NP-MRD: Showing NP-Card for 4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0241756)

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Record Information

Version

2.0

Created at

2022-09-07 01:54:48 UTC

Updated at

2022-09-07 01:54:48 UTC

NP-MRD ID

NP0241756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid

Description

4-(Dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups. 4-(Dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261515112D          

 32 35  0  0  0  0            999 V2000
    1.6131   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 10 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  2 32  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -2.4546   -3.1932    0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -1.9602    0.3183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1039   -1.4592    1.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.9630   -0.1631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8271    0.1859   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939    0.2195   -2.0193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289    1.2875    0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849    1.9925   -0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3405    1.6398   -1.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339    2.9474    0.5562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258    1.6121    1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    2.6694    1.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594    0.8892    1.2944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9003    1.0266    2.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    1.6580    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    2.9037    0.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    1.0116    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232    1.6646    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    3.0012    0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448    1.0673   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6260    1.8105   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6274    3.1326   -0.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7678    1.2483   -1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7054   -0.0607   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -0.7949   -1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3689   -0.2350   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1599   -1.0848   -0.7793 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5441   -2.2042    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674   -1.7408   -2.0176 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405   -0.3686   -0.3623 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1828   -1.1489    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858   -0.5657    0.9540 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2118   -3.9426    1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -3.0442    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -3.5829   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -0.8346    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8924   -0.9648    0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6042   -2.3409    1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -1.3651   -1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8812    0.7632   -1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4220    2.2667   -2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297    3.4949    2.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843    1.9817    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    3.1523    1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4589    3.6893   -0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729    1.8351   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491   -0.5582   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -1.8237   -1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6455   -1.8233    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8615   -3.0729    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481   -2.5519   -0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5894   -2.6419   -1.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2586   -0.3394   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0362   -2.1687    0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -1.2293    1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5493   -1.0871    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4 32  1  0
 32 31  1  0
 31 30  1  0
 30 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 26  2  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  6
 17 15  1  0
 15 16  2  0
 15 13  1  0
 13 14  1  1
 13 11  1  0
 11 12  1  0
 11  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
 13 32  1  0
 27 30  1  0
 21 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  6
 32 56  1  1
 31 54  1  0
 31 55  1  0
 30 53  1  6
 19 44  1  0
 25 48  1  0
 24 47  1  0
 23 46  1  0
 22 45  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 14 43  1  0
 12 42  1  0
  9 40  1  0
  9 41  1  0
M  END


  Mrv1533004261515112D          

 32 35  0  0  0  0            999 V2000
    1.6131   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    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  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 10 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)C1C2CC3C(=C(O)C4=C(C=CC=C4O)C3(C)O)C(=O)C2(O)C(O)=C(C(N)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)

> <INCHI_KEY>
NWXMGUDVXFXRIG-UHFFFAOYSA-N

> <FORMULA>
C22H24N2O8

> <MOLECULAR_WEIGHT>
444.44

> <EXACT_MASS>
444.153265741

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.925614788251394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-3.823037572541849

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.619650284705392

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5924308218731196

> <JCHEM_PKA_STRONGEST_BASIC>
6.5420115199014575

> <JCHEM_POLAR_SURFACE_AREA>
181.62000000000003

> <JCHEM_REFRACTIVITY>
114.01989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       3.011  -1.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      13.337   1.540   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       9.336  -2.310   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.991  -1.950   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   32                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10    5   12   24                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3   15                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   15                                                            
CONECT   24   11                                                            
CONECT   25   10                                                            
CONECT   26    9   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    6   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    2                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
4-(Dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidate	Generator

Chemical Formula

C₂₂H₂₄N₂O₈

Average Mass

444.4400 Da

Monoisotopic Mass

444.15327 Da

IUPAC Name

4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide

Traditional Name

4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

CAS Registry Number

Not Available

SMILES

CN(C)C1C2CC3C(=C(O)C4=C(C=CC=C4O)C3(C)O)C(=O)C2(O)C(O)=C(C(N)=O)C1=O

InChI Identifier

InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)

InChI Key

NWXMGUDVXFXRIG-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
1-naphthol
Naphthalene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Benzenoid
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Ketone
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Carboximidic acid
Carboximidic acid derivative
Enol
Polyol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	-0.73	ALOGPS
logP	-3.8	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.59	ChemAxon
pKa (Strongest Basic)	6.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.02 m³·mol⁻¹	ChemAxon
Polarizability	43.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

54685734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0241756)

MOL for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D MOL for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D SDF for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D-SDF for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

PDB for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D PDB for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

SMILES for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

INCHI for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

Structure for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D Structure for NP0241756 (4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)