NP-MRD: Showing NP-Card for (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0197077)

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Record Information

Version

2.0

Created at

2022-09-04 15:16:33 UTC

Updated at

2022-09-04 15:16:33 UTC

NP-MRD ID

NP0197077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid

Description

8-Methoxychlortetracycline 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. (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid was first documented in 1987 (PMID: 3680007). Based on a literature review a small amount of articles have been published on 8-methoxychlortetracycline (PMID: 3680006) (PMID: 3680005).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217162D          

 35 38  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7565   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   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
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
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 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

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   -0.6919    1.6246   -0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8792    2.8332   -0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6103    0.9884   -0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    1.7311   -0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4707    3.0877    0.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821    1.1530    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816    1.8665    0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133    3.1906    0.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3207    1.2058    0.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394   -0.1245    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791   -0.7722    0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8266   -0.0644    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3128   -0.8177   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5309   -2.5413   -0.3370 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.2064   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738   -1.0777   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3844   -1.7672   -1.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -2.1091    0.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467   -0.4523   -0.6990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4252   -1.0763    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -0.6233   -0.3316 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2966   -3.0905    0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0901   -1.6470    0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040    0.4435    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    0.7283    2.4483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828    3.9066   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505    1.9558   -2.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9310   -0.3044   -2.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774    3.4237    1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226    3.8473    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1615    1.8179    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8317   -0.0527    2.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7133   -0.6883    0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9078    0.9398    0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6118   -1.5858   -2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3222   -1.3624   -2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267   -2.8719   -1.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874   -2.9477   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -0.5587   -1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -0.6724    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -2.1826    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195   -1.3689   -1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -1.2382    1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9888   -3.1969   -0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
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 21 20  1  0
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 35 36  2  0
 35  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
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 10 11  2  0
 28 25  1  0
 25 26  1  0
 25 27  1  1
 25 24  1  0
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 22 19  1  0
 24 15  1  0
 10 12  1  0
  8 30  1  0
 21 43  1  0
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 18 42  1  0
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  4 37  1  0
  2  1  1  0
  7 38  1  0
  9 39  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
M  END


  Mrv1652309042217162D          

 35 38  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7565   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   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
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
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 23 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(O)=C3[C@H](C[C@H]4[C@H](N(C)C)C(=O)C(C(O)=N)=C(O)[C@@]4(O)C3=O)[C@](C)(O)C2=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C23H25ClN2O9/c1-22(33)7-5-8-16(26(2)3)18(29)13(21(25)32)20(31)23(8,34)19(30)11(7)17(28)12-9(27)6-10(35-4)15(24)14(12)22/h6-8,16,27-28,31,33-34H,5H2,1-4H3,(H2,25,32)/t7-,8-,16-,22-,23-/m0/s1

> <INCHI_KEY>
LITNLJPOCNTUJW-QYPDEEGYSA-N

> <FORMULA>
C23H25ClN2O9

> <MOLECULAR_WEIGHT>
508.91

> <EXACT_MASS>
508.1248581

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.87202410232153

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

> <JCHEM_LOGP>
-5.214625491874204

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
0.7468255531466004

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.963846134154001

> <JCHEM_PKA_STRONGEST_BASIC>
13.571244136675517

> <JCHEM_POLAR_SURFACE_AREA>
191.83999999999997

> <JCHEM_REFRACTIVITY>
136.22449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       5.335  -3.080   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.012  -3.440   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.992  -3.440   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      17.338  -6.930   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   34                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   16   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   14   34                                                  
CONECT   34   33    7   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₅ClN₂O₉

Average Mass

508.9100 Da

Monoisotopic Mass

508.12486 Da

IUPAC Name

(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

Traditional Name

(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(O)=C3[C@H](C[C@H]4[C@H](N(C)C)C(=O)C(C(O)=N)=C(O)[C@@]4(O)C3=O)[C@](C)(O)C2=C1Cl

InChI Identifier

InChI=1S/C23H25ClN2O9/c1-22(33)7-5-8-16(26(2)3)18(29)13(21(25)32)20(31)23(8,34)19(30)11(7)17(28)12-9(27)6-10(35-4)15(24)14(12)22/h6-8,16,27-28,31,33-34H,5H2,1-4H3,(H2,25,32)/t7-,8-,16-,22-,23-/m0/s1

InChI Key

LITNLJPOCNTUJW-QYPDEEGYSA-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
Anthracene carboxylic acid or derivatives
1-naphthol
Naphthalene
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Aryl chloride
Aryl halide
Benzenoid
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Tertiary amine
Primary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Tertiary aliphatic amine
Cyclic ketone
Ketone
Polyol
Ether
Carboxylic acid derivative
Enol
Alcohol
Organohalogen compound
Organochloride
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
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	-5.2	ChemAxon
pKa (Strongest Acidic)	-4	ChemAxon
pKa (Strongest Basic)	13.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	191.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.22 m³·mol⁻¹	ChemAxon
Polarizability	48.87 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	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

58190420

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54692978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Smith EB, Munayyer HK, Ryan MJ, Mayles BA, Hegde VR, Miller GH: Direct selection of a specifically blocked mutant of Actinomadura brunnea. Isolation of a third 8-methoxy substituted chlortetracycline. J Antibiot (Tokyo). 1987 Oct;40(10):1419-25. doi: 10.7164/antibiotics.40.1419. [PubMed:3680007 ]
Patel M, Gullo VP, Hegde VR, Horan AC, Marquez JA, Vaughan R, Puar MS, Miller GH: A new tetracycline antibiotic from a Dactylosporangium species. Fermentation, isolation and structure elucidation. J Antibiot (Tokyo). 1987 Oct;40(10):1414-8. doi: 10.7164/antibiotics.40.1414. [PubMed:3680006 ]
Patel M, Gullo VP, Hegde VR, Horan AC, Gentile F, Marquez JA, Miller GH, Puar MS, Waitz JA: A novel tetracycline from Actinomadura brunnea. Fermentation, isolation and structure elucidation. J Antibiot (Tokyo). 1987 Oct;40(10):1408-13. doi: 10.7164/antibiotics.40.1408. [PubMed:3680005 ]
LOTUS database [Link]

Showing NP-Card for (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0197077)

MOL for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D MOL for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D SDF for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D-SDF for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

PDB for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D PDB for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

SMILES for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

INCHI for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

Structure for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D Structure for NP0197077 ((4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-8-methoxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)