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(2R)-DIMBOA glucoside

AlkaPlorer ID: AK020442

Synonym: '', 'DIMBOA beta-D-glucoside', '2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside', '2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside', '(2R)-2-beta-D-Glucopyranosyloxy-4-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one', 'DIMBOA glucoside'

IUPAC Name: (2R)-4-hydroxy-7-methoxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4-benzoxazin-3-one

Structure

SMILES: COC1=CC=C2C(=C1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O

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InChI: InChI=1S/C15H19NO10/c1-23-6-2-3-7-8(4-6)24-15(13(21)16(7)22)26-14-12(20)11(19)10(18)9(5-17)25-14/h2-4,9-12,14-15,17-20,22H,5H2,1H3/t9-,10-,11+,12-,14+,15-/m1/s1

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InChIKey: WTGXAWKVZMQEDA-XFWGRBSCSA-N

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Reference

PubChem CID: 441563

SuperNatural Ⅲ: SN0419441-05

NPASS: NPC290069

Source

Species Genus Family Order Class Phylum Kingdom Domain
None Coix Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 373.3140000000001

TPSA？: 158.38000000000002

MolLogP？: -2.0475999999999988

Number of H-Donors: 5

Number of H-Acceptors: 10

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Mus musculus Mast cell Inhibition 3.0 % 10.1021/np50055a009
Mus musculus Mast cell Inhibition nan % 10.1021/np50055a009

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011867 COc1ccc2c(c1)OC(O)C(=O)N2O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O enzymemap_35650
AKRT011868 COc1ccc2c(c1)OC(O)C(=O)N2O.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O MNXR131760
AKRT011872 COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O>>COc1ccc2c(c1)OC(O)C(=O)N2O enzymemap_60274
AKRT011873 COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O>>COc1ccc2c(c1)OC(O)C(=O)N2O.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O None
AKRT011874 COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O>>COc1ccc2c(c1)O[C@@H](O)C(=O)N2O enzymemap_60262
AKRT011875 COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O>>OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O enzymemap_60262
AKRT011876 COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O>>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O enzymemap_60274
AKRT014734 C[SAH].O=C1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2cc(O)ccc2N1O>>COc1ccc2c(c1)O[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2O R08973