Summary

IMPPAT Phytochemical identifier: IMPHY000095

Phytochemical name: DIMBOA glucoside

Synonymous chemical names:
(2r)-β-d-glucopyranosyloxy-4-hydroxy-7-methoxy-2h-1,4-benzoxazin-3(4h)-one, 2-(2,4-dihydroxy-1,4(2h)-benzoxazin-3(4h)-on-beta-d-glucoside, 2-(2,4-dihydroxy-7-methoxy-1-4(2h)-benzoxazin-3-(4h)on)-beta-d-glucoside, 2-(2-hydroxy-4,7-dimethoxy-1-4(2h)-benzoxazin-3-one-beta-d-glucoside, 2-(2-hydroxy-7-methoxy-1,4(2h)-benzoxazin-3(4h)-on-beta-d-glucoside

External chemical identifiers:
CID:441563, ChEMBL:CHEMBL519905, ChEBI:37573

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Chemical structure information

SMILES:
OC[C@H]1O[C@@H](O[C@H]2Oc3cc(OC)ccc3N(C2=O)O)[C@@H]([C@H]([C@@H]1O)O)O

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

InChIKey:
WTGXAWKVZMQEDA-XFWGRBSCSA-N

DeepSMILES:
OC[C@H]O[C@@H]O[C@H]OcccOC))ccc6NC%10=O))O)))))))))))[C@@H][C@H][C@@H]6O))O))O

Functional groups:
CO, CO[C@H](C)O[C@H]1OccN(O)C1=O, cOC

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1Nc2ccccc2OC1OC1CCCCO1

Scaffold Graph/Node level:
OC1NC2CCCCC2OC1OC1CCCCO1

Scaffold Graph level:
CC1CC2CCCCC2CC1CC1CCCCC1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Organic oxygen compounds

ClassyFire Class: Organooxygen compounds

ClassyFire Subclass: Carbohydrates and carbohydrate conjugates

NP Classifier Biosynthetic pathway: Alkaloids

NP-Likeness score: 1.55

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Chemical structure download