Hmdb loader

Showing metabocard for Tacrolimus (HMDB0015002)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4)transporters (1) Show 5 proteinsXML
enzymes (4)transporters (1) Show 5 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:49 UTC
HMDB IDHMDB0015002
Secondary Accession Numbers
  • HMDB15002
Metabolite Identification
Common NameTacrolimus
DescriptionTacrolimus (also FK-506 or Fujimycin) is an immunosuppressive drug whose main use is after organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It is also used in a topical preparation in the treatment of severe atopic dermatitis, severe refractory uveitis after bone marrow transplants, and the skin condition vitiligo. It was discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. Tacrolimus is chemically known as a macrolide. It reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP-12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex interacts with and inhibits calcineurin thus inhibiting both T-lymphocyte signal transduction and IL-2 transcription.
Structure
Data?1582753246
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015002 (Tacrolimus)


  Mrv1652307191923542D          

 72 75  0  0  1  0            999 V2000
    1.9898   -2.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954   -2.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5409    0.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 39 71  1  1  0  0  0
 40 72  1  1  0  0  0
M  END
Download

3D MOL for HMDB0015002 (Tacrolimus)

HMDB0015002
     RDKit          3D
Tacrolimus
126129  0  0  0  0  0  0  0  0999 V2000
    1.6254    6.0313    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    6.1667   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    5.0762   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    3.8097   -0.9589 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6395    4.0433   -1.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363    3.1641   -1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629    3.0882   -3.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    2.3068   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644    2.3060   -0.4742 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1055    3.6381   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.1567   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1914    0.0645   -0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2644   -2.0499   -0.2074 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0015002 (Tacrolimus)


  Mrv1652307191923542D          

 72 75  0  0  1  0            999 V2000
    1.9898   -2.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954   -2.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6752   -1.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9552    2.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409    0.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7123   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945    1.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8302    1.7649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3558   -5.1168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1472    3.0493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7701   -2.6001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0015002

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)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-LJIGMGMYSA-N

> <FORMULA>
C44H69NO12

> <MOLECULAR_WEIGHT>
804.0182

> <EXACT_MASS>
803.481976677

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
88.1362752348501

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S,12S,13R,14S,17R,18Z,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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
5.594120193333334

> <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>
178.35999999999993

> <JCHEM_REFRACTIVITY>
215.62030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,12S,13R,14S,17R,18Z,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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015002 (Tacrolimus)

HMDB0015002
     RDKit          3D
Tacrolimus
126129  0  0  0  0  0  0  0  0999 V2000
    1.6254    6.0313    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    6.1667   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3503    5.0762   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    3.8097   -0.9589 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6395    4.0433   -1.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363    3.1641   -1.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629    3.0882   -3.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    2.3068   -0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644    2.3060   -0.4742 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1055    3.6381   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.1567   -1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9302    0.3619   -0.0222 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1914    0.0645   -0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1840    0.7792    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1624   -0.8222    0.4044 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2569   -1.1522   -0.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644   -2.0499   -0.2074 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5447   -1.5510    0.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4289   -2.3456   -1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -1.6582   -2.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3588   -3.3120   -1.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -4.1974   -2.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -3.4364   -0.7247 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -4.7752   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721   -5.1704   -0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4604   -4.0775   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069   -2.8224   -0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229   -2.3631   -0.3763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6575   -1.9282    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -2.8206    1.8685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -0.6586    1.3517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    0.1173    1.5978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3711   -0.5059    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5737   -1.7182    2.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4450   -0.1452    0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7629   -0.8455    1.0339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1932   -1.5010   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4646   -0.4220   -1.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6980    0.3096   -0.8410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7906   -0.2852   -1.4926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9823    0.2836    0.6308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5950    1.5068    0.9414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8752    1.3291    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7732    0.1667    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    1.4195    0.7880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9398    2.4543    1.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604    1.2215   -0.6848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7584    2.2062   -1.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584    1.4550   -1.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240    2.8521   -1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395    3.2169   -2.7141 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9769   -3.3098    0.2692 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0251   -4.3405    0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9991   -3.0397    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0097   -1.9797    0.7831 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8610   -1.7001    1.8184 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1306   -2.2761    1.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165    5.1361    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    6.8859    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0800    7.1548   -0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    4.8986   -0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067    5.4739   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6445    3.4392    0.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011    5.0072   -2.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9452    2.1325   -3.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6656    3.0657   -4.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019    3.9857   -3.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4414    2.5955    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    1.2375   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442    2.1793    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6847    3.5947   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3326    4.4193   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8475    3.8908   -0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500    1.4674   -1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4400    0.4857   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0534    1.0769    0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1919    0.6051    1.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9867    1.8660    0.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1727    0.5396   -0.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4991   -0.6135    1.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7771   -1.9818    1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247   -4.8219    0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4818   -5.5724   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -6.0782    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127   -5.4340   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5079   -4.3757   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -3.9193    1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9886   -3.1115   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8787   -2.0610   -0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.4577   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6367   -1.9933    3.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5567   -2.0001    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

PDB for HMDB0015002 (Tacrolimus)

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0       3.714  -4.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.231  -4.466   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.110  -1.591   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.327  -2.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.383   5.380   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.343   0.682   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.263  -8.713   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.923   2.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.835   5.166   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.222  -5.068   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.899   2.671   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.415   4.133   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.246  -3.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.169   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.255  -6.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.739  -7.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.907   4.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.632  -1.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.738  -3.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.606   0.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.795  -3.703   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.851   4.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.787  -5.477   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.295  -1.618   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.230  -3.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.294  -0.956   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.819  -2.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.359   4.230   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.827  -0.780   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.279  -5.165   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.763  -2.456   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.367   1.833   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.247  -8.089   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.803  -1.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.271  -2.768   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.271  -6.939   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.136   0.721   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.827   3.392   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.335  -1.091   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.311   1.930   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.351   2.456   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.375   3.606   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.875   1.521   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.843   2.768   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      10.883   3.294   0.000  0.00  0.00           N+0
HETATM   46  O   UNK     0      13.731  -9.551   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      10.287  -3.392   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.755  -4.230   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       8.835   0.994   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       8.891   5.068   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      14.380   1.849   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       7.867   3.918   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      15.779  -7.251   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       2.460   2.104   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       2.319   3.704   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      13.359   0.059   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       5.819   1.618   0.000  0.00  0.00           O+0
HETATM   58  H   UNK     0       5.693  -4.815   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      10.271  -3.926   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.222  -2.495   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.875   5.692   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       9.319  -0.468   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      10.771  -4.854   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.451  -3.964   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      12.573   2.790   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      12.223  -9.239   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.779  -3.080   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      15.295  -5.789   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.787   1.463   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.343   4.854   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      11.311  -2.241   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.018   2.767   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   53                                                            
CONECT    8   54                                                            
CONECT    9   55                                                            
CONECT   10    1   13                                                       
CONECT   11   12   14                                                       
CONECT   12   11   17                                                       
CONECT   13   10   31                                                       
CONECT   14   11   32                                                       
CONECT   15   16   30                                                       
CONECT   16   15   33                                                       
CONECT   17   12   45                                                       
CONECT   18   25   26                                                       
CONECT   19   25   31   58                                                  
CONECT   20   26   37                                                       
CONECT   21   27   30   59                                                  
CONECT   22   28   38                                                       
CONECT   23   30   36                                                       
CONECT   24   34   35                                                       
CONECT   25    2   18   19                                                  
CONECT   26    3   18   20   60                                             
CONECT   27    4   21   39                                                  
CONECT   28    5   22   44   61                                             
CONECT   29    6   34   39   62                                             
CONECT   30   15   21   23   63                                             
CONECT   31   13   19   35   64                                             
CONECT   32   14   43   45   65                                             
CONECT   33   16   36   46   66                                             
CONECT   34   24   29   47   67                                             
CONECT   35   24   31   48                                                  
CONECT   36   23   33   53   68                                             
CONECT   37   20   40   54   69                                             
CONECT   38   22   40   55   70                                             
CONECT   39   27   29   56   71                                             
CONECT   40   37   38   57   72                                             
CONECT   41   42   44   49                                                  
CONECT   42   41   45   50                                                  
CONECT   43   32   51   56                                                  
CONECT   44   28   41   52   57                                             
CONECT   45   17   32   42                                                  
CONECT   46   33                                                            
CONECT   47   34                                                            
CONECT   48   35                                                            
CONECT   49   41                                                            
CONECT   50   42                                                            
CONECT   51   43                                                            
CONECT   52   44                                                            
CONECT   53    7   36                                                       
CONECT   54    8   37                                                       
CONECT   55    9   38                                                       
CONECT   56   39   43                                                       
CONECT   57   40   44                                                       
CONECT   58   19                                                            
CONECT   59   21                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   34                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
CONECT   71   39                                                            
CONECT   72   40                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END
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3D PDB for HMDB0015002 (Tacrolimus)

COMPND    HMDB0015002
HETATM    1  C1  UNL     1       1.625   6.031   0.312  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.400   6.167  -0.142  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.350   5.076  -0.798  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.453   3.810  -0.959  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.640   4.043  -1.789  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.636   3.164  -1.929  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.363   3.088  -3.235  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.980   2.307  -0.794  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.464   2.306  -0.474  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.106   3.638  -0.804  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.175   1.157  -1.120  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.930   0.362  -0.022  1.00  0.00           C  
HETATM   13  O1  UNL     1       7.191   0.064  -0.450  1.00  0.00           O  
HETATM   14  C13 UNL     1       8.184   0.779   0.221  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.162  -0.822   0.404  1.00  0.00           C  
HETATM   16  O2  UNL     1       4.257  -1.152  -0.610  1.00  0.00           O  
HETATM   17  C15 UNL     1       3.264  -2.050  -0.207  1.00  0.00           C  
HETATM   18  O3  UNL     1       2.545  -1.551   0.873  1.00  0.00           O  
HETATM   19  C16 UNL     1       2.429  -2.346  -1.386  1.00  0.00           C  
HETATM   20  O4  UNL     1       2.679  -1.658  -2.453  1.00  0.00           O  
HETATM   21  C17 UNL     1       1.359  -3.312  -1.506  1.00  0.00           C  
HETATM   22  O5  UNL     1       1.465  -4.197  -2.457  1.00  0.00           O  
HETATM   23  N1  UNL     1       0.189  -3.436  -0.725  1.00  0.00           N  
HETATM   24  C18 UNL     1      -0.147  -4.775  -0.245  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.572  -5.170  -0.540  1.00  0.00           C  
HETATM   26  C20 UNL     1      -2.460  -4.077  -0.029  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.107  -2.822  -0.792  1.00  0.00           C  
HETATM   28  C22 UNL     1      -0.723  -2.363  -0.376  1.00  0.00           C  
HETATM   29  C23 UNL     1      -0.657  -1.928   1.041  1.00  0.00           C  
HETATM   30  O6  UNL     1      -0.313  -2.821   1.869  1.00  0.00           O  
HETATM   31  O7  UNL     1      -0.955  -0.659   1.352  1.00  0.00           O  
HETATM   32  C24 UNL     1      -2.054   0.117   1.598  1.00  0.00           C  
HETATM   33  C25 UNL     1      -3.371  -0.506   1.625  1.00  0.00           C  
HETATM   34  C26 UNL     1      -3.574  -1.718   2.508  1.00  0.00           C  
HETATM   35  C27 UNL     1      -4.445  -0.145   0.942  1.00  0.00           C  
HETATM   36  C28 UNL     1      -5.763  -0.846   1.034  1.00  0.00           C  
HETATM   37  C29 UNL     1      -6.193  -1.501  -0.232  1.00  0.00           C  
HETATM   38  C30 UNL     1      -6.465  -0.422  -1.259  1.00  0.00           C  
HETATM   39  C31 UNL     1      -7.698   0.310  -0.841  1.00  0.00           C  
HETATM   40  O8  UNL     1      -8.791  -0.285  -1.493  1.00  0.00           O  
HETATM   41  C32 UNL     1      -7.982   0.284   0.631  1.00  0.00           C  
HETATM   42  O9  UNL     1      -8.595   1.507   0.941  1.00  0.00           O  
HETATM   43  C33 UNL     1      -9.875   1.329   1.460  1.00  0.00           C  
HETATM   44  C34 UNL     1      -6.773   0.167   1.500  1.00  0.00           C  
HETATM   45  C35 UNL     1      -1.981   1.420   0.788  1.00  0.00           C  
HETATM   46  C36 UNL     1      -2.940   2.454   1.292  1.00  0.00           C  
HETATM   47  C37 UNL     1      -1.960   1.221  -0.685  1.00  0.00           C  
HETATM   48  O10 UNL     1      -2.758   2.206  -1.309  1.00  0.00           O  
HETATM   49  C38 UNL     1      -0.558   1.455  -1.280  1.00  0.00           C  
HETATM   50  C39 UNL     1      -0.424   2.852  -1.719  1.00  0.00           C  
HETATM   51  O11 UNL     1      -1.040   3.217  -2.714  1.00  0.00           O  
HETATM   52  C40 UNL     1       3.977  -3.310   0.269  1.00  0.00           C  
HETATM   53  C41 UNL     1       3.025  -4.341   0.811  1.00  0.00           C  
HETATM   54  C42 UNL     1       4.999  -3.040   1.320  1.00  0.00           C  
HETATM   55  C43 UNL     1       6.010  -1.980   0.783  1.00  0.00           C  
HETATM   56  O12 UNL     1       6.861  -1.700   1.818  1.00  0.00           O  
HETATM   57  C44 UNL     1       8.131  -2.276   1.662  1.00  0.00           C  
HETATM   58  H1  UNL     1       2.216   5.136   0.264  1.00  0.00           H  
HETATM   59  H2  UNL     1       2.112   6.886   0.783  1.00  0.00           H  
HETATM   60  H3  UNL     1      -0.080   7.155  -0.018  1.00  0.00           H  
HETATM   61  H4  UNL     1      -1.282   4.899  -0.199  1.00  0.00           H  
HETATM   62  H5  UNL     1      -0.707   5.474  -1.771  1.00  0.00           H  
HETATM   63  H6  UNL     1       0.645   3.439   0.062  1.00  0.00           H  
HETATM   64  H7  UNL     1       1.701   5.007  -2.329  1.00  0.00           H  
HETATM   65  H8  UNL     1       3.945   2.133  -3.308  1.00  0.00           H  
HETATM   66  H9  UNL     1       2.666   3.066  -4.110  1.00  0.00           H  
HETATM   67  H10 UNL     1       4.002   3.986  -3.413  1.00  0.00           H  
HETATM   68  H11 UNL     1       2.441   2.596   0.104  1.00  0.00           H  
HETATM   69  H12 UNL     1       2.757   1.238  -1.089  1.00  0.00           H  
HETATM   70  H13 UNL     1       4.544   2.179   0.623  1.00  0.00           H  
HETATM   71  H14 UNL     1       5.685   3.595  -1.749  1.00  0.00           H  
HETATM   72  H15 UNL     1       4.333   4.419  -0.787  1.00  0.00           H  
HETATM   73  H16 UNL     1       5.848   3.891  -0.017  1.00  0.00           H  
HETATM   74  H17 UNL     1       5.950   1.467  -1.840  1.00  0.00           H  
HETATM   75  H18 UNL     1       4.440   0.486  -1.556  1.00  0.00           H  
HETATM   76  H19 UNL     1       6.053   1.077   0.849  1.00  0.00           H  
HETATM   77  H20 UNL     1       8.192   0.605   1.300  1.00  0.00           H  
HETATM   78  H21 UNL     1       7.987   1.866   0.026  1.00  0.00           H  
HETATM   79  H22 UNL     1       9.173   0.540  -0.173  1.00  0.00           H  
HETATM   80  H23 UNL     1       4.499  -0.613   1.299  1.00  0.00           H  
HETATM   81  H24 UNL     1       2.777  -1.982   1.721  1.00  0.00           H  
HETATM   82  H25 UNL     1       0.025  -4.822   0.825  1.00  0.00           H  
HETATM   83  H26 UNL     1       0.482  -5.572  -0.700  1.00  0.00           H  
HETATM   84  H27 UNL     1      -1.776  -6.078   0.081  1.00  0.00           H  
HETATM   85  H28 UNL     1      -1.713  -5.434  -1.589  1.00  0.00           H  
HETATM   86  H29 UNL     1      -3.508  -4.376  -0.169  1.00  0.00           H  
HETATM   87  H30 UNL     1      -2.193  -3.919   1.038  1.00  0.00           H  
HETATM   88  H31 UNL     1      -1.989  -3.112  -1.877  1.00  0.00           H  
HETATM   89  H32 UNL     1      -2.879  -2.061  -0.751  1.00  0.00           H  
HETATM   90  H33 UNL     1      -0.530  -1.458  -1.039  1.00  0.00           H  
HETATM   91  H34 UNL     1      -1.910   0.517   2.664  1.00  0.00           H  
HETATM   92  H35 UNL     1      -2.637  -1.993   3.029  1.00  0.00           H  
HETATM   93  H36 UNL     1      -3.940  -2.559   1.920  1.00  0.00           H  
HETATM   94  H37 UNL     1      -4.278  -1.439   3.332  1.00  0.00           H  
HETATM   95  H38 UNL     1      -4.336   0.708   0.283  1.00  0.00           H  
HETATM   96  H39 UNL     1      -5.740  -1.632   1.834  1.00  0.00           H  
HETATM   97  H40 UNL     1      -5.469  -2.249  -0.594  1.00  0.00           H  
HETATM   98  H41 UNL     1      -7.144  -2.027  -0.025  1.00  0.00           H  
HETATM   99  H42 UNL     1      -6.561  -0.907  -2.255  1.00  0.00           H  
HETATM  100  H43 UNL     1      -5.588   0.261  -1.247  1.00  0.00           H  
HETATM  101  H44 UNL     1      -7.619   1.346  -1.238  1.00  0.00           H  
HETATM  102  H45 UNL     1      -9.413   0.400  -1.844  1.00  0.00           H  
HETATM  103  H46 UNL     1      -8.722  -0.514   0.901  1.00  0.00           H  
HETATM  104  H47 UNL     1      -9.870   0.729   2.393  1.00  0.00           H  
HETATM  105  H48 UNL     1     -10.287   2.325   1.721  1.00  0.00           H  
HETATM  106  H49 UNL     1     -10.560   0.913   0.690  1.00  0.00           H  
HETATM  107  H50 UNL     1      -7.147  -0.031   2.538  1.00  0.00           H  
HETATM  108  H51 UNL     1      -6.332   1.206   1.568  1.00  0.00           H  
HETATM  109  H52 UNL     1      -0.951   1.842   1.042  1.00  0.00           H  
HETATM  110  H53 UNL     1      -2.421   3.321   1.802  1.00  0.00           H  
HETATM  111  H54 UNL     1      -3.552   2.943   0.510  1.00  0.00           H  
HETATM  112  H55 UNL     1      -3.575   2.031   2.110  1.00  0.00           H  
HETATM  113  H56 UNL     1      -2.256   0.210  -1.006  1.00  0.00           H  
HETATM  114  H57 UNL     1      -3.087   1.796  -2.148  1.00  0.00           H  
HETATM  115  H58 UNL     1       0.125   1.294  -0.420  1.00  0.00           H  
HETATM  116  H59 UNL     1      -0.392   0.727  -2.088  1.00  0.00           H  
HETATM  117  H60 UNL     1       4.532  -3.788  -0.590  1.00  0.00           H  
HETATM  118  H61 UNL     1       2.711  -5.068   0.026  1.00  0.00           H  
HETATM  119  H62 UNL     1       3.518  -4.981   1.598  1.00  0.00           H  
HETATM  120  H63 UNL     1       2.167  -3.882   1.321  1.00  0.00           H  
HETATM  121  H64 UNL     1       4.600  -2.669   2.282  1.00  0.00           H  
HETATM  122  H65 UNL     1       5.557  -3.964   1.521  1.00  0.00           H  
HETATM  123  H66 UNL     1       6.518  -2.525  -0.022  1.00  0.00           H  
HETATM  124  H67 UNL     1       7.917  -3.388   1.631  1.00  0.00           H  
HETATM  125  H68 UNL     1       8.795  -1.987   2.474  1.00  0.00           H  
HETATM  126  H69 UNL     1       8.557  -2.000   0.693  1.00  0.00           H  
CONECT    1    2    2   58   59
CONECT    2    3   60
CONECT    3    4   61   62
CONECT    4    5   50   63
CONECT    5    6    6   64
CONECT    6    7    8
CONECT    7   65   66   67
CONECT    8    9   68   69
CONECT    9   10   11   70
CONECT   10   71   72   73
CONECT   11   12   74   75
CONECT   12   13   15   76
CONECT   13   14
CONECT   14   77   78   79
CONECT   15   16   55   80
CONECT   16   17
CONECT   17   18   19   52
CONECT   18   81
CONECT   19   20   20   21
CONECT   21   22   22   23
CONECT   23   24   28
CONECT   24   25   82   83
CONECT   25   26   84   85
CONECT   26   27   86   87
CONECT   27   28   88   89
CONECT   28   29   90
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33   45   91
CONECT   33   34   35   35
CONECT   34   92   93   94
CONECT   35   36   95
CONECT   36   37   44   96
CONECT   37   38   97   98
CONECT   38   39   99  100
CONECT   39   40   41  101
CONECT   40  102
CONECT   41   42   44  103
CONECT   42   43
CONECT   43  104  105  106
CONECT   44  107  108
CONECT   45   46   47  109
CONECT   46  110  111  112
CONECT   47   48   49  113
CONECT   48  114
CONECT   49   50  115  116
CONECT   50   51   51
CONECT   52   53   54  117
CONECT   53  118  119  120
CONECT   54   55  121  122
CONECT   55   56  123
CONECT   56   57
CONECT   57  124  125  126
END
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SMILES for HMDB0015002 (Tacrolimus)

[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC
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INCHI for HMDB0015002 (Tacrolimus)

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
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Anhydrous, tacrolimusHMDB
Anhydrous tacrolimusHMDB
PrografHMDB
Tacrolimus anhydrousHMDB
Tacrolimus, anhydrousHMDB
Fujisawa brand OF tacrolimusHMDB
PrograftHMDB
Cilag brand OF tacrolimusHMDB
Janssen brand OF tacrolimusHMDB
Chemical FormulaC44H69NO12
Average Molecular Weight804.0182
Monoisotopic Molecular Weight803.481976677
IUPAC Name(1R,9S,12S,13R,14S,17R,18Z,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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone
Traditional Name(1R,9S,12S,13R,14S,17R,18Z,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[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone
CAS Registry Number104987-11-3
SMILES
[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)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 KeyQJJXYPPXXYFBGM-LJIGMGMYSA-N
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolide lactams
Sub ClassNot Available
Direct ParentMacrolide 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 FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.19ALOGPS
logP5.59ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area178.36 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity215.62 m³·mol⁻¹ChemAxon
Polarizability88.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+267.34830932474
DeepCCS[M-H]-265.62530932474
DeepCCS[M-2H]-299.65830932474
DeepCCS[M+Na]+273.67130932474
AllCCS[M+H]+272.132859911
AllCCS[M+H-H2O]+271.532859911
AllCCS[M+NH4]+272.732859911
AllCCS[M+Na]+272.932859911
AllCCS[M-H]-259.232859911
AllCCS[M+Na-2H]-266.032859911
AllCCS[M+HCOO]-273.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tacrolimus[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC4653.7Standard polar33892256
Tacrolimus[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC4743.9Standard non polar33892256
Tacrolimus[H]\C(=C(\C)[C@@]1([H])OC(=O)[C@]2([H])CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@]([H])(C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C([H])/[C@@]([H])(CC=C)C(=O)C[C@]([H])(O)[C@@]1([H])C)OC)[C@]1([H])CC[C@@]([H])(O)[C@@]([H])(C1)OC5384.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tacrolimus GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tacrolimus GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tacrolimus GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tacrolimus GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tacrolimus GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus Linear Ion Trap , negative-QTOFsplash10-0gvo-0000192300-507c8bb18631e452a4842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus Linear Ion Trap , positive-QTOFsplash10-066r-0000119030-65296f545a06c11d017b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus Linear Ion Trap , positive-QTOFsplash10-001i-0000009120-d1952a63d681e01b0eec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus 40V, Negative-QTOFsplash10-0gb9-0973261100-2ee28926fa74ad5bfbf72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus 20V, Negative-QTOFsplash10-0udi-0225271390-6837305c39f6b65c92fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tacrolimus 10V, Negative-QTOFsplash10-0udi-0220030290-ceafe80295758dda73b42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 10V, Positive-QTOFsplash10-0f79-0200001930-3416d86dc0d61354fd202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 20V, Positive-QTOFsplash10-014u-1400003900-1705b8ca1b5858186d962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 40V, Positive-QTOFsplash10-00rf-5200008900-20683c9798305f220c922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 10V, Negative-QTOFsplash10-0udi-0000000490-b536a515071aa91b3d992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 20V, Negative-QTOFsplash10-0uei-0000000920-face0da2f9f0fced4ae72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 40V, Negative-QTOFsplash10-0a4r-3000001900-75ecdc7e12ec9d9989cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 10V, Positive-QTOFsplash10-0udi-0100000950-1c5a13554e5f7c0cb19d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 20V, Positive-QTOFsplash10-0udj-0000000910-da1939239c06f39a19e52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 40V, Positive-QTOFsplash10-03di-6100001900-2b571619b8d121a404702021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 10V, Negative-QTOFsplash10-0udi-0000000490-edb714c334df2df2491b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 20V, Negative-QTOFsplash10-0udi-0000001940-b4cff31e71a4daf5e13f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tacrolimus 40V, Negative-QTOFsplash10-0nmi-2000009410-12aa8c80b0c1ed3b8a6b2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00864 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00864 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011098
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTacrolimus
METLIN IDNot Available
PubChem Compound6473866
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Liu J, Farmer JD Jr, Lane WS, Friedman J, Weissman I, Schreiber SL: Calcineurin is a common target of cyclophilin-cyclosporin A and FKBP-FK506 complexes. Cell. 1991 Aug 23;66(4):807-15. [PubMed:1715244 ]
  2. Kino T, Hatanaka H, Hashimoto M, Nishiyama M, Goto T, Okuhara M, Kohsaka M, Aoki H, Imanaka H: FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physico-chemical and biological characteristics. J Antibiot (Tokyo). 1987 Sep;40(9):1249-55. [PubMed:2445721 ]
  3. Pritchard DI: Sourcing a chemical succession for cyclosporin from parasites and human pathogens. Drug Discov Today. 2005 May 15;10(10):688-91. [PubMed:15896681 ]
  4. Hanifin JM, Paller AS, Eichenfield L, Clark RA, Korman N, Weinstein G, Caro I, Jaracz E, Rico MJ: Efficacy and safety of tacrolimus ointment treatment for up to 4 years in patients with atopic dermatitis. J Am Acad Dermatol. 2005 Aug;53(2 Suppl 2):S186-94. [PubMed:16021174 ]
  5. Fukatsu S, Fukudo M, Masuda S, Yano I, Katsura T, Ogura Y, Oike F, Takada Y, Inui K: Delayed effect of grapefruit juice on pharmacokinetics and pharmacodynamics of tacrolimus in a living-donor liver transplant recipient. Drug Metab Pharmacokinet. 2006 Apr;21(2):122-5. [PubMed:16702731 ]
  6. (). FDA label . .

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]
Enzyme Details
2. Cytochrome P450 3A5
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 3A7
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
Enzyme Details
4. Peptidyl-prolyl cis-trans isomerase FKBP1A
General function:
Involved in protein folding
Specific function:
May play a role in modulation of ryanodine receptor isoform-1 (RYR-1), a component of the calcium release channel of skeletal muscle sarcoplasmic reticulum. There are four molecules of FKBP12 per skeletal muscle RYR. PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides
Gene Name:
FKBP1A
Uniprot ID:
P62942
Molecular weight:
11950.7
References
  1. Labrande C, Velly L, Canolle B, Guillet B, Masmejean F, Nieoullon A, Pisano P: Neuroprotective effects of tacrolimus (FK506) in a model of ischemic cortical cell cultures: role of glutamate uptake and FK506 binding protein 12 kDa. Neuroscience. 2006;137(1):231-9. Epub 2005 Nov 10. [PubMed:16289353 ]
  2. Masri M, Rizk S, Barbari A, Stephan A, Kamel G, Rost M: An assay for the determination of sirolimus levels in the lymphocyte of transplant patients. Transplant Proc. 2007 May;39(4):1204-6. [PubMed:17524933 ]

Transporters

Enzyme Details
1. Multidrug resistance protein 1
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764 ]
  2. Saeki T, Ueda K, Tanigawara Y, Hori R, Komano T: Human P-glycoprotein transports cyclosporin A and FK506. J Biol Chem. 1993 Mar 25;268(9):6077-80. [PubMed:7681059 ]
  3. Wandel C, Kim RB, Kajiji S, Guengerich P, Wilkinson GR, Wood AJ: P-glycoprotein and cytochrome P-450 3A inhibition: dissociation of inhibitory potencies. Cancer Res. 1999 Aug 15;59(16):3944-8. [PubMed:10463589 ]
  4. Hashida T, Masuda S, Uemoto S, Saito H, Tanaka K, Inui K: Pharmacokinetic and prognostic significance of intestinal MDR1 expression in recipients of living-donor liver transplantation. Clin Pharmacol Ther. 2001 May;69(5):308-16. [PubMed:11371998 ]
  5. Collett A, Tanianis-Hughes J, Hallifax D, Warhurst G: Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26. [PubMed:15180340 ]
  6. Quezada CA, Garrido WX, Gonzalez-Oyarzun MA, Rauch MC, Salas MR, San Martin RE, Claude AA, Yanez AJ, Slebe JC, Carcamo JG: Effect of tacrolimus on activity and expression of P-glycoprotein and ATP-binding cassette transporter A5 (ABCA5) proteins in hematoencephalic barrier cells. Biol Pharm Bull. 2008 Oct;31(10):1911-6. [PubMed:18827354 ]