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name Structure Reference Source Properties Activities Metabolism

2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one; (R)-form, N-Hydroxy 

AlkaPlorer ID: AK300862

Synonym: 2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one, DIBOA 

IUPAC Name: 2,4-dihydroxy-1,4-benzoxazin-3-one

Structure

SMILES: O=C1C(O)OC2=C(C=CC=C2)N1O

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InChI: InChI=1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H

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InChIKey: COVOPZQGJGUPEY-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Acanthus ilicifolius Acanthus Acanthaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 181.147

TPSA？: 70.0

MolLogP？: 0.1195999999999999

Number of H-Donors: 2

Number of H-Acceptors: 4

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Abutilon theophrasti Abutilon theophrasti Activity 0.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 6.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 40.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 59.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 72.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 82.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity 97.0 % 10.1021/np50037a010
Abutilon theophrasti Abutilon theophrasti Activity nan None 10.1021/np50037a010
Candida albicans Candida albicans MIC 3676600.0 nM 10.1016/j.bmc.2018.11.016
Escherichia coli Escherichia coli MIC 6900500.0 nM 10.1016/j.bmc.2018.11.016
Rhopalosiphum padi Rhopalosiphum padi Activity 92.3 % 10.1021/jf030766t
Staphylococcus aureus Staphylococcus aureus MIC 2760200.0 nM 10.1016/j.bmc.2018.11.016

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT023494 O=C1C(O)Oc2cc(O)ccc2N1O>>O=C1C(O)Oc2ccccc2N1O MNXR179482
AKRT023495 O=C1C(O)Oc2ccccc2N1O.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>>O=C1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O RXN-7021
AKRT023496 O=C1C(O)Oc2ccccc2N1O.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>>O=C1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O R07426
AKRT023497 O=C1C(O)Oc2ccccc2N1O.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O MNXR172045
AKRT023498 O=C1C(O)Oc2ccccc2N1O>>O=C1Nc2ccccc2OC1O enzymemap_13009
AKRT023499 O=C1C(O)Oc2ccccc2N1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>O=C1C(O)Oc2ccccc2N1O enzymemap_61111
AKRT023500 O=C1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O>>O=C1C(O)Oc2ccccc2N1O RXN-13137
AKRT023621 O=C1Nc2ccccc2OC1O>>O=C1C(O)Oc2ccccc2N1O RXN-6684
AKRT023629 O=C1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O>>O=C1C(O)Oc2ccccc2N1O enzymemap_60264
AKRT023630 O=C1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)Oc2ccccc2N1O>>O=C1C(O)Oc2ccccc2N1O.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O None