NP-MRD: Showing NP-Card for FK-506 (NP0137595)

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Record Information

Version

2.0

Created at

2022-05-30 16:57:14 UTC

Updated at

2022-05-30 16:57:14 UTC

NP-MRD ID

NP0137595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

FK-506

Description

Tacrolimus, also known as FK 506 or prograf, belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. Thus, tacrolimus is considered to be a macrolide lipid molecule. A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. Tacrolimus is a drug which is used for use after allogenic organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It was given fda approval in 1994 for use in liver transplantation. Since then, this indication has expanded to kidney, heart, small bowel, pancreas, lung, trachea, skin, cornea, and limb transplants. It has also been used in a topical preparation in the treatment of severe atopic dermatitis. Tacrolimus is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Tacrolimus may be a unique E. Coli metabolite. FK-506 is found in Streptomyces clavuligerus, Streptomyces durmitorensis, Streptomyces hygroscopicus, Streptomyces kanamyceticus, Streptomyces tacrolimicus and Streptomyces tsukubensis. In humans, tacrolimus is involved in t cell receptor signaling pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231215032D          

 57 60  0  0  1  0            999 V2000
   11.8740   -7.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8740   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1658   -6.4995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1658   -5.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4158   -5.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7076   -5.6662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7076   -6.4995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4158   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9993   -6.9162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9993   -5.2497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911   -6.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5824   -8.1661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1658   -8.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2907   -7.7494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9989   -8.1661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9989   -8.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7492  -14.2489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   12.0407  -12.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9158  -11.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9158  -10.4991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0826  -10.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3325   -9.7910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9158   -9.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6660   -9.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1656  -11.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0827  -11.9676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448  -13.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1657   -9.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5824  -10.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5824   -9.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2907   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7223   -7.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9984  -10.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  1  0  0  0
  6 10  1  6  0  0  0
  9 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  6  0  0  0
 28 33  1  1  0  0  0
 26 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 31 37  1  1  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
 41 40  1  0  0  0  0
 42 40  1  1  0  0  0
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 41 45  1  0  0  0  0
 39 40  1  0  0  0  0
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 12 51  1  6  0  0  0
 14 52  1  6  0  0  0
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 17 54  2  0  0  0  0
 18 55  1  6  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
M  END

     RDKit          3D

126129  0  0  0  0  0  0  0  0999 V2000
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M  END

 
  Mrv0541 02231215032D          

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  3  8  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0137595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]1C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1

> <INCHI_KEY>
QJJXYPPXXYFBGM-LFZNUXCKSA-N

> <FORMULA>
C44H69NO12

> <MOLECULAR_WEIGHT>
804.0182

> <EXACT_MASS>
803.481976677

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
87.41459547535347

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
5.594120193333335

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.071408376193439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.955600393207165

> <JCHEM_PKA_STRONGEST_BASIC>
-2.937095707399786

> <JCHEM_POLAR_SURFACE_AREA>
178.35999999999996

> <JCHEM_REFRACTIVITY>
215.62030000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tacrolimus

> <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      22.165 -14.466   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.165 -12.910   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.843 -12.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.843 -10.577   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.443  -9.799   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.121 -10.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.121 -12.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.443 -12.910   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.799 -12.910   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.799  -9.799   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.477 -12.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.487 -15.243   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.843 -15.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.809 -14.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.131 -15.243   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.131 -16.799   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.609 -17.421   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.309 -18.899   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.531 -20.299   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.131 -21.076   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.809 -20.299   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.131 -22.632   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.809 -23.409   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.487 -22.632   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.587 -24.732   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.498 -25.898   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.021 -25.509   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.932 -26.598   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.454 -26.209   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.065 -24.732   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.154 -23.643   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      22.632 -24.032   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      22.320 -28.076   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      24.887 -27.376   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      26.365 -27.842   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.232 -29.164   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      22.476 -22.943   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      20.376 -22.320   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.154 -20.921   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      20.376 -19.598   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      18.821 -19.598   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      21.154 -18.276   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.376 -16.876   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.821 -16.876   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.043 -18.199   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      22.709 -20.902   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      18.821 -22.340   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      18.564 -24.326   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.709 -18.276   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      23.487 -19.623   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      23.487 -16.929   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      24.809 -12.910   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      27.482 -14.471   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      28.762 -16.608   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      29.864 -18.949   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      30.673 -17.647   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      32.197 -17.619   0.000  0.00  0.00           C+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   11                                                       
CONECT   10    6                                                            
CONECT   11    9                                                            
CONECT   12    1   14   51                                                  
CONECT   13    1                                                            
CONECT   14   12   15   52                                                  
CONECT   15   14   16   53                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   54                                                  
CONECT   18   17   19   55                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   48                                                  
CONECT   31   30   32   37   38                                             
CONECT   32   31   27                                                       
CONECT   33   28   36                                                       
CONECT   34   26   35                                                       
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   31                                                            
CONECT   38   31   39   47                                                  
CONECT   39   38   40   46                                                  
CONECT   40   41   42   39                                                  
CONECT   41   40   45                                                       
CONECT   42   40   43   49                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   41                                                       
CONECT   46   39                                                            
CONECT   47   38                                                            
CONECT   48   30                                                            
CONECT   49   42   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   12                                                       
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   17                                                            
CONECT   55   18   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

View in JSmol

Synonyms

Value	Source
(-)-FK 506	ChEBI
8-DEETHYL-8-[but-3-enyl]-ascomycin	ChEBI
FK 506	ChEBI
FK506	ChEBI
Prograf	ChEBI
Tacrolimus anhydrous	ChEBI
FK-506	HMDB
FK5	HMDB
K506	HMDB
Tacarolimus	HMDB
Tacrolimus hydrate	HMDB
Anhydrous tacrolimus	MeSH
Tacrolimus, anhydrous	MeSH
Anhydrous, tacrolimus	MeSH
Fujisawa brand OF tacrolimus	MeSH
Prograft	MeSH
Cilag brand OF tacrolimus	MeSH
Janssen brand OF tacrolimus	MeSH

Chemical Formula

C₄₄H₆₉NO₁₂

Average Mass

804.0182 Da

Monoisotopic Mass

803.48198 Da

IUPAC Name

(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone

Traditional Name

tacrolimus

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]1C)OC

InChI Identifier

InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1

InChI Key

QJJXYPPXXYFBGM-LFZNUXCKSA-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 clavuligerus	LOTUS Database	35616633
Streptomyces durmitorensis	LOTUS Database	35616633
Streptomyces hygroscopicus	LOTUS Database	35616633
Streptomyces kanamyceticus	LOTUS Database	35616633
Streptomyces tacrolimicus	LOTUS Database	35616633
Streptomyces tsukubensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Alpha-amino acid ester
Macrolide
Alpha-amino acid or derivatives
Cyclohexanol
Oxane
Piperidine
Cyclic alcohol
Tertiary carboxylic acid amide
Cyclic ketone
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Hemiacetal
Ketone
Lactam
Lactone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:61049 )
Macrolides and lactone polyketides (C01375 )
Macrolides and lactone polyketides (LMPK04000003 )

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	3.19	ALOGPS
logP	5.59	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	178.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	215.62 m³·mol⁻¹	ChemAxon
Polarizability	87.41 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

Not Available

DrugBank ID

DB00864

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01375

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tacrolimus

METLIN ID

Not Available

PubChem Compound

445643

PDB ID

Not Available

ChEBI ID

61049

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for FK-506 (NP0137595)

MOL for NP0137595 (FK-506)

3D MOL for NP0137595 (FK-506)

3D SDF for NP0137595 (FK-506)

3D-SDF for NP0137595 (FK-506)

PDB for NP0137595 (FK-506)

3D PDB for NP0137595 (FK-506)

SMILES for NP0137595 (FK-506)

INCHI for NP0137595 (FK-506)

Structure for NP0137595 (FK-506)

3D Structure for NP0137595 (FK-506)