dihydroascorbigen 5'-O-beta-D-glucoside

Details

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Internal ID b630ebcf-1461-4ce9-8e08-5ade621cea85
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (3S,4R,5S)-3,4-dihydroxy-5-[(1S)-2-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3-(1H-indol-3-ylmethyl)oxolan-2-one
SMILES (Canonical) C1=CC=C2C(=C1)C(=CN2)CC3(C(C(OC3=O)C(CO)OC4C(C(C(C(O4)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC=C2C(=C1)C(=CN2)C[C@@]3([C@@H]([C@H](OC3=O)[C@H](CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
InChI InChI=1S/C21H27NO11/c23-7-12-14(25)15(26)16(27)19(31-12)32-13(8-24)17-18(28)21(30,20(29)33-17)5-9-6-22-11-4-2-1-3-10(9)11/h1-4,6,12-19,22-28,30H,5,7-8H2/t12-,13+,14-,15+,16-,17-,18-,19+,21+/m1/s1
InChI Key VYKGRASPXUUIKX-LGDVWLEWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H27NO11
Molecular Weight 469.40 g/mol
Exact Mass 469.15841068 g/mol
Topological Polar Surface Area (TPSA) 202.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -3.09
H-Bond Acceptor 11
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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5'-O-beta-D-glucosyl dihydroascorbigen
CHEBI:65277
Q27133778

2D Structure

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2D Structure of dihydroascorbigen 5'-O-beta-D-glucoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5781 57.81%
Caco-2 - 0.9026 90.26%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Lysosomes 0.3967 39.67%
OATP2B1 inhibitior - 0.8507 85.07%
OATP1B1 inhibitior + 0.9115 91.15%
OATP1B3 inhibitior + 0.9513 95.13%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.7031 70.31%
P-glycoprotein inhibitior - 0.7597 75.97%
P-glycoprotein substrate - 0.7726 77.26%
CYP3A4 substrate + 0.6509 65.09%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8346 83.46%
CYP3A4 inhibition - 0.9519 95.19%
CYP2C9 inhibition - 0.9363 93.63%
CYP2C19 inhibition - 0.8961 89.61%
CYP2D6 inhibition - 0.8977 89.77%
CYP1A2 inhibition - 0.7803 78.03%
CYP2C8 inhibition - 0.6924 69.24%
CYP inhibitory promiscuity - 0.7827 78.27%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5789 57.89%
Eye corrosion - 0.9928 99.28%
Eye irritation - 0.9577 95.77%
Skin irritation - 0.8243 82.43%
Skin corrosion - 0.9512 95.12%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4694 46.94%
Micronuclear + 0.6900 69.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.8577 85.77%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.6487 64.87%
Acute Oral Toxicity (c) III 0.5432 54.32%
Estrogen receptor binding + 0.8085 80.85%
Androgen receptor binding + 0.5228 52.28%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.5409 54.09%
Aromatase binding + 0.6666 66.66%
PPAR gamma + 0.7254 72.54%
Honey bee toxicity - 0.6813 68.13%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity - 0.7607 76.07%

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 99.61% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.32% 95.56%
CHEMBL2581 P07339 Cathepsin D 92.59% 98.95%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 91.10% 94.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.98% 89.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 90.87% 94.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.80% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.72% 94.00%
CHEMBL3310 Q96DB2 Histone deacetylase 11 89.83% 88.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.55% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 89.36% 92.62%
CHEMBL5103 Q969S8 Histone deacetylase 10 87.44% 90.08%
CHEMBL4040 P28482 MAP kinase ERK2 87.06% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.58% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.46% 99.23%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 84.21% 95.71%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.91% 95.83%
CHEMBL1937 Q92769 Histone deacetylase 2 82.89% 94.75%
CHEMBL213 P08588 Beta-1 adrenergic receptor 80.64% 95.56%

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.
Cardamine diphylla
Humulus lupulus

Cross-Links

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PubChem 46944661
LOTUS LTS0059615
wikiData Q105272456