1-O-beta-D-Glucopyranosyl anthranilate

Details

Top
Internal ID dc800564-0d5f-4be8-9822-067e98931ef5
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses
IUPAC Name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-aminobenzoate
SMILES (Canonical) C1=CC=C(C(=C1)C(=O)OC2C(C(C(C(O2)CO)O)O)O)N
SMILES (Isomeric) C1=CC=C(C(=C1)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)N
InChI InChI=1S/C13H17NO7/c14-7-4-2-1-3-6(7)12(19)21-13-11(18)10(17)9(16)8(5-15)20-13/h1-4,8-11,13,15-18H,5,14H2/t8-,9-,10+,11-,13+/m1/s1
InChI Key GTQKOJVFDJDUGN-HMUNZLOLSA-N
Popularity 4 references in papers

Physical and Chemical Properties

Top
Molecular Formula C13H17NO7
Molecular Weight 299.28 g/mol
Exact Mass 299.10050188 g/mol
Topological Polar Surface Area (TPSA) 143.00 Ų
XlogP -0.50
Atomic LogP (AlogP) -1.77
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

Top
Anthranilic acid glucosyl
D-Glucose 1-anthranilate
anthranilate-beta-glucoside
anthraniloyl-O-glucopyranose
anthranilic acid-beta-glucoside
beta-Glucopyranosyl anthranilate
CHEMBL2063298
CHEBI:176467
2-aminobenzoic acid-beta-glucoside
1-O-beta-D-Glucopyranosyl anthranilate
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of 1-O-beta-D-Glucopyranosyl anthranilate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.8792 87.92%
Caco-2 - 0.8513 85.13%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Nucleus 0.4938 49.38%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9141 91.41%
OATP1B3 inhibitior + 0.9275 92.75%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.9801 98.01%
P-glycoprotein inhibitior - 0.9334 93.34%
P-glycoprotein substrate - 0.9547 95.47%
CYP3A4 substrate - 0.5594 55.94%
CYP2C9 substrate - 0.5978 59.78%
CYP2D6 substrate - 0.8380 83.80%
CYP3A4 inhibition - 0.8870 88.70%
CYP2C9 inhibition - 0.8210 82.10%
CYP2C19 inhibition - 0.7389 73.89%
CYP2D6 inhibition - 0.9021 90.21%
CYP1A2 inhibition - 0.8421 84.21%
CYP2C8 inhibition - 0.7271 72.71%
CYP inhibitory promiscuity - 0.8083 80.83%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6728 67.28%
Eye corrosion - 0.9934 99.34%
Eye irritation - 0.8244 82.44%
Skin irritation - 0.8351 83.51%
Skin corrosion - 0.9636 96.36%
Ames mutagenesis - 0.8054 80.54%
Human Ether-a-go-go-Related Gene inhibition - 0.7026 70.26%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.8515 85.15%
Respiratory toxicity - 0.6222 62.22%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.6484 64.84%
Acute Oral Toxicity (c) III 0.6108 61.08%
Estrogen receptor binding - 0.6919 69.19%
Androgen receptor binding - 0.5742 57.42%
Thyroid receptor binding - 0.5949 59.49%
Glucocorticoid receptor binding - 0.5706 57.06%
Aromatase binding - 0.6540 65.40%
PPAR gamma + 0.5690 56.90%
Honey bee toxicity - 0.8535 85.35%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.7300 73.00%
Fish aquatic toxicity - 0.6809 68.09%

Targets

Top

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 97.92% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.43% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 88.86% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.92% 97.09%
CHEMBL2581 P07339 Cathepsin D 84.41% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.35% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.69% 95.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.56% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.15% 99.17%

Plants that contains it

Top
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.
Bromelia karatas
Isatis tinctoria

Cross-Links

Top
PubChem 70684367
NPASS NPC112534
LOTUS LTS0216648
wikiData Q76754315