NP-MRD: Showing NP-Card for paromomycin (NP0229356)

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Record Information

Version

2.0

Created at

2022-09-06 09:22:37 UTC

Updated at

2022-09-06 09:22:37 UTC

NP-MRD ID

NP0229356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paromomycin

Description

Paromomycin, also known as aminosidin or crestomycin, belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions. Paromomycin is a drug which is used for the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy. It is also used as a therapeutic against visceral leishmaniasis. Paromomycin is a very strong basic compound (based on its pKa). In humans, paromomycin is involved in paromomycin action pathway. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. An amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). paromomycin is found in Streptomyces fradiae. paromomycin was first documented in 1994 (PMID: 8036682). It is obtained from various Streptomyces species (PMID: 11587639) (PMID: 18447603) (PMID: 18947845).

Structure

MOL 3D MOL SDF PDB SMILES InChI

1421
  Mrv0541 02231215292D          

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M  END

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M  END

1421
  Mrv0541 02231215292D          

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    3.1434   -3.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5078   -3.1377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -2.8358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808    0.2432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2493    3.3049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0095    0.7213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349   -1.1857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9203   -1.5982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9203   -2.4232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3493   -1.5982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3493   -2.4232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6349   -2.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3493    0.0518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2426    1.0438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4356    0.8723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6551    0.3293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3808   -1.1857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9684   -0.4712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1433   -0.4712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3986    1.8838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7308   -1.1857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7341    2.6375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1433   -1.9002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5547    2.7237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4756    0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0397    2.0563    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7040    1.3025    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7308   -2.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1890    0.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20  1  1  6  0  0  0
 26  1  1  1  0  0  0
 21  2  1  1  0  0  0
 30  2  1  1  0  0  0
  3 26  1  0  0  0  0
  3 29  1  0  0  0  0
 27  4  1  6  0  0  0
 33  4  1  6  0  0  0
 23  5  1  1  0  0  0
  6 30  1  0  0  0  0
  6 36  1  0  0  0  0
  7 33  1  0  0  0  0
  7 40  1  0  0  0  0
 28  8  1  6  0  0  0
 32  9  1  6  0  0  0
 34 10  1  1  0  0  0
 37 11  1  1  0  0  0
 12 38  1  0  0  0  0
 39 13  1  6  0  0  0
 14 41  1  0  0  0  0
 22 15  1  6  0  0  0
 24 16  1  6  0  0  0
 31 17  1  1  0  0  0
 35 18  1  6  0  0  0
 19 42  1  0  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 38  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 34  1  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  1  0  0  0  0
 36 41  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0229356

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

> <INCHI_KEY>
UOZODPSAJZTQNH-LSWIJEOBSA-N

> <FORMULA>
C23H45N5O14

> <MOLECULAR_WEIGHT>
615.6285

> <EXACT_MASS>
615.296301173

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
60.40275856764997

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

> <ALOGPS_LOGP>
-2.92

> <JCHEM_LOGP>
-8.308295949333333

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
5

> <JCHEM_PKA>
12.902517812527407

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.227454691752135

> <JCHEM_PKA_STRONGEST_BASIC>
9.938207381101218

> <JCHEM_POLAR_SURFACE_AREA>
347.31999999999994

> <JCHEM_REFRACTIVITY>
134.2427999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paromomycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1421                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.385  -0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.718  -2.213   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.126  -0.530   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.012   3.355   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.052  -2.213   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.407  -3.547   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.449   2.270   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.735   2.659   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.098   0.454   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.557  -2.213   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      20.328   6.491   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      18.314  -0.953   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      22.139   3.999   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.868  -6.215   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      10.281  -5.857   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      15.052  -5.293   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       8.177   0.454   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      17.265   6.169   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      22.418   1.346   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      12.385  -2.213   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.051  -2.983   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.051  -4.523   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.719  -2.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.719  -4.523   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.385  -5.293   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.719   0.097   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.386   1.948   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.880   1.628   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.156   0.615   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.177  -2.213   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.408  -0.880   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.867  -0.880   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.544   3.516   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.097  -2.213   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.170   4.923   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.867  -3.547   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      19.702   5.084   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.688   0.454   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.607   3.838   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.981   2.431   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.097  -4.881   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      20.886   1.186   0.000  0.00  0.00           C+0
CONECT    1   20   26                                                       
CONECT    2   21   30                                                       
CONECT    3   26   29                                                       
CONECT    4   27   33                                                       
CONECT    5   23                                                            
CONECT    6   30   36                                                       
CONECT    7   33   40                                                       
CONECT    8   28                                                            
CONECT    9   32                                                            
CONECT   10   34                                                            
CONECT   11   37                                                            
CONECT   12   38                                                            
CONECT   13   39                                                            
CONECT   14   41                                                            
CONECT   15   22                                                            
CONECT   16   24                                                            
CONECT   17   31                                                            
CONECT   18   35                                                            
CONECT   19   42                                                            
CONECT   20    1   21   23                                                  
CONECT   21    2   20   22                                                  
CONECT   22   15   21   25                                                  
CONECT   23    5   20   24                                                  
CONECT   24   16   23   25                                                  
CONECT   25   22   24                                                       
CONECT   26    1    3   28                                                  
CONECT   27    4   28   29                                                  
CONECT   28    8   26   27                                                  
CONECT   29    3   27   38                                                  
CONECT   30    2    6   31                                                  
CONECT   31   17   30   32                                                  
CONECT   32    9   31   34                                                  
CONECT   33    4    7   35                                                  
CONECT   34   10   32   36                                                  
CONECT   35   18   33   37                                                  
CONECT   36    6   34   41                                                  
CONECT   37   11   35   39                                                  
CONECT   38   12   29                                                       
CONECT   39   13   37   40                                                  
CONECT   40    7   39   42                                                  
CONECT   41   14   36                                                       
CONECT   42   19   40                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside	ChEBI
Aminosidin	ChEBI
Aminosidine	ChEBI
Catenulin	ChEBI
Crestomycin	ChEBI
Estomycin	ChEBI
Hydroxymycin	ChEBI
Monomycin a	ChEBI
Neomycin e	ChEBI
Paromomicina	ChEBI
Paromomycin I	ChEBI
Paromomycine	ChEBI
Paromomycinum	ChEBI
Paucimycin	ChEBI
Paucimycinum	ChEBI
R 400	ChEBI
R-400	ChEBI
Zygomycin a1	ChEBI
PRM	Kegg
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-b-L-idopyranosyl)-b-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-a-D-glucopyranoside	Generator
(1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-β-L-idopyranosyl)-β-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-α-D-glucopyranoside	Generator
Paramomycin sulfate	HMDB
Paramomycin sulphate	HMDB
Gabbromycin	HMDB
Parke davis brand OF paromomycin sulfate	HMDB
Paromomycin, beta-D-glucopyranosyl-isomer	HMDB
Sulfate, paromomycin	HMDB
Humatin	HMDB
Phosphate, paromomycin	HMDB
Cheminova brand OF paromomycin sulfate	HMDB
Paromomycin sulfate (1:1)	HMDB
Pfizer brand OF paromomycin sulfate	HMDB
beta-D-Glucopyranosyl-isomer paromomycin	HMDB
Monarch brand OF paromomycin sulfate	HMDB
Paramomycin	HMDB
Paromomycin phosphate	HMDB
Paromomycin sulfate	HMDB
Paromomycin sulfate (2:5)	HMDB
Paromomycin, beta D glucopyranosyl isomer	HMDB

Chemical Formula

C₂₃H₄₅N₅O₁₄

Average Mass

615.6285 Da

Monoisotopic Mass

615.29630 Da

IUPAC Name

(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol

Traditional Name

paromomycin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

InChI Key

UOZODPSAJZTQNH-LSWIJEOBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

4,5-disubstituted 2-deoxystreptamines

Alternative Parents

Substituents

4,5-disubstituted 2-deoxystreptamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
1,2-aminoalcohol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organopnictogen compound
Primary aliphatic amine
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

aminoglycoside antibiotic (CHEBI:7934 )
amino cyclitol glycoside (CHEBI:7934 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.9	ALOGPS
logP	-8.3	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	12.23	ChemAxon
pKa (Strongest Basic)	9.94	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	347.32 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	134.24 m³·mol⁻¹	ChemAxon
Polarizability	60.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0015490

DrugBank ID

DB01421

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

145115

KEGG Compound ID

C00832

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paromomycin

METLIN ID

Not Available

PubChem Compound

165580

PDB ID

PAR

ChEBI ID

7934

Good Scents ID

Not Available

References

General References

Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58. doi: 10.1016/s0969-2126(01)00629-3. [PubMed:11587639 ]
Sundar S, Chakravarty J: Paromomycin in the treatment of leishmaniasis. Expert Opin Investig Drugs. 2008 May;17(5):787-94. doi: 10.1517/13543784.17.5.787. [PubMed:18447603 ]
Davidson RN, den Boer M, Ritmeijer K: Paromomycin. Trans R Soc Trop Med Hyg. 2009 Jul;103(7):653-60. doi: 10.1016/j.trstmh.2008.09.008. Epub 2008 Oct 23. [PubMed:18947845 ]
Neal RA, Murphy AG, Olliaro P, Croft SL: Aminosidine ointments for the treatment of experimental cutaneous leishmaniasis. Trans R Soc Trop Med Hyg. 1994 Mar-Apr;88(2):223-5. doi: 10.1016/0035-9203(94)90307-7. [PubMed:8036682 ]
LOTUS database [Link]

Showing NP-Card for paromomycin (NP0229356)

MOL for NP0229356 (paromomycin)

3D MOL for NP0229356 (paromomycin)

3D SDF for NP0229356 (paromomycin)

3D-SDF for NP0229356 (paromomycin)

PDB for NP0229356 (paromomycin)

3D PDB for NP0229356 (paromomycin)

SMILES for NP0229356 (paromomycin)

INCHI for NP0229356 (paromomycin)

Structure for NP0229356 (paromomycin)

3D Structure for NP0229356 (paromomycin)