Molecule

SF-733

AlkaPlorer ID: AK013078

Synonym: None

IUPAC Name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol

Structure

SMILES: NC[C@H]1O[C@H](O[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O

InChI: InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1

InChIKey: NSKGQURZWSPSBC-VVPCINPTSA-N

Reference

Cloning and analysis of a gene (SMS13) encoding sannamycin B-glycyltransferase from Streptomyces sannanensis and its distribution among actinomycetes.

PubChem CID: 33042

CAS: 25546-65-0

LOTUS: LTS0231220

SuperNatural Ⅲ: SN0254014-06

{

NPAtlas: NPA024702

Source

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

Properties Information

Molecule Weight: 454.47700000000015

TPSA？: 262.38000000000005

MolLogP？: -6.6523

Number of H-Donors: 10

Number of H-Acceptors: 14

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Acinetobacter baumannii	Acinetobacter baumannii	MIC	8.0	ug.mL-1	10.1039/C5MD00429B
Acinetobacter baumannii	Acinetobacter baumannii	MIC	16.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Acinetobacter baumannii	Acinetobacter baumannii	MIC	64.0	ug.mL-1	10.1039/C5MD00429B
Burkholderia cepacia	Burkholderia cepacia	MIC	32.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Enterobacter cloacae	Enterobacter cloacae	MIC	64.0	ug.mL-1	10.1039/C5MD00429B
Escherichia coli	Escherichia coli	MIC	0.25	ug.mL-1	10.1128/aac.00926-07
Escherichia coli	Escherichia coli	MIC	0.5	ug.mL-1	10.1128/aac.00926-07
Escherichia coli	Escherichia coli	MIC	4.0	ug.mL-1	10.1016/j.bmc.2007.08.059
Escherichia coli	Escherichia coli	MIC	4.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Escherichia coli	Escherichia coli	MIC	8.0	ug.mL-1	10.1016/j.bmc.2007.08.059
Escherichia coli	Escherichia coli	MIC	8.0	ug.mL-1	10.1039/C5MD00429B
Escherichia coli	Escherichia coli	MIC	12.0	ug.mL-1	10.1128/aac.01034-06
Escherichia coli	Escherichia coli	MIC	32.0	ug.mL-1	10.1016/j.bmc.2007.08.059
Escherichia coli	Escherichia coli	MIC	32.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Escherichia coli	Escherichia coli	MIC	64.0	ug.mL-1	10.1039/C5MD00429B
Escherichia coli	Escherichia coli	MIC	256.0	ug.mL-1	10.1128/aac.00926-07
Escherichia coli	Escherichia coli	MIC	768.0	ug.mL-1	10.1128/aac.01034-06
Haemophilus influenzae	Haemophilus influenzae	MIC	8.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Homo sapiens	Histone deacetylase 6	Inhibition	-5.95	%	10.6019/CHEMBL4808148
Homo sapiens	Histone deacetylase 6	Inhibition	-3.61	%	10.6019/CHEMBL4808148
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	2.0	ug.mL-1	10.1039/C5MD00429B
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	8.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	32.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Nocardia farcinica	Nocardia farcinica	MIC	256.0	ug.mL-1	10.1128/aac.00021-10
Nocardia farcinica	Nocardia farcinica	MIC	1024.0	ug.mL-1	10.1128/aac.00021-10
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	32.0	ug.mL-1	10.1021/acs.jmedchem.6b00793
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	64.0	ug.mL-1	10.1039/C5MD00429B
Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	384.0	ug.mL-1	10.1128/aac.01034-06
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Aminoglycoside 3'-phosphotransferase type IIb	Kcat/Km	190000.0	/M/s	10.1128/aac.01034-06
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Aminoglycoside 3'-phosphotransferase type IIb	Km	10000.0	nM	10.1128/aac.01034-06
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	19952.62	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	20000.0	nM	10.6019/CHEMBL4651402
Staphylococcus aureus	Staphylococcus aureus	MIC	8.0	ug.mL-1	10.1021/ml200202y
Staphylococcus aureus	Staphylococcus aureus	MIC	16.0	ug.mL-1	10.1039/C5MD00429B
Staphylococcus aureus	Staphylococcus aureus	MIC	64.0	ug.mL-1	10.1021/ml200202y
Staphylococcus aureus	Staphylococcus aureus	MIC	64.0	ug.mL-1	10.1039/C5MD00429B
None	ADMET	C50	1.2	uM	10.1021/jm00385a015
None	ADMET	CL	1.5	mL.min-1.kg-1	10.1124/dmd.108.020479
None	ADMET	Kill at C50	99.0	%	10.1021/jm00385a015
None	ADMET	LD90	0.17	uM	10.1021/jm00385a015
None	ADMET	MRT	2.8	hr	10.1124/dmd.108.020479
None	ADMET	T1/2	2.5	hr	10.1124/dmd.108.020479
None	ADMET	Uptake at C50	2.6	None	10.1021/jm00385a015
None	ADMET	Vdss	0.25	L.kg-1	10.1124/dmd.108.020479
None	Nucleic Acid	Activity	nan	None	10.1128/aac.00926-07
None	Nucleic Acid	Kd	1700.0	nM	10.1021/jm9000659
None	Nucleic Acid	MIC	100000.0	nM	10.1021/jm970372r
None	Ribosomal RNA A-site	IC50	90.0	nM	10.1021/acs.jmedchem.6b00793
None	Ribosomal RNA A-site	Kd	16350.0	nM	10.1021/jm060288o
None	Ribosomal RNA A-site	Kd	25000.0	nM	10.1016/s0960-894x(00)00615-6
None	Unchecked	Activity	nan	None	10.1039/C5MD00496A
None	Unchecked	IC50	115810.0	nM	10.1021/acs.jmedchem.6b00793
None	Unchecked	Ratio IC50	1286.78	None	10.1021/acs.jmedchem.6b00793

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT001015	*SC(=O)[C@@H](O)CCNC(=O)CC[C@H](N)C(=O)O.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](NC(=O)[C@@H](O)CCNC(=O)CC[C@H](N)C(=O)O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)C1O	RXN-13217
AKRT001016	*SC(=O)[C@@H](O)CCNC(=O)CC[C@H](N)C(=O)O.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](NC(=O)[C@@H](O)CCNC(=O)CC[C@H](N)C(=O)O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O	R08909
AKRT003531	CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O	RXN-13176
AKRT003532	CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O.NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O	enzymemap_36552
AKRT004428	CC(=O)[32S].NC[C@H]1O[C@H](O[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)NC[C@H]1O[C@H](O[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O	None
AKRT004429	CC(=O)[32S].NC[C@H]1O[C@H](O[C@H]2[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@@H]1O[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1N	None
AKRT004668	CC(=O)[CoA].NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O	enzymemap_32280
AKRT004669	CC(=O)[CoA].NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@@H]1O[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1N	enzymemap_32221
AKRT004670	CC(=O)[CoA].NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)O[C@H](CN)[C@@H](O)[C@@H]1O	enzymemap_31521
AKRT018496	NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)C(=O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O	R11265
AKRT018497	NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)C(=O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O	R11265
AKRT018499	NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O>>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)[C@H](N)[C@@H](O)[C@@H]1O	RXN-13204