NP-MRD: Showing NP-Card for 6-Deoxyoxytetracycline (NP0061628)

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Record Information

Version

2.0

Created at

2022-04-28 06:23:03 UTC

Updated at

2022-04-28 06:23:03 UTC

NP-MRD ID

NP0061628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Deoxyoxytetracycline

Description

Doxycycline, also known as doxiciclina or jenacyclin, 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. Thus, doxycycline is considered to be a linear tetracycline lipid molecule. Doxycycline is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, doxycycline is involved in doxycycline action pathway. 6-Deoxyoxytetracycline is found in Streptomyces hygroscopicus. 6-Deoxyoxytetracycline was first documented in 2003 (PMID: 12684759). Doxycycline is a potentially toxic compound (PMID: 15964448) (PMID: 16940111).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231214332D          
 
 34 37  0  0  1  0            999 V2000
   17.9362   -9.4212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9533  -10.2420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6558   -9.0195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2306   -9.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2132  -10.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6314  -10.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3578   -9.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5111   -9.4073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5467  -10.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2098  -11.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3508  -10.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6024  -11.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0845   -9.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7986   -8.9915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7916  -10.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0599  -10.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0859   -9.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0825  -10.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7916  -11.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7830  -10.2839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0771  -11.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3629   -8.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3665  -10.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6503   -9.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6503  -10.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3665  -11.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8018   -7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6694   -7.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3998   -7.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9526   -7.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9292   -8.5820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5069   -8.5693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2245   -7.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9208  -11.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 23 26  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
 17 18  2  0  0  0  0
 24 25  1  0  0  0  0
 14 27  1  6  0  0  0
  3 28  1  6  0  0  0
  1  2  1  0  0  0  0
 28 29  1  0  0  0  0
  1  3  1  0  0  0  0
 28 30  1  0  0  0  0
  1  4  1  0  0  0  0
  1 31  1  6  0  0  0
  2  5  1  0  0  0  0
  8 32  1  6  0  0  0
  2  6  1  0  0  0  0
  4 33  1  6  0  0  0
  3  7  1  0  0  0  0
  2 34  1  6  0  0  0
  4  8  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    2.5072    1.9024    1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498    1.3294    0.5874 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6557    0.9107    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143    1.7798    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    1.5208   -0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2199    0.3758   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.5018   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -1.6602   -1.8877 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253   -0.2166   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420   -1.1722   -0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0865   -2.1943   -1.5297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581   -0.8865   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490   -1.7278   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7602   -2.8166   -1.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -1.5480    0.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6561   -2.3499    1.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809   -2.2296   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5066   -2.9023   -1.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1623   -2.0264   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773   -3.0368   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4910   -2.9530    0.1316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488   -4.2098   -0.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -0.7568    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8471   -0.5912    0.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    0.2665   -0.0426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8657    1.5729    0.2990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5885    2.5788   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3114    1.7349    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1574   -0.1691    0.5448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0554    0.8248    0.1656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2242    2.0218    0.8530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967    0.2668    0.6323 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5488    1.8673    2.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081    1.2622    2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8275    2.9648    1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.1538   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5710    2.6805    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8424    2.1953    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2070    0.1563   -1.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2019   -1.9908   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126   -2.5742   -2.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -3.2851    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1753   -2.3716   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8391   -3.4847    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0569   -0.8894    1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2128    0.3596   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8634    2.2255   -1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5011    2.8517   -1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2809    3.5346   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6644    1.4259    1.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346    2.8728    0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926    1.4133   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.1001    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640    0.9415   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    2.7939    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -0.1395    1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
 32  2  1  0
  2  1  1  0
  2  3  1  0
  3  9  2  0
  9  7  1  0
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  7  6  2  0
  6  5  1  0
  5  4  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  2  0
 17 19  1  0
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 20 22  2  0
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 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 12 32  1  0
 29 15  1  0
 30 32  1  0
  4  3  1  0
 32 56  1  1
  2 36  1  6
  1 33  1  0
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  1 35  1  0
  8 40  1  0
  6 39  1  0
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 14 41  1  0
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 21 43  1  0
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 27 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  1
 30 54  1  6
 31 55  1  0
M  END

 
  Mrv0541 02231214332D          
 
 34 37  0  0  1  0            999 V2000
   17.9362   -9.4212    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9533  -10.2420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6558   -9.0195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2306   -9.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2132  -10.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6314  -10.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3578   -9.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5111   -9.4073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5467  -10.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2098  -11.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3508  -10.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6024  -11.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0845   -9.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7986   -8.9915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7916  -10.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0599  -10.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0859   -9.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0825  -10.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7916  -11.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7830  -10.2839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0771  -11.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3629   -8.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3665  -10.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6503   -9.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6503  -10.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3665  -11.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8018   -7.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6694   -7.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3998   -7.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9526   -7.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9292   -8.5820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5069   -8.5693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2245   -7.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9208  -11.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 15  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
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 23 25  2  0  0  0  0
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  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
 17 18  2  0  0  0  0
 24 25  1  0  0  0  0
 14 27  1  6  0  0  0
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  1  2  1  0  0  0  0
 28 29  1  0  0  0  0
  1  3  1  0  0  0  0
 28 30  1  0  0  0  0
  1  4  1  0  0  0  0
  1 31  1  6  0  0  0
  2  5  1  0  0  0  0
  8 32  1  6  0  0  0
  2  6  1  0  0  0  0
  4 33  1  6  0  0  0
  3  7  1  0  0  0  0
  2 34  1  6  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C)C3=C(C(O)=CC=C3)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

> <INCHI_KEY>
JBIWCJUYHHGXTC-AKNGSSGZSA-N

> <FORMULA>
C22H24N2O8

> <MOLECULAR_WEIGHT>
444.4346

> <EXACT_MASS>
444.153265754

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
42.88236658408105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-3.4356368980531804

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.674903996767855

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.2352759547193397

> <JCHEM_PKA_STRONGEST_BASIC>
7.751996038861081

> <JCHEM_POLAR_SURFACE_AREA>
181.61999999999998

> <JCHEM_REFRACTIVITY>
113.89189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vibramycin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      33.481 -17.586   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.513 -19.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.824 -16.836   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.164 -16.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.131 -19.875   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.779 -19.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.135 -17.625   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.821 -17.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.887 -19.099   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      32.125 -21.420   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      36.121 -19.158   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      34.724 -21.453   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      37.491 -16.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      29.491 -16.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.478 -19.868   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.445 -19.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.160 -17.547   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.154 -19.092   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      29.478 -21.407   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      38.795 -19.197   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      37.477 -21.498   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      26.811 -16.778   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.817 -19.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.481 -17.554   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.481 -19.099   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      26.817 -21.407   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      29.497 -14.838   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      34.850 -14.350   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      36.213 -13.592   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.512 -13.548   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      33.468 -16.020   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      30.813 -15.996   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0      32.152 -14.854   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      33.452 -20.676   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   31                                             
CONECT    2    1    5    6   34                                             
CONECT    3   28    1    7                                                  
CONECT    4    1   33    8                                                  
CONECT    5    9   10    2                                                  
CONECT    6   11   12    2                                                  
CONECT    7   13   11    3                                                  
CONECT    8   14    9   32    4                                             
CONECT    9    5   15    8                                                  
CONECT   10    5                                                            
CONECT   11    6   16    7                                                  
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    8   17   27                                                  
CONECT   15    9   18   19                                                  
CONECT   16   11   20   21                                                  
CONECT   17   14   22   18                                                  
CONECT   18   15   23   17                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   17   24                                                       
CONECT   23   18   25   26                                                  
CONECT   24   22   25                                                       
CONECT   25   23   24                                                       
CONECT   26   23                                                            
CONECT   27   14                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    1                                                            
CONECT   32    8                                                            
CONECT   33    4                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(4S,4AR,5S,5ar,6R,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide	ChEBI
5-Hydroxy-alpha-6-deoxytetracycline	ChEBI
6alpha-Deoxy-5-oxytetracycline	ChEBI
Doxiciclina	ChEBI
Doxycyclin	ChEBI
Doxycycline (anhydrous)	ChEBI
Doxycyclinum	ChEBI
Jenacyclin	ChEBI
Supracyclin	ChEBI
Vibramycin	ChEBI
DOXY	Kegg
Doxychel	Kegg
5-Hydroxy-a-6-deoxytetracycline	Generator
5-Hydroxy-α-6-deoxytetracycline	Generator
6a-Deoxy-5-oxytetracycline	Generator
6Α-deoxy-5-oxytetracycline	Generator
Doxcycline anhydrous	HMDB
Doxycycline hyclate	HMDB
Doxycycline monohydrate	HMDB
Doxytetracycline	HMDB

Chemical Formula

C₂₂H₂₄N₂O₈

Average Mass

444.4346 Da

Monoisotopic Mass

444.15327 Da

IUPAC Name

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

Traditional Name

vibramycin

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C)C3=C(C(O)=CC=C3)C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O

InChI Identifier

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1

InChI Key

JBIWCJUYHHGXTC-AKNGSSGZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces hygroscopicus	LOTUS Database	35616633

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
Naphthacene
Tetracene
Anthracene carboxylic acid or derivatives
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Benzenoid
Tertiary alcohol
Vinylogous acid
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Ketone
Polyol
Carboxylic acid derivative
Enol
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tetracyclines (CHEBI:50845 )
Linear tetracyclines (C06973 )
Linear tetracyclines (LMPK07000001 )

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	-0.72	ALOGPS
logP	-3.4	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	7.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	113.89 m³·mol⁻¹	ChemAxon
Polarizability	42.88 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

HMDB0014399

DrugBank ID

DB00254

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017127

Chemspider ID

10469369

KEGG Compound ID

C06973

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Doxycycline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

DXT

ChEBI ID

50845

Good Scents ID

Not Available

References

General References

Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. doi: 10.1007/s00430-002-0174-6. Epub 2003 Mar 5. [PubMed:12684759 ]
Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. doi: 10.1016/S0140-6736(05)66591-9. [PubMed:15964448 ]
Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. doi: 10.1128/AAC.00394-06. [PubMed:16940111 ]

Showing NP-Card for 6-Deoxyoxytetracycline (NP0061628)

MOL for NP0061628 (6-Deoxyoxytetracycline)

3D MOL for NP0061628 (6-Deoxyoxytetracycline)

3D SDF for NP0061628 (6-Deoxyoxytetracycline)

3D-SDF for NP0061628 (6-Deoxyoxytetracycline)

PDB for NP0061628 (6-Deoxyoxytetracycline)

3D PDB for NP0061628 (6-Deoxyoxytetracycline)

SMILES for NP0061628 (6-Deoxyoxytetracycline)

INCHI for NP0061628 (6-Deoxyoxytetracycline)

Structure for NP0061628 (6-Deoxyoxytetracycline)

3D Structure for NP0061628 (6-Deoxyoxytetracycline)