ContaminantDB: Amikacin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:37:03 UTC

Update Date

2016-11-09 01:15:25 UTC

Accession Number

CHEM016560

Identification

Common Name

Amikacin

Class

Small Molecule

Description

An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-N-(L(-)-gamma-Amino-alpha-hydroxybutyryl)kanamycin a	ChEBI
Amicacin	ChEBI
Amiglyde-V	ChEBI
Amikacina	ChEBI
Amikacine	ChEBI
Amikacinum	ChEBI
Amikavet	ChEBI
Briclin	ChEBI
O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine	ChEBI
1-N-(L(-)-g-Amino-a-hydroxybutyryl)kanamycin a	Generator
1-N-(L(-)-Γ-amino-α-hydroxybutyryl)kanamycin a	Generator
O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-a-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine	Generator
O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-α-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine	Generator
AMK	HMDB
Amikacin base	HMDB
Amikacin dihydrate	HMDB
Amikacin sulfate	HMDB
ANTIBIOTIC BB-K8	HMDB
BB-K8	HMDB
A.M.K	HMDB
Amikacina normon	HMDB
Amikafur	HMDB
Amikason's	HMDB
Amikin	HMDB
Bristol myers squibb brand OF amikacin sulfate	HMDB
Bristol-myers squibb brand OF amikacin sulfate	HMDB
Collins brand OF amikacin sulfate	HMDB
Fustery brand OF amikacin sulfate	HMDB
Galen brand OF amikacin sulfate	HMDB
Gamikal	HMDB
Medical, amikacina	HMDB
Normon, amikacina	HMDB
Son's brand OF amikacin sulfate	HMDB
Sulfate, amikacin	HMDB
Amikacina medical	HMDB
Amikalem	HMDB
Amiklin	HMDB
Apothecon brand OF amikacin sulfate	HMDB
BB K 8	HMDB
BB-K 8	HMDB
BBK 8	HMDB
Norman brand OF amikacin sulfate	HMDB
Amikayect	HMDB
Amukin	HMDB
BBK8	HMDB
Biclin	HMDB
Biklin	HMDB
Cryopharma brand OF amikacin sulfate	HMDB
Grossmann brand OF amikacin sulfate	HMDB
Kanbine	HMDB
Lemery brand OF amikacin sulfate	HMDB
Mead johnson brand OF amikacin sulfate	HMDB
Yectamid	HMDB
BB K8	HMDB
Medical brand OF amikacin sulfate	HMDB
Oprad	HMDB
Pisa brand OF amikacin sulfate	HMDB
Rovi brand OF amikacin sulfate	HMDB

Chemical Formula

C₂₂H₄₃N₅O₁₃

Average Molecular Mass

585.603 g/mol

Monoisotopic Mass

585.286 g/mol

CAS Registry Number

37517-28-5

IUPAC Name

(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide

Traditional Name

amikacin

SMILES

NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O

InChI Identifier

InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1

InChI Key

LKCWBDHBTVXHDL-RMDFUYIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

4,6-disubstituted 2-deoxystreptamines

Alternative Parents

Substituents

4,6-disubstituted 2-deoxystreptamine
Gamma amino acid or derivatives
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Fatty acyl
Monosaccharide
N-acyl-amine
Cyclitol or derivatives
Fatty amide
Oxane
1,3-aminoalcohol
Cyclic alcohol
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Amino acid or derivatives
1,2-aminoalcohol
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Carbonyl group
Primary alcohol
Primary amine
Hydrocarbon derivative
Amine
Alcohol
Organic oxide
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

alpha-D-glucoside (CHEBI:2637 )
aminoglycoside (CHEBI:2637 )
carboxamide (CHEBI:2637 )
amino cyclitol glycoside (CHEBI:2637 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	49.7 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-8.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	331.94 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	129.84 m³·mol⁻¹	ChemAxon
Polarizability	58.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0hh9-9803480000-4e62c20842f82ac0dc88	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9400112000-f033c515f4f33f591c6d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Amikacin,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0arr-0012930000-e9e5c2d0a10606a482a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fr-1172910000-aa60237b3c5b04a8a3e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03k9-4589400000-6018610d9123baec32bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0089-3804890000-fcfb985392039be545de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-7323930000-388eeb644330ca9e4545	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0229-9787300000-fe9d1c5ff399b6290a43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0100290000-b042b8a83e28d8bdf7af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-0341910000-4cd2607184ac898dc72d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9801200000-d277a1c07ae9c5013c40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0100290000-ce68b38055d76811ba9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05o0-4103930000-0d2c17d64e8e87154ca1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05gi-7029300000-6576f3b613f9854d5ffd	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum