NP-MRD: Showing NP-Card for (4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid (NP0181535)

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Record Information

Version

2.0

Created at

2022-09-03 20:03:52 UTC

Updated at

2022-09-03 20:03:52 UTC

NP-MRD ID

NP0181535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid

Description

Tigecycline, also known as way-gar-936 or GAR 936, 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. Tetracycline in which the hydroxy group at position 5 and the methyl group at position 6 are replaced by hydrogen, and with a dimethylamino substituent and an (N-tert-butylglycyl)amino substituent at positions 7 and 9, respectively. Tigecycline is a drug which is used for the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by escherichia coli, enterococcus faecalis (vancomycin-susceptible isolates only), staphylococcus aureus (methicillin-susceptible and -resistant isolates), streptococcus agalactiae, streptococcus anginosus grp (includes s. Anginosus, s. Intermedius, and s. Constellatus), streptococcus pyogenes and bacteroides fragilis. Complicated intra-abdominal infections caused by citrobacter freundii, enterobacter cloacae, escherichia coli, klebsiella oxytoca, klebsiella pneumoniae, enterococcus faecalis (vancomycin-susceptible isolates only), staphylococcus aureus (methicillin-susceptible isolates only), streptococcus anginosus grp (includes s. Anginosus, s. Intermedius, and s. Constellatus), bacteroides fragilis, bacteroides thetaiotaomicron, bacteroides uniformis, bacteroides vulgatus, clostridium perfringens, and peptostreptococcus micros. Tigecycline is a very strong basic compound (based on its pKa). In humans, tigecycline is involved in tigecycline action pathway. A glycylcycline antibiotic, it has activity against a broad range of Gram-positive and Gram-negative bacteria, including tetracycline-resistant organisms. (4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid is found in Apis cerana. (4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid was first documented in 2005 (PMID: 16105562). It is used for the intravenous treatment of complicated skin and skin structure infections caused by susceptible organisms (PMID: 16790575) (PMID: 16863487) (PMID: 17194827) (PMID: 17210772).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231214462D          
 
 44 47  0  0  1  0            999 V2000
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 19 20  1  0  0  0  0
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  2 19  1  0  0  0  0
 42 43  1  0  0  0  0
  5  4  2  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

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  3 47  1  0
  3 48  1  0
M  END

 
  Mrv0541 02231214462D          
 
 44 47  0  0  1  0            999 V2000
   13.2848  -10.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2848  -11.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0019  -11.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0019   -9.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7150  -10.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7116  -11.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4253  -11.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4323   -9.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1460  -10.3537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1799  -11.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8486  -11.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8634   -9.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5692  -10.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5574  -11.1897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2650  -11.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9843  -11.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9962  -10.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2886   -9.9632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5693  -11.5843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8578  -11.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1425  -11.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4268  -11.1747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7115  -11.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8573  -10.3484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7175   -9.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6938  -11.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7232  -12.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4153  -11.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3005   -9.1376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0218   -8.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5951   -8.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4237  -12.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8424  -12.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2532  -12.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0038  -12.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9956  -11.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2895  -12.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1151  -12.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5495  -12.0112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5620   -9.5387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1389   -9.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0354   -9.1072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7469   -8.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3159   -8.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0  0  0  0
  4  1  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1  2  2  0  0  0  0
 22 23  1  0  0  0  0
  9 10  1  0  0  0  0
 20 24  2  0  0  0  0
 10 11  2  0  0  0  0
 17 25  1  0  0  0  0
 11 14  1  0  0  0  0
 16 26  1  0  0  0  0
 13 12  1  0  0  0  0
 26 27  2  0  0  0  0
 12  9  1  0  0  0  0
 26 28  1  0  0  0  0
  2  3  1  0  0  0  0
 18 29  1  6  0  0  0
  3  6  2  0  0  0  0
 29 30  1  0  0  0  0
  5  6  1  0  0  0  0
 29 31  1  0  0  0  0
  6  7  1  0  0  0  0
  7 32  2  0  0  0  0
  7 10  1  0  0  0  0
 11 33  1  0  0  0  0
  9  8  1  0  0  0  0
 15 34  2  0  0  0  0
 13 14  1  0  0  0  0
  3 35  1  0  0  0  0
 14 15  1  0  0  0  0
 23 36  1  0  0  0  0
 15 16  1  0  0  0  0
 23 37  1  0  0  0  0
 16 17  2  0  0  0  0
 23 38  1  0  0  0  0
 17 18  1  0  0  0  0
 14 39  1  6  0  0  0
 18 13  1  0  0  0  0
 13 40  1  6  0  0  0
  8  5  1  0  0  0  0
  9 41  1  6  0  0  0
  4 42  1  0  0  0  0
  2 19  1  0  0  0  0
 42 43  1  0  0  0  0
  5  4  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC3=C(C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

> <INCHI_KEY>
FPZLLRFZJZRHSY-HJYUBDRYSA-N

> <FORMULA>
C29H39N5O8

> <MOLECULAR_WEIGHT>
585.6487

> <EXACT_MASS>
585.279863249

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
61.77099990875321

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
-5.147120985493273

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.017413502398503

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.25205672085714514

> <JCHEM_PKA_STRONGEST_BASIC>
8.761190986995604

> <JCHEM_POLAR_SURFACE_AREA>
205.75999999999996

> <JCHEM_REFRACTIVITY>
159.34309999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tigecycline

> <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      24.798 -19.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.798 -20.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.137 -21.623   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.137 -18.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.468 -19.316   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.462 -20.857   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.794 -21.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.807 -18.547   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.139 -19.327   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.202 -20.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.451 -21.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.478 -18.566   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.796 -19.351   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.774 -20.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.095 -21.671   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.437 -20.926   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.460 -19.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.139 -18.598   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      23.463 -21.624   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      22.135 -20.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.799 -21.625   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      19.463 -20.859   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      18.128 -21.627   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.134 -19.317   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      36.806 -18.634   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      36.762 -21.711   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      36.817 -23.252   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      38.109 -20.964   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      34.161 -17.057   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      35.507 -16.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      32.844 -16.271   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      28.791 -23.170   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      31.439 -23.182   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      34.073 -23.212   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      26.140 -23.164   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.792 -20.861   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.340 -22.955   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.882 -22.955   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      32.759 -22.421   0.000  0.00  0.00           O+0
HETATM   40  H   UNK     0      32.782 -17.806   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      30.126 -17.782   0.000  0.00  0.00           H+0
HETATM   42  N   UNK     0      26.199 -17.000   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      27.528 -16.221   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      24.856 -16.246   0.000  0.00  0.00           C+0
CONECT    1    4    2                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    6   35                                                  
CONECT    4    1   42    5                                                  
CONECT    5    6    8    4                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6   32   10                                                  
CONECT    8    9    5                                                       
CONECT    9   10   12    8   41                                             
CONECT   10    9   11    7                                                  
CONECT   11   10   14   33                                                  
CONECT   12   13    9                                                       
CONECT   13   12   14   18   40                                             
CONECT   14   11   13   15   39                                             
CONECT   15   34   14   16                                                  
CONECT   16   26   15   17                                                  
CONECT   17   25   16   18                                                  
CONECT   18   29   17   13                                                  
CONECT   19   20    2                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   36   37   38                                             
CONECT   24   20                                                            
CONECT   25   17                                                            
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   18   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    7                                                            
CONECT   33   11                                                            
CONECT   34   15                                                            
CONECT   35    3                                                            
CONECT   36   23                                                            
CONECT   37   23                                                            
CONECT   38   23                                                            
CONECT   39   14                                                            
CONECT   40   13                                                            
CONECT   41    9                                                            
CONECT   42    4   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
(4S,4AS,5ar,12as)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide	ChEBI
GAR 936	Kegg
WAY-gar-936	Kegg
Tygacil	Kegg
GAR-936	HMDB
GAR-936,tigecycline	HMDB

Chemical Formula

C₂₉H₃₉N₅O₈

Average Mass

585.6487 Da

Monoisotopic Mass

585.27986 Da

IUPAC Name

(4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Traditional Name

tigecycline

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C(C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2)N(C)C

InChI Identifier

InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

InChI Key

FPZLLRFZJZRHSY-HJYUBDRYSA-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
Apis cerana	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
Tetracene
Naphthacene
Anthracene carboxylic acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Tetralin
Tertiary aliphatic/aromatic amine
Dialkylarylamine
N-arylamide
Aryl ketone
Aralkylamine
Cyclohexenone
Benzenoid
Tertiary alcohol
Vinylogous acid
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Ketone
Primary carboxylic acid amide
Secondary amine
Carboxylic acid derivative
Secondary aliphatic amine
Enol
Polyol
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tetracyclines (CHEBI:149836 )

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	0.66	ALOGPS
logP	-5.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	0.25	ChemAxon
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	205.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	159.34 m³·mol⁻¹	ChemAxon
Polarizability	61.77 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0014700

DrugBank ID

DB00560

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10482314

KEGG Compound ID

C12012

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tigecycline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

149836

Good Scents ID

Not Available

References

General References

Kasbekar N: Tigecycline: a new glycylcycline antimicrobial agent. Am J Health Syst Pharm. 2006 Jul 1;63(13):1235-43. doi: 10.2146/ajhp050487. [PubMed:16790575 ]
Rose WE, Rybak MJ: Tigecycline: first of a new class of antimicrobial agents. Pharmacotherapy. 2006 Aug;26(8):1099-110. doi: 10.1592/phco.26.8.1099. [PubMed:16863487 ]
Sader HS, Jones RN, Stilwell MG, Dowzicky MJ, Fritsche TR: Tigecycline activity tested against 26,474 bloodstream infection isolates: a collection from 6 continents. Diagn Microbiol Infect Dis. 2005 Jul;52(3):181-6. doi: 10.1016/j.diagmicrobio.2005.05.005. [PubMed:16105562 ]
Cercenado E, Marin M, Sanchez-Martinez M, Cuevas O, Martinez-Alarcon J, Bouza E: In vitro activities of tigecycline and eight other antimicrobials against different Nocardia species identified by molecular methods. Antimicrob Agents Chemother. 2007 Mar;51(3):1102-4. doi: 10.1128/AAC.01102-06. Epub 2006 Dec 28. [PubMed:17194827 ]
Izdebski R, Sadowy E, Fiett J, Grzesiowski P, Gniadkowski M, Hryniewicz W: Clonal diversity and resistance mechanisms in tetracycline-nonsusceptible Streptococcus pneumoniae isolates in Poland. Antimicrob Agents Chemother. 2007 Apr;51(4):1155-63. doi: 10.1128/AAC.01384-06. Epub 2007 Jan 8. [PubMed:17210772 ]
LOTUS database [Link]

Showing NP-Card for (4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid (NP0181535)

MOL for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

3D MOL for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

3D SDF for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

3D-SDF for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

PDB for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

3D PDB for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

SMILES for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

INCHI for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

Structure for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)

3D Structure for NP0181535 ((4s,4as,5ar,12as)-9-{[2-(tert-butylamino)-1-hydroxyethylidene]amino}-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboximidic acid)