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Atroviolaceoside

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 1497929e-3b4d-4b4c-b72d-9953b081d609
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
IUPAC Name (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13R,15R,16R,18S,19R)-15,19-dihydroxy-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) CC1C2C(CC3C2(CCC4C3CC(C5C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)O)C)OC18CCC(CO8)CO
SMILES (Isomeric) C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@H]([C@@H]5[C@@]4(C[C@H]([C@@H](C5)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C)O)C)O[C@]18CC[C@H](CO8)CO
InChI InChI=1S/C39H64O16/c1-16-28-25(55-39(16)7-4-17(12-40)15-50-39)9-20-18-8-22(43)21-10-24(23(44)11-38(21,3)19(18)5-6-37(20,28)2)51-35-33(49)31(47)34(27(14-42)53-35)54-36-32(48)30(46)29(45)26(13-41)52-36/h16-36,40-49H,4-15H2,1-3H3/t16-,17-,18+,19-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,31+,32+,33+,34-,35+,36-,37-,38+,39+/m0/s1
InChI Key UPXMNFSCVVTVFO-IZISHBDUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H64O16
Molecular Weight 788.90 g/mol
Exact Mass 788.41943595 g/mol
Topological Polar Surface Area (TPSA) 258.00 Ų
XlogP -0.80
Atomic LogP (AlogP) -1.64
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 7

Synonyms

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CHEMBL449185
(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-6-[(1R,2S,4S,5'S,6R,7S,8R,9S,12S,13R,15R,16R,18S,19R)-15,19-dihydroxy-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

2D Structure

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2D Structure of Atroviolaceoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5246 52.46%
Caco-2 - 0.8864 88.64%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.6174 61.74%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8826 88.26%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.6250 62.50%
BSEP inhibitior - 0.7093 70.93%
P-glycoprotein inhibitior + 0.6977 69.77%
P-glycoprotein substrate - 0.6573 65.73%
CYP3A4 substrate + 0.7443 74.43%
CYP2C9 substrate - 0.8054 80.54%
CYP2D6 substrate - 0.8164 81.64%
CYP3A4 inhibition - 0.9473 94.73%
CYP2C9 inhibition - 0.9215 92.15%
CYP2C19 inhibition - 0.8997 89.97%
CYP2D6 inhibition - 0.9561 95.61%
CYP1A2 inhibition - 0.9215 92.15%
CYP2C8 inhibition + 0.6665 66.65%
CYP inhibitory promiscuity - 0.9616 96.16%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6223 62.23%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9180 91.80%
Skin irritation - 0.6555 65.55%
Skin corrosion - 0.9521 95.21%
Ames mutagenesis - 0.7570 75.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7623 76.23%
Micronuclear - 0.9100 91.00%
Hepatotoxicity - 0.8601 86.01%
skin sensitisation - 0.9420 94.20%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity - 0.5375 53.75%
Nephrotoxicity - 0.8577 85.77%
Acute Oral Toxicity (c) I 0.8185 81.85%
Estrogen receptor binding + 0.7668 76.68%
Androgen receptor binding + 0.7074 70.74%
Thyroid receptor binding - 0.6252 62.52%
Glucocorticoid receptor binding - 0.5102 51.02%
Aromatase binding + 0.6444 64.44%
PPAR gamma + 0.6808 68.08%
Honey bee toxicity - 0.5664 56.64%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.7523 75.23%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.34% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 96.69% 96.61%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.45% 91.11%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 94.67% 96.21%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.69% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 92.56% 95.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.23% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.68% 97.25%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 90.55% 95.50%
CHEMBL237 P41145 Kappa opioid receptor 88.46% 98.10%
CHEMBL220 P22303 Acetylcholinesterase 87.38% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.19% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.43% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.87% 85.14%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.19% 95.83%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 81.63% 95.58%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.73% 96.77%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.60% 91.24%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 80.49% 92.86%
CHEMBL3922 P50579 Methionine aminopeptidase 2 80.37% 97.28%

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.
Allium atroviolaceum

Cross-Links

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PubChem 11614761
LOTUS LTS0261262
wikiData Q105277044