(2S)-6-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-1,4-benzoxazin-3-one

Details

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Internal ID 4cc6f7fe-5355-413b-9e79-c8a43779d77c
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (2S)-6-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-1,4-benzoxazin-3-one
SMILES (Canonical) C1=CC2=C(C=C1O)NC(=O)C(O2)OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric) C1=CC2=C(C=C1O)NC(=O)[C@@H](O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C14H17NO9/c16-4-8-9(18)10(19)11(20)13(23-8)24-14-12(21)15-6-3-5(17)1-2-7(6)22-14/h1-3,8-11,13-14,16-20H,4H2,(H,15,21)/t8-,9-,10+,11-,13+,14+/m1/s1
InChI Key UPXZXCWEGZCJJW-PUOUXSMHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C14H17NO9
Molecular Weight 343.29 g/mol
Exact Mass 343.09033112 g/mol
Topological Polar Surface Area (TPSA) 158.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -2.13
H-Bond Acceptor 9
H-Bond Donor 6
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-6-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-1,4-benzoxazin-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5757 57.57%
Caco-2 - 0.8094 80.94%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.4068 40.68%
OATP2B1 inhibitior - 0.8566 85.66%
OATP1B1 inhibitior + 0.8892 88.92%
OATP1B3 inhibitior + 0.9399 93.99%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.8722 87.22%
P-glycoprotein inhibitior - 0.9107 91.07%
P-glycoprotein substrate - 0.8860 88.60%
CYP3A4 substrate + 0.5581 55.81%
CYP2C9 substrate - 0.8052 80.52%
CYP2D6 substrate - 0.8487 84.87%
CYP3A4 inhibition - 0.9425 94.25%
CYP2C9 inhibition - 0.8540 85.40%
CYP2C19 inhibition - 0.8091 80.91%
CYP2D6 inhibition - 0.9275 92.75%
CYP1A2 inhibition - 0.7028 70.28%
CYP2C8 inhibition + 0.4458 44.58%
CYP inhibitory promiscuity - 0.7941 79.41%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7066 70.66%
Eye corrosion - 0.9929 99.29%
Eye irritation - 0.8876 88.76%
Skin irritation - 0.8224 82.24%
Skin corrosion - 0.9622 96.22%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4835 48.35%
Micronuclear + 0.8400 84.00%
Hepatotoxicity - 0.8049 80.49%
skin sensitisation - 0.8581 85.81%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity - 0.6434 64.34%
Acute Oral Toxicity (c) III 0.6645 66.45%
Estrogen receptor binding + 0.6166 61.66%
Androgen receptor binding + 0.6371 63.71%
Thyroid receptor binding + 0.5403 54.03%
Glucocorticoid receptor binding + 0.6089 60.89%
Aromatase binding - 0.5057 50.57%
PPAR gamma + 0.5542 55.42%
Honey bee toxicity - 0.8075 80.75%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5850 58.50%
Fish aquatic toxicity - 0.7543 75.43%

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 98.11% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.55% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.46% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.39% 85.14%
CHEMBL2581 P07339 Cathepsin D 91.56% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.13% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.31% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.80% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.94% 95.56%
CHEMBL1937 Q92769 Histone deacetylase 2 85.59% 94.75%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.23% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 83.63% 94.73%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 83.26% 89.67%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.53% 86.33%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.82% 95.83%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.88% 99.17%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.55% 94.80%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.11% 95.89%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 80.05% 99.15%

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.
Curcuma comosa
Lamium galeobdolon

Cross-Links

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PubChem 641761
LOTUS LTS0106541
wikiData Q104914472