NP-MRD: Showing NP-Card for 2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0154639)

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Record Information

Version

2.0

Created at

2022-09-02 11:35:11 UTC

Updated at

2022-09-02 11:35:11 UTC

NP-MRD ID

NP0154639

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Validamycin C belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Streptomyces hygroscopicus. Validamycin C is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512262D          

 45 48  0  0  0  0            999 V2000
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 23  1  0  0  0  0
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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 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
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

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   -8.3199    0.2178    2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8775    0.1849    0.6471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0287    1.2569    0.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1510    0.6483   -0.6601 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3255   -0.1519    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9815    0.1021   -0.0185 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4887    0.9581    1.1697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0823    0.3777    2.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375    0.9192    1.3323 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.1926    0.2841    0.2220 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.5969   -1.6369   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7591    1.4151   -2.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3342    1.3659    0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.0133    1.3813   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3251   -0.9477   -2.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2199   -1.8830   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2353   -1.4228    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
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 39 38  1  0
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 40 85  1  1
 41 86  1  0
M  END


  Mrv1533004251512262D          

 45 48  0  0  0  0            999 V2000
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   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 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
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 35 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1CC(NC2C=C(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H45NO18/c28-3-7-1-9(15(33)21(39)24(7)45-26-23(41)20(38)17(35)12(5-30)44-26)27-10-2-8(13(31)18(36)14(10)32)6-42-25-22(40)19(37)16(34)11(4-29)43-25/h2,7,9-41H,1,3-6H2

> <INCHI_KEY>
IUZLKGXGTJOZDV-UHFFFAOYSA-N

> <FORMULA>
C26H45NO18

> <MOLECULAR_WEIGHT>
659.635

> <EXACT_MASS>
659.263663613

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
63.306895645401546

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.99

> <JCHEM_LOGP>
-8.703096026666667

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.377484987875349

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884293111538096

> <JCHEM_PKA_STRONGEST_BASIC>
7.710670231620642

> <JCHEM_POLAR_SURFACE_AREA>
332.17

> <JCHEM_REFRACTIVITY>
142.88420000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21                                                            
CONECT   23    9   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    7   28                                                  
CONECT   28   27                                                            
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   44                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   35   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
Validamycin g	MeSH
Validamycin e	MeSH
Validamycins	MeSH
Validamycin F	MeSH
Validamycin D	MeSH

Chemical Formula

C₂₆H₄₅NO₁₈

Average Mass

659.6350 Da

Monoisotopic Mass

659.26366 Da

IUPAC Name

2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1CC(NC2C=C(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H45NO18/c28-3-7-1-9(15(33)21(39)24(7)45-26-23(41)20(38)17(35)12(5-30)44-26)27-10-2-8(13(31)18(36)14(10)32)6-42-25-22(40)19(37)16(34)11(4-29)43-25/h2,7,9-41H,1,3-6H2

InChI Key

IUZLKGXGTJOZDV-UHFFFAOYSA-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 hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Polyol
Secondary amine
Oxacycle
Acetal
Secondary aliphatic amine
Primary alcohol
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organonitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-3	ALOGPS
logP	-8.7	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	7.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	332.17 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	142.88 m³·mol⁻¹	ChemAxon
Polarizability	63.31 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

166727

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0154639)

MOL for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0154639 (2-[(3-{[2,3-dihydroxy-5-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]amino}-4,5,6-trihydroxycyclohex-1-en-1-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)