Marvin  04061111592D          

 39 42  0  0  1  0            999 V2000
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    4.9920   -8.5307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6933   -8.9432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4359   -8.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359   -7.7057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6933   -7.2932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9920   -7.7057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6933   -9.7683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -7.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1372   -7.2932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6933   -6.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3946   -6.0556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0959   -6.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8384   -6.0556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8384   -5.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1372   -4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3946   -5.2305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6933   -4.8180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5397   -6.4681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2410   -6.0556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2410   -5.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5397   -4.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9423   -4.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9423   -6.4681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5397   -7.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6436   -6.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6436   -3.5805    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6436   -4.4055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3449   -4.8180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0874   -4.4055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0874   -3.5805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3449   -3.1679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9423   -3.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7887   -3.1679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -2.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7887   -4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4900   -4.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8384   -6.7569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8384   -4.4055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  1  0  0  0
  7  9  1  1  0  0  0
  5 10  1  1  0  0  0
  6 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  6  0  0  0
 20 24  1  1  0  0  0
 19 25  1  1  0  0  0
 24 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 28 23  1  6  0  0  0
 27 33  1  6  0  0  0
 31 34  1  6  0  0  0
 32 35  1  1  0  0  0
 30 36  1  1  0  0  0
 36 37  1  0  0  0  0
 14 38  1  6  0  0  0
 15 39  1  1  0  0  0
M  END
> <ID>
CHEBI:2790

> <NAME>
apramycin

> <DEFINITION>
An aminoglycoside that is 2-deoxystreptamine that is substituted on the oxygen at position 4 by an (8R)-2-amino-8-O-(4-amino-4-deoxy-?-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-?-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl) group.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:40708

> <SYNONYM>
nebramycin II; nebramycin factor 2; Apramycin; APRAMYCIN; 4-O-(3alpha-amino-6alpha-((4-amino-4-deoxy-alpha-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-D-streptamine; 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine

> <IUPAC_NAME>
(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl 4-amino-4-deoxy-alpha-D-glucopyranoside

> <INN>
apramycinum; apramycine; apramycin; apramicina

> <FORMULA>
C21H41N5O11

> <MASS>
539.57710

> <MONOISOTOPIC_MASS>
539.28026

> <CHARGE>
0

> <SMILES>
[H][C@]12C[C@@H](N)[C@@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@]1([H])[C@H](O)[C@H](NC)[C@@H](O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O)O2

> <INCHI>
InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

> <INCHIKEY>
XZNUGFQTQHRASN-XQENGBIVSA-N

> <CAS_REGISTRY_NUMBER>
37321-09-8

> <REAXYS_REGISTRY_NUMBER>
4610404

> <CHEMIDPLUS>
37321-09-8

> <DRUGBANK_ACCESSION>
DB04626

> <KEGG_COMPOUND_ACCESSION>
C01555

> <KEGG_DRUG_ACCESSION>
D02322

> <PDBECHEM_ACCESSION>
AM2

> <PUBMED_CITATION>
1249675; 340441; 690031; 932851

$$$$