Molecule

Validoxylamine A

AlkaPlorer ID: AK023200

Synonym: None

IUPAC Name: (1S,2S,3R,6S)-4-(hydroxymethyl)-6-[[(1S,2S,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]amino]cyclohex-4-ene-1,2,3-triol

Structure

SMILES: OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI: InChI=1S/C14H25NO8/c16-3-5-1-7(11(20)13(22)9(5)18)15-8-2-6(4-17)10(19)14(23)12(8)21/h1,6-23H,2-4H2/t6-,7+,8+,9-,10-,11+,12+,13+,14+/m1/s1

InChIKey: YCJYNBLLJHFIIW-MBABXGOBSA-N

Reference

Preparation of Trehalase Inhibitor Validoxylamine A by Biocatalyzed Hydrolysis of Validamycin A With Honeybee (<I>Apis cerana</I> Fabr.) β-Glucosidase

PubChem CID: 11450478

CAS: 38665-10-0

LOTUS: LTS0009543

NPASS: NPC319537

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces hygroscopicus	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria
Apis cerana	Apis	Apidae	Hymenoptera	Insecta	Arthropoda	Metazoa	Eukaryota

Properties Information

Molecule Weight: 335.353

TPSA？: 173.86999999999998

MolLogP？: -4.576899999999995

Number of H-Donors: 9

Number of H-Acceptors: 9

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bombyx mori	Trehalase	IC50	48.0	nM	10.1584/jpestics.19.39
Bombyx mori	Trehalase	Inhibition	78.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	0.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	7.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	10.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	13.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	20.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	27.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	40.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	60.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	80.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	90.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	Activity	100.0	%	10.1584/jpestics.19.39
Mamestra brassicae	Mamestra brassicae	LD50	1.0	ug	10.1584/jpestics.19.39
Rattus norvegicus	Trehalase	IC50	4.9	nM	10.1584/jpestics.19.39
Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)	Vacuolar acid trehalase	IC50	3.0	nM	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	0.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	5.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	10.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	13.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	15.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	20.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	25.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	30.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	40.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	58.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	60.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	Activity	85.0	%	10.1584/jpestics.19.39
Spodoptera litura	Spodoptera litura	LD50	2.42	ug	10.1584/jpestics.19.39
Thanatephorus cucumeris (strain AG1-IB / isolate 7/3/14) (Lettucebottom rot fungus) (Rhizoctonia solani)	Chitinase A1	IC50	1000000.0	nM	10.1584/jpestics.19.39
None	Unchecked	IC50	1000000.0	nM	10.1584/jpestics.19.39

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT015225	Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)c(=O)[nH]c1=O.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	enzymemap_36881
AKRT016611	N=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)c2[nH]1.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	enzymemap_36880
AKRT021527	Nc1nc2c(ncn2[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.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	enzymemap_36880
AKRT022162	Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	enzymemap_36879
AKRT023821	O=P(O)(O)OC[C@H]1C[C@H](N[C@H]2C=C(CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	RXN-17380
AKRT024587	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.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	None
AKRT024588	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.OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	RXN-9148
AKRT024805	OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C1C=C(COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H]1O	MNXR177421
AKRT024806	OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C1C[C@H](COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H]1O	MNXR177421
AKRT024807	OCC1=C[C@H](N[C@H]2C[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>OCC1=C[C@H](N[C@@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	55648