NP-MRD: Showing NP-Card for (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0321897)

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Record Information

Version

2.0

Created at

2022-09-12 00:20:59 UTC

Updated at

2022-09-12 00:20:59 UTC

NP-MRD ID

NP0321897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Oxytetracycline, also known as geomycin or terramycin, 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,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid is found in Streptomyces albidoflavus, Streptomyces lividans, Streptomyces rimosus, Streptomyces varsoviensis and Streptomyces venezuelae. (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid was first documented in 2022 (PMID: 36123536). Based on a literature review a significant number of articles have been published on oxytetracycline (PMID: 36118603) (PMID: 36108497) (PMID: 36104903) (PMID: 36103709) (PMID: 36100774) (PMID: 36097302).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202212D          

 33 36  0  0  1  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  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 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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  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
    4.2868   -2.4750    0.0000 C   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   -2.8875    0.0000 C   0  0  0  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
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   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
    7.8592   -3.7125    0.0000 C   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
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2461   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
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 15 16  2  0  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 27 30  1  0  0  0  0
 30 17  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 33 31  1  1  0  0  0
  4 33  1  0  0  0  0
 13 33  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    4.4192    0.5339   -4.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065    0.4879   -3.4192 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9094    0.5052   -2.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1015    0.4047   -1.4389 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    0.6218   -1.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608    0.7313   -2.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695    0.7359   -3.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    0.8533   -1.2917 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7173    2.1565   -1.6611 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -0.1327   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281   -0.9314   -2.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1428   -0.1150   -1.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109   -0.8787   -1.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -1.6423   -2.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3968   -0.8925   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4598   -1.6395   -1.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470   -2.4298   -2.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6999   -1.5591   -0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8417   -0.7670    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8204   -0.0245    0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678   -0.1024    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728    0.6540    0.7911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9695    2.0110    1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344   -0.0380    1.9983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450    0.7730    0.0136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0070    0.4405    0.8742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1352    1.1352    2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745    0.8284    0.2000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4396   -0.0209    0.6201 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5634   -0.2013    2.0465 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557   -0.3501    2.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -1.4210    2.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250    0.6104    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5925    1.1252    0.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1051   -0.1442   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562    0.6890   -3.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2573    2.0145   -2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -2.4933   -2.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310   -2.6393   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121   -2.1444   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8212   -0.7319    0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.6128    1.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2214    2.7949    1.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9090    2.2406    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3057    1.9529    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489   -0.9974    1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    1.8373   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -0.6250    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3235    2.0017    2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    1.8760    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -1.0196    0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -0.8737    1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9892   -1.0494    3.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756    0.5934    2.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9961   -1.2031    3.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0408    3.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705   -2.1129    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  1  0
 30 29  1  0
 29 28  1  0
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 12  1  0
 12 13  2  0
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 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 12 10  1  0
 10 11  2  0
 10  8  1  0
  8  9  1  1
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  5 33  1  0
 33 34  2  0
 33 29  1  0
  8 28  1  0
 22 25  1  0
 21 15  1  0
 31 52  1  0
 31 53  1  0
 31 54  1  0
 32 55  1  0
 32 56  1  0
 32 57  1  0
 29 51  1  6
 28 50  1  1
 26 48  1  1
 27 49  1  0
 25 47  1  6
 14 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
  9 37  1  0
  7 36  1  0
  4 35  1  0
  2  1  1  0
M  END


  Mrv1652309122202212D          

 33 36  0  0  1  0            999 V2000
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  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 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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  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
    4.2868   -2.4750    0.0000 C   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   -2.8875    0.0000 C   0  0  0  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
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   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
    7.8592   -3.7125    0.0000 C   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
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2461   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   -4.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
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 15 16  2  0  0  0  0
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 17 18  2  0  0  0  0
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 18 20  1  0  0  0  0
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 20 26  1  0  0  0  0
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 33 31  1  1  0  0  0
  4 33  1  0  0  0  0
 13 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C(O)C4=C(O)C=CC=C4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(O)=N)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

> <INCHI_KEY>
OWFJMIVZYSDULZ-PXOLEDIWSA-N

> <FORMULA>
C22H24N2O9

> <MOLECULAR_WEIGHT>
460.439

> <EXACT_MASS>
460.148180361

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.7229845022494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

> <JCHEM_LOGP>
-6.744517050205962

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
0.8221845511279033

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.6704693506519908

> <JCHEM_PKA_STRONGEST_BASIC>
13.651389528590245

> <JCHEM_POLAR_SURFACE_AREA>
202.83999999999997

> <JCHEM_REFRACTIVITY>
126.16639999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.335  -9.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.659  -8.880   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.680  -8.880   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   17   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    4   13                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Oxytetracid	MeSH
Oxytetracycline, (4a beta,5 beta,5a beta,12a beta)-isomer	MeSH
Geomycin	MeSH
Oxytetracycline anhydrous	MeSH
Oxytetracycline calcium	MeSH
Oxytetracycline, (5 beta)-isomer	MeSH
Oxytetracycline, anhydrous	MeSH
Oxytetracycline, calcium (1:1) salt	MeSH
Oxytetracycline, disodium salt, dihydrate	MeSH
Terramycin	MeSH
Bisolvomycin	MeSH
Hydroxytetracycline	MeSH
Oxyterracin	MeSH
Oxyterracine	MeSH
Oxytetracycline dihydrate	MeSH
Oxytetracycline hydrochloride	MeSH
Oxytetracycline monohydrochloride	MeSH
Oxytetracycline sulfate (2:1)	MeSH
Oxytetracycline, sodium salt	MeSH

Chemical Formula

C₂₂H₂₄N₂O₉

Average Mass

460.4390 Da

Monoisotopic Mass

460.14818 Da

IUPAC Name

(4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C(O)C4=C(O)C=CC=C4[C@@]3(C)O)C(=O)[C@]2(O)C(O)=C(C(O)=N)C1=O

InChI Identifier

InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

InChI Key

OWFJMIVZYSDULZ-PXOLEDIWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces albidoflavus	LOTUS Database	35616633
Streptomyces lividans	LOTUS Database	35616633
Streptomyces rimosus	LOTUS Database	35616633
Streptomyces varsoviensis	LOTUS Database	35616633
Streptomyces venezuelae	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
1-naphthol
Naphthalene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Benzenoid
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboximidic acid
Carboximidic acid derivative
Polyol
Enol
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Amine
Organopnictogen compound
Carbonyl group
Organic oxide
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	-6.7	ChemAxon
pKa (Strongest Acidic)	-3.7	ChemAxon
pKa (Strongest Basic)	13.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	202.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.17 m³·mol⁻¹	ChemAxon
Polarizability	43.72 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

C00017127

Chemspider ID

57267507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxytetracycline

METLIN ID

Not Available

PubChem Compound

54675779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sarkar DJ, Mohanty D, Raut SS, Kumar Das B: Antibacterial properties and in silico modeling perspective of nano ZnO transported oxytetracycline-Zn(2+) complex [ZnOTc](+) against oxytetracycline-resistant Aeromonas hydrophila. J Antibiot (Tokyo). 2022 Nov;75(11):635-649. doi: 10.1038/s41429-022-00564-0. Epub 2022 Sep 20. [PubMed:36123536 ]
Kalani M, Rahimi S, Zahraei Salehi T, Hajiaghaee R, Behnamifar A: Comparison the effects of probiotic and prebiotic as antibiotic alternatives on Salmonella colonization, performance, and egg quality in laying hens challenged with Salmonella enterica serotype Enteritidis. Iran J Vet Res. 2022;23(2):154-162. doi: 10.22099/IJVR.2022.40926.5932. [PubMed:36118603 ]
Che H, Nie Y, Tian X, Li Y: New method for morphological identification and simultaneous quantification of multiple tetracyclines by a white fluorescent probe. J Hazard Mater. 2023 Jan 5;441:129956. doi: 10.1016/j.jhazmat.2022.129956. Epub 2022 Sep 9. [PubMed:36108497 ]
Xu SJ, Chen XY, Wang XF, Sun HZ, Hou ZJ, Cheng JS, Yuan YJ: Artificial microbial consortium producing oxidases enhanced the biotransformation efficiencies of multi-antibiotics. J Hazard Mater. 2022 Oct 5;439:129674. doi: 10.1016/j.jhazmat.2022.129674. Epub 2022 Jul 25. [PubMed:36104903 ]
Girard L, Li H, Feng C, Kijak PJ, Sklenka S, Smith S, Rasmussen S, Pugh C, McDermott S, Chiesa OA, Ward J, Hasbrouck E, Smith E, Lancaster V, Qiu J: Bridging of a Liquid Chromatography-Tandem Mass Spectrometry Method for Oxytetracycline, Chlortetracycline, and Tetracycline in Bovine Kidney with the Official Microbial Growth Inhibition Assay. J AOAC Int. 2022 Dec 22;106(1):73-87. doi: 10.1093/jaoacint/qsac104. [PubMed:36103709 ]
Wang J, Yin L, Zheng W, Shi S, Hao W, Liu C, Zheng L: Lactobacillus rhamnosus GG normalizes gut dysmotility induced by environmental pollutants via affecting serotonin level in zebrafish larvae. World J Microbiol Biotechnol. 2022 Sep 14;38(12):222. doi: 10.1007/s11274-022-03409-y. [PubMed:36100774 ]
Galecio JS, Escudero E, Corrales JC, Garcia-Romero E, de la Fe C, Hernandis V, Marin P: Susceptibility of caprine mastitis pathogens to tildipirosin, gamithromycin, oxytetracycline, and danofloxacin: effect of serum on the in vitro potency of current macrolides. World J Microbiol Biotechnol. 2022 Sep 13;38(12):221. doi: 10.1007/s11274-022-03407-0. [PubMed:36097302 ]
Saric E, Quinn GA, Nalpas N, Paradzik T, Kazazic S, Filic Z, Semanjski M, Herron P, Hunter I, Macek B, Vujaklija D: Phosphoproteome Dynamics of Streptomyces rimosus during Submerged Growth and Antibiotic Production. mSystems. 2022 Oct 26;7(5):e0019922. doi: 10.1128/msystems.00199-22. Epub 2022 Sep 12. [PubMed:36094082 ]
Maqbool U, Sasanya J, Shah MS, Chughtai MI, Hussain G: Radiotracer studies to isolate in-house receptors from poultry liver for multi-chemical hazard analysis in selected food and feed. J Environ Sci Health B. 2022;57(10):804-811. doi: 10.1080/03601234.2022.2120318. Epub 2022 Sep 11. [PubMed:36093934 ]
Wang X, Wang X: UiO-66-NH(2) based fluorescent sensing for detection of tetracyclines in milk. RSC Adv. 2022 Aug 17;12(36):23427-23436. doi: 10.1039/d2ra04023a. eCollection 2022 Aug 16. [PubMed:36090428 ]
Zhang J, Xia A, Yao D, Guo X, Lam SS, Huang Y, Zhu X, Zhu X, Liao Q: Removal of oxytetracycline and ofloxacin in wastewater by microalgae-bacteria symbiosis for bioenergy production. Bioresour Technol. 2022 Nov;363:127891. doi: 10.1016/j.biortech.2022.127891. Epub 2022 Sep 8. [PubMed:36089133 ]
Matamoros V, Casas ME, Pastor E, Tadic D, Canameras N, Carazo N, Bayona JM: Effects of tetracycline, sulfonamide, fluoroquinolone, and lincosamide load in pig slurry on lettuce: Agricultural and human health implications. Environ Res. 2022 Dec;215(Pt 1):114237. doi: 10.1016/j.envres.2022.114237. Epub 2022 Sep 7. [PubMed:36084673 ]
Li J, Li J, Zhang Y, Lu H: The responses of marine anammox bacteria-based microbiome to multi-antibiotic stress in mariculture wastewater treatment. Water Res. 2022 Oct 1;224:119050. doi: 10.1016/j.watres.2022.119050. Epub 2022 Sep 3. [PubMed:36084441 ]
Lacasta D, Ruiz H, Ortin A, Villanueva-Saz S, Estrada-Pena A, Gonzalez JM, Ramos JJ, Ferrer LM, Benito AA, Labanda R, Malo C, Verde MT, Fernandez A, Ruiz de Arcaute M: Comparative Study of the Use of Doxycycline and Oxytetracycline to Treat Anaplasmosis in Fattening Lambs. Animals (Basel). 2022 Sep 2;12(17):2279. doi: 10.3390/ani12172279. [PubMed:36077999 ]
Tang T, Chen Y, Du Y, Yao B, Liu M: Effects of functional modules and bacterial clusters response on transmission performance of antibiotic resistance genes under antibiotic stress during anaerobic digestion of livestock wastewater. J Hazard Mater. 2023 Jan 5;441:129870. doi: 10.1016/j.jhazmat.2022.129870. Epub 2022 Aug 30. [PubMed:36063716 ]
Jiang H, Qi Z, Wang Z: Electrochemical-enhanced Fe(3)O(4)/biochar activates peroxymonosulfate (E/nano-Fe(3)O(4)/BC/PMS) for degradation of oxytetracycline. Chemosphere. 2022 Dec;308(Pt 1):136148. doi: 10.1016/j.chemosphere.2022.136148. Epub 2022 Aug 29. [PubMed:36049640 ]
Zhang C, Xie X, Feng S, Lei W, Xia M, Wang F, Wang H: Sensitive fluorescent detection and micromechanism of Mn-doped CuS probe for oxytetracycline hydrochloride. Spectrochim Acta A Mol Biomol Spectrosc. 2023 Jan 5;284:121768. doi: 10.1016/j.saa.2022.121768. Epub 2022 Aug 24. [PubMed:36049299 ]
Wang P, Wang J, Zhu Y, Shi R, Wang D, Yang P: Interface Nanoarchitectonics of TiO(2)/g-C(3)N(4) 2D/2D Heterostructures for Enhanced Antibiotic Degradation and Cr(VI) Reduction. Langmuir. 2022 Sep 13;38(36):11068-11079. doi: 10.1021/acs.langmuir.2c01711. Epub 2022 Aug 31. [PubMed:36044677 ]
Bahekar VS, Gonuguntla HN, Sarangi LN, Manasa G, Chandaka KD, Rana SK, Prasad A, Surendra KSNL, Ponnanna NM, Sharma GK: Detection and genetic characterization indicates circulation of a possible new Theileria species (Theileria sp. Yokoyama) in India. Vet Parasitol Reg Stud Reports. 2022 Sep;34:100765. doi: 10.1016/j.vprsr.2022.100765. Epub 2022 Jul 28. [PubMed:36041800 ]
Rutkoski CF, Grott SC, Israel NG, Carneiro FE, de Campos Guerreiro F, Santos S, Horn PA, Trentini AA, Barbosa da Silva E, Coelho de Albuquerque CA, Alves TC, Alves de Almeida E: Hepatic and blood alterations in Lithobates catesbeianus tadpoles exposed to sulfamethoxazole and oxytetracycline. Chemosphere. 2022 Nov;307(Pt 4):136215. doi: 10.1016/j.chemosphere.2022.136215. Epub 2022 Aug 27. [PubMed:36041517 ]
LOTUS database [Link]

Showing NP-Card for (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid (NP0321897)

MOL for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D MOL for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D SDF for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D-SDF for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

PDB for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D PDB for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

SMILES for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

INCHI for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

Structure for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)

3D Structure for NP0321897 ((4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid)