Molecule

Validamycin

AlkaPlorer ID: AK012008

Synonym: None

IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Structure

SMILES: 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

InChI: InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1

InChIKey: JARYYMUOCXVXNK-CSLFJTBJSA-N

Reference

Genetic localization and heterologous expression of validamycin biosynthetic gene cluster isolated from Streptomyces hygroscopicus var. limoneus KCCM 11405 (IFO 12704)

PubChem CID: 443629

LOTUS: LTS0123861

SuperNatural Ⅲ: SN0160393-08

NPASS: NPC20035

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Streptomyces hygroscopicus	Streptomyces	Streptomycetaceae	Kitasatosporales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 497.494

TPSA？: 253.01999999999995

MolLogP？: -6.752699999999988

Number of H-Donors: 12

Number of H-Acceptors: 14

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Cercospora beticola	Cercospora beticola	Inhibition	42.0	%	10.1016/j.ejmech.2013.04.014
Corticium	Corticium	Efficacy	75.0	%	10.1021/jf900674y
Corticium	Corticium	Efficacy	100.0	%	10.1021/jf900674y
Fusarium oxysporum	Fusarium oxysporum	Inhibition	35.0	%	10.1016/j.ejmech.2013.04.014
Rhizoctonia solani	Rhizoctonia solani	Activity	70.0	%	10.1021/jf203017f
Rhizoctonia solani	Rhizoctonia solani	Activity	100.0	%	10.1021/jf203017f
Rhizoctonia solani	Rhizoctonia solani	EC50	0.08	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	0.09	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	0.1	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	0.14	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	0.16	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	0.18	ug.mL-1	10.1016/j.cropro.2008.12.004
Rhizoctonia solani	Rhizoctonia solani	EC50	197.6	ug.mL-1	10.1016/j.ejmech.2021.114057
Rhizoctonia solani	Rhizoctonia solani	Efficacy	93.68	%	10.1021/jf303807a
Rhizoctonia solani	Rhizoctonia solani	GI	5.7	%	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	GI	17.0	%	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	GI	22.6	%	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	GI	34.0	%	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	GI	45.2	%	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	GI	80.96	%	10.1016/j.bmcl.2011.09.068
Rhizoctonia solani	Rhizoctonia solani	GI	nan	None	10.1016/j.cropro.2006.09.014
Rhizoctonia solani	Rhizoctonia solani	Inhibition	75.0	%	10.1016/j.ejmech.2013.04.014
None	Molecular identity unknown	Inhibition	37.0	%	10.1016/j.ejmech.2013.04.014
None	Molecular identity unknown	Inhibition	47.0	%	10.1016/j.ejmech.2013.04.014

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
AKRT022734	O=C(O)CCC(=O)C(=O)O.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>>O=C(O)CCC(=O)O.O=C=O.OCC1=C[C@H](N[C@@H]2[C@H](O)[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](CO)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	None
AKRT022735	O=C(O)CCC(=O)C(=O)O.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>>O=C(O)CCC(=O)O.O=C=O.OCC1=C[C@H](N[C@@H]2[C@H](O)[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](CO)[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
AKRT024808	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>>OCC1=C[C@H](N[C@@H]2[C@H](O)[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](CO)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O	RXN-17381
AKRT024809	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>>OCC1=C[C@H](N[C@H]2[C@@H](O)[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_10931