NP-MRD: Showing NP-Card for Apramycin (NP0023538)

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Record Information

Version

1.0

Created at

2021-01-06 08:36:33 UTC

Updated at

2021-07-15 17:42:01 UTC

NP-MRD ID

NP0023538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apramycin

Provided By

NPAtlas

Description

Apramycin is also known as apramicina or nebramycin II. Apramycin is a drug which is used for the treatment of bacterial infections in animals. Apramycin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Apramycin is found in Streptomyces. It was first documented in 1976 (PMID: 932851). Based on a literature review a small amount of articles have been published on Apramycin (PMID: 1249675) (PMID: 340441) (PMID: 690031).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652307042108193D          

 78 81  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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    5.1702    1.8177    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    2.0287   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.7303    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -2.6454    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -3.4919   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 22 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36  3  1  0
 15  6  1  0
 35 18  1  0
 32 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  1
  4 43  1  6
  6 44  1  6
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  1
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  0
 15 54  1  6
 16 55  1  0
 18 56  1  6
 19 57  1  0
 19 58  1  0
 20 59  1  6
 21 60  1  0
 21 61  1  0
 22 62  1  6
 24 63  1  6
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  1
 29 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 32 74  1  1
 33 75  1  0
 35 76  1  1
 36 77  1  1
 37 78  1  0
M  END


  Mrv1652307042108193D          

 78 81  0  0  0  0            999 V2000
   -0.4969   -1.2070   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836   -1.9346   -1.4458 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7152   -1.5066   -0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2165   -0.1080    0.0160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6168   -0.0263    0.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.7273   -0.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0335   -0.1406   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9438   -0.7170   -0.6878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7466   -1.7403   -1.4727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9053   -2.7027   -1.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912    0.3317   -0.1450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7623    0.4292    1.3051 N   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4728    1.6791   -0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6021    1.5624   -2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    1.8817   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9459    1.9611    1.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202    0.6222    1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    0.6177    0.9529 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2810    1.6572    1.8712 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7822    1.5452    1.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259    1.7908    2.8764 N   0  0  2  0  0  0  0  0  0  0  0  0
    2.1303    0.2360    1.0052 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5167    0.1413    1.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1990   -0.2439 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8564   -1.1186   -0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3682   -1.2720   -1.7473 N   0  0  2  0  0  0  0  0  0  0  0  0
    5.9627   -1.0929    0.6091 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0179   -0.1205    0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0357   -0.8599   -0.6091 N   0  0  2  0  0  0  0  0  0  0  0  0
    6.4253    0.9927   -0.7205 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2303    2.1329   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0361    1.3703   -0.2596 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5866    2.4144   -1.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.8608    1.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -0.7266    1.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5862   -1.8719    0.8218 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3792   -2.5578    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -1.8530   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.3246   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.9502   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3317   -2.9425   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -2.1521    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    0.4843   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    1.1378   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.2401    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2923   -1.2686   -2.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5351   -2.1953   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5582   -3.3133   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9409    0.0906   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394    1.2662    1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2608   -0.3938    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0678    2.5122   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8713    2.1284   -2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7138    2.8560   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038    2.7299    1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207    0.8023   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    2.6426    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    1.3919    2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    2.3526    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    2.3497    2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483    0.9031    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.3389   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.3102   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -1.9433   -0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -1.3669   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006   -1.9870   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -2.0837    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -0.6387    1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    0.3162    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948   -1.8416   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9909   -0.4223   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840    0.8281   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    2.7687   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1702    1.8177    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    2.0287   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.7303    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -2.6454    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -3.4919   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36  3  1  0  0  0  0
 15  6  1  0  0  0  0
 35 18  1  0  0  0  0
 32 24  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  2 41  1  0  0  0  0
  3 42  1  1  0  0  0
  4 43  1  6  0  0  0
  6 44  1  6  0  0  0
  8 45  1  1  0  0  0
  9 46  1  0  0  0  0
  9 47  1  0  0  0  0
 10 48  1  0  0  0  0
 11 49  1  1  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 13 52  1  1  0  0  0
 14 53  1  0  0  0  0
 15 54  1  6  0  0  0
 16 55  1  0  0  0  0
 18 56  1  6  0  0  0
 19 57  1  0  0  0  0
 19 58  1  0  0  0  0
 20 59  1  6  0  0  0
 21 60  1  0  0  0  0
 21 61  1  0  0  0  0
 22 62  1  6  0  0  0
 24 63  1  6  0  0  0
 25 64  1  1  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
 27 67  1  0  0  0  0
 27 68  1  0  0  0  0
 28 69  1  1  0  0  0
 29 70  1  0  0  0  0
 29 71  1  0  0  0  0
 30 72  1  6  0  0  0
 31 73  1  0  0  0  0
 32 74  1  1  0  0  0
 33 75  1  0  0  0  0
 35 76  1  1  0  0  0
 36 77  1  1  0  0  0
 37 78  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@]([H])(O[C@@]2([H])O[C@@]3([H])C([H])([H])[C@@]([H])(N([H])[H])[C@@]([H])(O[C@@]4([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(N([H])[H])C([H])([H])[C@]4([H])N([H])[H])O[C@]3([H])[C@]([H])(O[H])[C@]2([H])N([H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])N([H])[H]

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
XZNUGFQTQHRASN-XQENGBIVSA-N

> <FORMULA>
C21H41N5O11

> <MOLECULAR_WEIGHT>
539.5771

> <EXACT_MASS>
539.280257179

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.459241740375845

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6S)-2-{[(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]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol

> <ALOGPS_LOGP>
-2.77

> <JCHEM_LOGP>
-6.508110424333332

> <ALOGPS_LOGS>
-1.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
5

> <JCHEM_PKA>
13.010686497531687

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.289232377008169

> <JCHEM_PKA_STRONGEST_BASIC>
9.531348696338803

> <JCHEM_POLAR_SURFACE_AREA>
283.64

> <JCHEM_REFRACTIVITY>
120.91429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apramycin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
   -0.4969   -1.2070   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836   -1.9346   -1.4458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -1.5066   -0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2165   -0.1080    0.0160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6168   -0.0263    0.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.7273   -0.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0335   -0.1406   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9438   -0.7170   -0.6878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7466   -1.7403   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9053   -2.7027   -1.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912    0.3317   -0.1450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7623    0.4292    1.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4728    1.6791   -0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6021    1.5624   -2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    1.8817   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9459    1.9611    1.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202    0.6222    1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    0.6177    0.9529 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2810    1.6572    1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822    1.5452    1.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259    1.7908    2.8764 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303    0.2360    1.0052 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5167    0.1413    1.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1990   -0.2439 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8564   -1.1186   -0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3682   -1.2720   -1.7473 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9627   -1.0929    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179   -0.1205    0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0357   -0.8599   -0.6091 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4253    0.9927   -0.7205 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2303    2.1329   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0361    1.3703   -0.2596 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5866    2.4144   -1.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.8608    1.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -0.7266    1.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5862   -1.8719    0.8218 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3792   -2.5578    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -1.8530   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.3246   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.9502   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3317   -2.9425   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -2.1521    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    0.4843   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    1.1378   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.2401    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2923   -1.2686   -2.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5351   -2.1953   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5582   -3.3133   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9409    0.0906   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394    1.2662    1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2608   -0.3938    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0678    2.5122   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8713    2.1284   -2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7138    2.8560   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038    2.7299    1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207    0.8023   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    2.6426    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    1.3919    2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    2.3526    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    2.3497    2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483    0.9031    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.3389   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.3102   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -1.9433   -0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -1.3669   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006   -1.9870   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -2.0837    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -0.6387    1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    0.3162    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948   -1.8416   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9909   -0.4223   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840    0.8281   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    2.7687   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1702    1.8177    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    2.0287   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.7303    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -2.6454    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -3.4919   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 22 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36  3  1  0
 15  6  1  0
 35 18  1  0
 32 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  1
  4 43  1  6
  6 44  1  6
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  1
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  0
 15 54  1  6
 16 55  1  0
 18 56  1  6
 19 57  1  0
 19 58  1  0
 20 59  1  6
 21 60  1  0
 21 61  1  0
 22 62  1  6
 24 63  1  6
 25 64  1  1
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  1
 29 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 32 74  1  1
 33 75  1  0
 35 76  1  1
 36 77  1  1
 37 78  1  0
M  END

HEADER    PROTEIN                                 04-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-21         0                                  
HETATM    1  C   UNK     0      -0.497  -1.207  -2.157  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.484  -1.935  -1.446  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.715  -1.507  -0.076  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.216  -0.108   0.016  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.617  -0.026   0.126  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.178   0.727  -0.888  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.034  -0.141  -1.601  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.944  -0.717  -0.688  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.747  -1.740  -1.473  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.905  -2.703  -1.998  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.891   0.332  -0.145  0.00  0.00           C+0
HETATM   12  N   UNK     0      -6.762   0.429   1.305  0.00  0.00           N+0
HETATM   13  C   UNK     0      -6.473   1.679  -0.713  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.602   1.562  -2.112  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.018   1.882  -0.335  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.946   1.961   1.036  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.720   0.622   1.095  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.333   0.618   0.953  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.281   1.657   1.871  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.782   1.545   1.679  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.526   1.791   2.876  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.130   0.236   1.005  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.517   0.141   1.023  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.087   0.199  -0.244  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.856  -1.119  -0.413  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.368  -1.272  -1.747  0.00  0.00           N+0
HETATM   27  C   UNK     0       5.963  -1.093   0.609  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.018  -0.121   0.087  0.00  0.00           C+0
HETATM   29  N   UNK     0       8.036  -0.860  -0.609  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.425   0.993  -0.721  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.230   2.133  -0.485  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.036   1.370  -0.260  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.587   2.414  -1.066  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.502  -0.861   1.531  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.119  -0.727   1.472  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.586  -1.872   0.822  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.379  -2.558   0.045  0.00  0.00           O+0
HETATM   38  H   UNK     0      -0.184  -1.853  -3.030  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.990  -0.325  -2.644  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.421  -0.950  -1.637  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.332  -2.942  -1.522  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.594  -2.152   0.246  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.932   0.484  -0.899  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.471   1.138  -1.605  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.417  -1.240   0.136  0.00  0.00           H+0
HETATM   46  H   UNK     0      -7.292  -1.269  -2.315  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.535  -2.195  -0.827  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.558  -3.313  -1.317  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.941   0.091  -0.401  0.00  0.00           H+0
HETATM   50  H   UNK     0      -7.339   1.266   1.584  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.261  -0.394   1.706  0.00  0.00           H+0
HETATM   52  H   UNK     0      -7.068   2.512  -0.330  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.871   2.128  -2.497  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.714   2.856  -0.801  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.404   2.730   1.361  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.121   0.802  -0.099  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.104   2.643   1.557  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.005   1.392   2.920  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.059   2.353   0.950  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.413   2.350   2.695  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.848   0.903   3.320  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.856   0.339  -0.084  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.324   0.310  -1.046  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.146  -1.943  -0.198  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.627  -1.367  -2.446  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.101  -1.987  -1.744  0.00  0.00           H+0
HETATM   67  H   UNK     0       6.388  -2.084   0.818  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.522  -0.639   1.543  0.00  0.00           H+0
HETATM   69  H   UNK     0       7.495   0.316   1.012  0.00  0.00           H+0
HETATM   70  H   UNK     0       8.095  -1.842  -0.215  0.00  0.00           H+0
HETATM   71  H   UNK     0       8.991  -0.422  -0.477  0.00  0.00           H+0
HETATM   72  H   UNK     0       6.484   0.828  -1.817  0.00  0.00           H+0
HETATM   73  H   UNK     0       7.111   2.769  -1.260  0.00  0.00           H+0
HETATM   74  H   UNK     0       5.170   1.818   0.769  0.00  0.00           H+0
HETATM   75  H   UNK     0       3.882   2.029  -1.659  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.206  -0.730   2.558  0.00  0.00           H+0
HETATM   77  H   UNK     0      -0.878  -2.645   1.595  0.00  0.00           H+0
HETATM   78  H   UNK     0       0.101  -3.492  -0.130  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3   41                                                  
CONECT    3    2    4   36   42                                             
CONECT    4    3    5   17   43                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   15   44                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   11   45                                             
CONECT    9    8   10   46   47                                             
CONECT   10    9   48                                                       
CONECT   11    8   12   13   49                                             
CONECT   12   11   50   51                                                  
CONECT   13   11   14   15   52                                             
CONECT   14   13   53                                                       
CONECT   15   13   16    6   54                                             
CONECT   16   15   55                                                       
CONECT   17    4   18                                                       
CONECT   18   17   19   35   56                                             
CONECT   19   18   20   57   58                                             
CONECT   20   19   21   22   59                                             
CONECT   21   20   60   61                                                  
CONECT   22   20   23   34   62                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   32   63                                             
CONECT   25   24   26   27   64                                             
CONECT   26   25   65   66                                                  
CONECT   27   25   28   67   68                                             
CONECT   28   27   29   30   69                                             
CONECT   29   28   70   71                                                  
CONECT   30   28   31   32   72                                             
CONECT   31   30   73                                                       
CONECT   32   30   33   24   74                                             
CONECT   33   32   75                                                       
CONECT   34   22   35                                                       
CONECT   35   34   36   18   76                                             
CONECT   36   35   37    3   77                                             
CONECT   37   36   78                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    3                                                            
CONECT   43    4                                                            
CONECT   44    6                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   21                                                            
CONECT   62   22                                                            
CONECT   63   24                                                            
CONECT   64   25                                                            
CONECT   65   26                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   27                                                            
CONECT   69   28                                                            
CONECT   70   29                                                            
CONECT   71   29                                                            
CONECT   72   30                                                            
CONECT   73   31                                                            
CONECT   74   32                                                            
CONECT   75   33                                                            
CONECT   76   35                                                            
CONECT   77   36                                                            
CONECT   78   37                                                            
MASTER        0    0    0    0    0    0    0    0   78    0  162    0
END

RDKit          3D

78 81  0  0  0  0  0  0  0  0999 V2000
   -0.4969   -1.2070   -2.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836   -1.9346   -1.4458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -1.5066   -0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2165   -0.1080    0.0160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6168   -0.0263    0.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1785    0.7273   -0.8875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0335   -0.1406   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9438   -0.7170   -0.6878 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7466   -1.7403   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9053   -2.7027   -1.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8912    0.3317   -0.1450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7623    0.4292    1.3051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4728    1.6791   -0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6021    1.5624   -2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0175    1.8817   -0.3351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9459    1.9611    1.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202    0.6222    1.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    0.6177    0.9529 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2810    1.6572    1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822    1.5452    1.6793 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259    1.7908    2.8764 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303    0.2360    1.0052 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5167    0.1413    1.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871    0.1990   -0.2439 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8564   -1.1186   -0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3682   -1.2720   -1.7473 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9627   -1.0929    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179   -0.1205    0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0357   -0.8599   -0.6091 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4253    0.9927   -0.7205 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2303    2.1329   -0.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0361    1.3703   -0.2596 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5866    2.4144   -1.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.8608    1.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -0.7266    1.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5862   -1.8719    0.8218 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3792   -2.5578    0.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -1.8530   -3.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.3246   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212   -0.9502   -1.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3317   -2.9425   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -2.1521    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    0.4843   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    1.1378   -1.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4169   -1.2401    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2923   -1.2686   -2.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5351   -2.1953   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5582   -3.3133   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9409    0.0906   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3394    1.2662    1.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2608   -0.3938    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0678    2.5122   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8713    2.1284   -2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7138    2.8560   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4038    2.7299    1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207    0.8023   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    2.6426    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    1.3919    2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    2.3526    0.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4133    2.3497    2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483    0.9031    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.3389   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.3102   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1457   -1.9433   -0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -1.3669   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1006   -1.9870   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -2.0837    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217   -0.6387    1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4947    0.3162    1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948   -1.8416   -0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9909   -0.4223   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840    0.8281   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    2.7687   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1702    1.8177    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822    2.0287   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060   -0.7303    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -2.6454    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -3.4919   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
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 27 28  1  0
 28 29  1  0
 28 30  1  0
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 30 32  1  0
 32 33  1  0
 22 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
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 15  6  1  0
 35 18  1  0
 32 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  3 42  1  1
  4 43  1  6
  6 44  1  6
  8 45  1  1
  9 46  1  0
  9 47  1  0
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 32 74  1  1
 33 75  1  0
 35 76  1  1
 36 77  1  1
 37 78  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
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	ChEBI
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	ChEBI
Apramicina	ChEBI
Apramycine	ChEBI
Apramycinum	ChEBI
Nebramycin factor 2	ChEBI
Nebramycin II	ChEBI
ABBR apr	Kegg
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-a-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine	Generator
4-O-((8R)-2-Amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine	Generator
4-O-(3a-Amino-6a-((4-amino-4-deoxy-a-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8b-hydroxy-7b-(methylamino)pyrano(3,2-b)pyran-2a-yl)-2-deoxy-D-streptamine	Generator
4-O-(3Α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamine	Generator
Apramycin sulfate	MeSH

Chemical Formula

C₂₁H₄₁N₅O₁₁

Average Mass

539.5771 Da

Monoisotopic Mass

539.28026 Da

IUPAC Name

(2R,3R,4S,5S,6S)-2-{[(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]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol

Traditional Name

apramycin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

XZNUGFQTQHRASN-XQENGBIVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	NPAtlas	932851

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Amino cyclitol glycoside
Hexose monosaccharide
Aminocyclitol or derivatives
Cyclohexylamine
Cyclohexanol
Oxane
Cyclitol or derivatives
Monosaccharide
1,3-aminoalcohol
Cyclic alcohol
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Secondary amine
Acetal
Secondary aliphatic amine
Organopnictogen compound
Primary aliphatic amine
Organonitrogen compound
Primary alcohol
Organic nitrogen compound
Amine
Alcohol
Primary amine
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:2790 )
aminoglycoside (CHEBI:2790 )
2-deoxystreptamine derivative (CHEBI:2790 )

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	-2.8	ALOGPS
logP	-6.5	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	5	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	283.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.91 m³·mol⁻¹	ChemAxon
Polarizability	54.46 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

NPAtlas ID

NPA024656

HMDB ID

Not Available

DrugBank ID

DB04626

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2339128

KEGG Compound ID

C01555

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Apramycin

METLIN ID

Not Available

PubChem Compound

3081545

PDB ID

Not Available

ChEBI ID

2790

Good Scents ID

Not Available

References

General References

O'Connor S, Lam LK, Jones ND, Chaney MO: Apramycin, a unique aminocyclitol antibiotic. J Org Chem. 1976 Jun 11;41(12):2087-92. doi: 10.1021/jo00874a003. [PubMed:932851 ]
Wenkert E, Hagaman EW: Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XXXIX. Apramycin--an application of amine protonation parameters. J Org Chem. 1976 Feb 20;41(4):701-2. doi: 10.1021/jo00866a025. [PubMed:1249675 ]
Ryden R, Moore BJ: The in vitro activity of apramycin, a new aminocyclitol antibiotic. J Antimicrob Chemother. 1977 Nov;3(6):609=13. doi: 10.1093/jac/3.6.609. [PubMed:340441 ]
Walton JR: Apramycin, a new aminocyclitol antibiotic. I. In vitro microbiological studies. J Antimicrob Chemother. 1978 Jul;4(4):309-13. doi: 10.1093/jac/4.4.309. [PubMed:690031 ]

Showing NP-Card for Apramycin (NP0023538)

MOL for NP0023538 (Apramycin)

3D MOL for NP0023538 (Apramycin)

3D SDF for NP0023538 (Apramycin)

3D-SDF for NP0023538 (Apramycin)

PDB for NP0023538 (Apramycin)

3D PDB for NP0023538 (Apramycin)

SMILES for NP0023538 (Apramycin)

INCHI for NP0023538 (Apramycin)

Structure for NP0023538 (Apramycin)

3D Structure for NP0023538 (Apramycin)