103 Q969S8 Histone deacetylase 10 80.50% 90.08%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.32% 86.33%

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.
Atractylodes lancea

Cross-Links

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PubChem 10929902
NPASS NPC163063
LOTUS LTS0155565
wikiData Q105330696