NP-MRD: Showing NP-Card for Maduramycin C (NP0333613)

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Record Information

Version

2.0

Created at

2024-07-16 06:56:42 UTC

Updated at

2024-11-01 00:18:34 UTC

NP-MRD ID

NP0333613

Natural Product DOI

https://doi.org/10.57994/3092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Maduramycin C

Description

Maduramycin C belongs to the class of organic compounds known as fatty acyl glycosides. Fatty acyl glycosides are compounds containing fatty acyl chain linked to a carbohydrate moiety through a glycosidic bond. Fatty acyl glycosides are composed of a glycosyl moiety (one or several units) linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Based on a literature review very few articles have been published on Maduramycin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03302309302D          

 60 64  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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  1  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  2  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  1  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
   -0.7145   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -14.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  2  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
    2.1434   -5.3625    0.0000 O   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
    1.4289   -1.6500    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
    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 C   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 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12  9  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 18  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 35 32  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 30  1  0  0  0  0
 39 40  1  6  0  0  0
 41 27  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 25  1  0  0  0  0
 45 46  1  6  0  0  0
 23 47  1  0  0  0  0
 47 16  1  0  0  0  0
 47 48  1  6  0  0  0
 14 49  1  0  0  0  0
 49  7  1  0  0  0  0
 49 50  1  6  0  0  0
  5 51  2  0  0  0  0
  2 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
M  END


  Mrv2104 03302309302D          

 60 64  0  0  1  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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  1  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  2  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  1  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
   -0.7145   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000  -14.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  2  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
    2.1434   -5.3625    0.0000 O   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
    1.4289   -1.6500    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
    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 C   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 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12  9  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 18  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 35 32  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 30  1  0  0  0  0
 39 40  1  6  0  0  0
 41 27  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 25  1  0  0  0  0
 45 46  1  6  0  0  0
 23 47  1  0  0  0  0
 47 16  1  0  0  0  0
 47 48  1  6  0  0  0
 14 49  1  0  0  0  0
 49  7  1  0  0  0  0
 49 50  1  6  0  0  0
  5 51  2  0  0  0  0
  2 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C(=O)N[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O[C@H]3O[C@@H](CO[C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1O)=C/C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C38H55NO21/c1-16(6-5-9-17-7-3-2-4-8-17)10-11-22(43)39-35-31(52)33(25(46)19(13-41)55-35)59-38-32(53)34(26(47)20(14-42)57-38)60-37-30(51)28(49)24(45)21(58-37)15-54-36-29(50)27(48)23(44)18(12-40)56-36/h2-11,18-21,23-38,40-42,44-53H,12-15H2,1H3,(H,39,43)/b9-5+,11-10+,16-6+/t18-,19-,20-,21-,23-,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+/m0/s1

> <INCHI_KEY>
AWGWUQCFFPNKDC-PDOVIGOJSA-N

> <FORMULA>
C38H55NO21

> <MOLECULAR_WEIGHT>
861.844

> <EXACT_MASS>
861.326657795

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
87.14134433278656

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-methyl-7-phenylhepta-2,4,6-trienamide

> <JCHEM_LOGP>
-4.875856755999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.904306926496842

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.431517467625143

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6552454516958686

> <JCHEM_POLAR_SURFACE_AREA>
356.7

> <JCHEM_REFRACTIVITY>
199.60000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-methyl-7-phenylhepta-2,4,6-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-23         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334 -10.010   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334 -20.790   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334 -20.790   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334 -25.410   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.000 -26.180   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334 -25.410   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335 -26.180   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667 -27.720   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001 -28.490   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334 -28.490   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334 -30.030   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.000 -27.720   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.334 -28.490   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -4.001 -25.410   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   49                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   49                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   47                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   47                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   45                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   41                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   39                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   30   40                                                  
CONECT   40   39                                                            
CONECT   41   27   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   25   46                                                  
CONECT   46   45                                                            
CONECT   47   23   16   48                                                  
CONECT   48   47                                                            
CONECT   49   14    7   50                                                  
CONECT   50   49                                                            
CONECT   51    5                                                            
CONECT   52    2   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   55                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₅₅NO₂₁

Average Mass

861.8440 Da

Monoisotopic Mass

861.32666 Da

IUPAC Name

(2E,4E,6E)-N-[(2S,3S,4R,5S,6S)-4-{[(2R,3S,4R,5S,6S)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-({[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-methyl-7-phenylhepta-2,4,6-trienamide

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C(=O)N[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O[C@H]3O[C@@H](CO[C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)[C@H](O)[C@@H](O)[C@@H]3O)[C@@H]2O)[C@@H]1O)=C/C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C38H55NO21/c1-16(6-5-9-17-7-3-2-4-8-17)10-11-22(43)39-35-31(52)33(25(46)19(13-41)55-35)59-38-32(53)34(26(47)20(14-42)57-38)60-37-30(51)28(49)24(45)21(58-37)15-54-36-29(50)27(48)23(44)18(12-40)56-36/h2-11,18-21,23-38,40-42,44-53H,12-15H2,1H3,(H,39,43)/b9-5+,11-10+,16-6+/t18-,19-,20-,21-,23-,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+/m0/s1

InChI Key

AWGWUQCFFPNKDC-PDOVIGOJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, C2D6OS, experimental)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.152470926, C2D6OS, simulated)	dg20300089@smail.nju.edu.cn	Nanjing University	Yan Zou	2024-07-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
glauciflava		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty acyl glycosides. These are compounds containing fatty acyl chain linked to a carbohydrate moiety through a glycosidic bond. Fatty acyl glycosides are composed of a glycosyl moiety (one or several units) linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides

Alternative Parents

Substituents

Fatty n-acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Amino saccharide
Benzenoid
Oxane
N-acyl-amine
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxamide group
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-4.9	ChemAxon
pKa (Strongest Acidic)	11.43	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	356.7 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	199.6 m³·mol⁻¹	ChemAxon
Polarizability	87.14 Å³	ChemAxon
Number of Rings	5	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Maduramycin C (NP0333613)

MOL for NP0333613 (Maduramycin C)

3D MOL for NP0333613 (Maduramycin C)

3D SDF for NP0333613 (Maduramycin C)

3D-SDF for NP0333613 (Maduramycin C)

PDB for NP0333613 (Maduramycin C)

3D PDB for NP0333613 (Maduramycin C)

SMILES for NP0333613 (Maduramycin C)

INCHI for NP0333613 (Maduramycin C)

Structure for NP0333613 (Maduramycin C)

3D Structure for NP0333613 (Maduramycin C)