MiMeDB: Showing metabocard for FR252921 (MMDBc0015755)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:31:49 UTC

Update Date

2025-10-07 16:06:27 UTC

Metabolite ID

MMDBc0015755

Metabolite Identification

Common Name

FR252921

Description

FR252921 is a macrocyclic polyene, specifically classified as a potent immunosuppressive agent. This compound has garnered attention for its unique mode of action and its potential applications in biomedical research. The synthesis of FR252921 has been explored through various methodologies, including a formal synthesis that emphasizes a ruthenium-catalyzed approach, which is noted for being step-economic and environmentally benign (PMID:35274951 ). Key features of its synthesis involve the preparation of a triene moiety followed by consecutive peptide couplings (PMID:35274951 ). Additionally, FR252921 is part of a family of related compounds, including FR252922 and FR256523, all recognized for their immunosuppressive properties (PMID:31436963 ). Enantioselective synthesis techniques have also been employed to construct specific segments of FR252921, highlighting the compound's complexity and the precision required in its synthesis (PMID:27818534 ). The development of concise and convergent synthetic routes has further facilitated the study of FR252921 and its analogues, underscoring its significance in the field of natural product chemistry (PMID:19219867 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108312D          

 48 48  0  0  1  0            999 V2000
    5.8464    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9911    6.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5095   12.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5608    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2753    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9898    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7043    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4187    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1332    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8953    7.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2678    8.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3040    7.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3812    9.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5621    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5579    6.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2230   10.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2766    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7379    6.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   10.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4163    8.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1284   11.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9911    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6003   11.8952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8064   11.6707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7056    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3935    9.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9329    7.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4240   11.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1884   11.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   10.5359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4543   12.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5764    9.8618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6224    6.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6044   12.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2300    7.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5601    7.4314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    8.4099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477    8.9762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7741    6.6668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2058    9.4961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5621    6.9137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7824    6.1988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2766    8.9762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6924    6.0782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6910   11.0752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1585   10.9246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4200    8.5637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  2  0  0  0  0
 24  3  1  1  0  0  0
 25 22  1  0  0  0  0
 25 24  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 30 20  1  4  0  0  0
 30 29  2  0  0  0  0
 31 22  1  4  0  0  0
 31 27  2  0  0  0  0
 25 32  1  1  0  0  0
 33 27  1  0  0  0  0
 34 28  2  0  0  0  0
 35 29  1  0  0  0  0
 36 26  1  0  0  0  0
 36 28  1  0  0  0  0
 37 10  1  0  0  0  0
 38 11  1  0  0  0  0
 39 12  1  0  0  0  0
 40 13  1  0  0  0  0
 41 14  1  0  0  0  0
 42 15  1  0  0  0  0
 43 16  1  0  0  0  0
 44 18  1  0  0  0  0
 45 19  1  0  0  0  0
 24 46  1  1  0  0  0
 25 47  1  1  0  0  0
 48 26  1  0  0  0  0
M  END


  Mrv1652305152108312D          

 48 48  0  0  1  0            999 V2000
    5.8464    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9911    6.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5095   12.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5608    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2753    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9898    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7043    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4187    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1332    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8953    7.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2678    8.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3040    7.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3812    9.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5621    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5579    6.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2230   10.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2766    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7379    6.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8105   10.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4163    8.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1284   11.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9911    7.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6003   11.8952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8064   11.6707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7056    8.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3935    9.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9329    7.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4240   11.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1884   11.5393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   10.5359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4543   12.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5764    9.8618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6224    6.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6044   12.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2300    7.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5601    7.4314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    8.4099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477    8.9762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7741    6.6668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2058    9.4961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5621    6.9137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7824    6.1988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2766    8.9762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6924    6.0782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6910   11.0752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1585   10.9246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4200    8.5637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  2  0  0  0  0
 24  3  1  1  0  0  0
 25 22  1  0  0  0  0
 25 24  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27 21  1  0  0  0  0
 28 19  1  0  0  0  0
 29 24  1  0  0  0  0
 30 20  1  4  0  0  0
 30 29  2  0  0  0  0
 31 22  1  4  0  0  0
 31 27  2  0  0  0  0
 25 32  1  1  0  0  0
 33 27  1  0  0  0  0
 34 28  2  0  0  0  0
 35 29  1  0  0  0  0
 36 26  1  0  0  0  0
 36 28  1  0  0  0  0
 37 10  1  0  0  0  0
 38 11  1  0  0  0  0
 39 12  1  0  0  0  0
 40 13  1  0  0  0  0
 41 14  1  0  0  0  0
 42 15  1  0  0  0  0
 43 16  1  0  0  0  0
 44 18  1  0  0  0  0
 45 19  1  0  0  0  0
 24 46  1  1  0  0  0
 25 47  1  1  0  0  0
 48 26  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015755

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCC)=C(\[H])/C(/[H])=C(\C)C1([H])CC(O)=NC[C@]([H])(O)[C@]([H])(C)C(O)=NCC\C([H])=C(\[H])/C(/[H])=C(/[H])\C(\[H])=C([H])/C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H44N2O5/c1-4-5-6-7-8-9-12-15-18-23(2)26-21-27(33)31-22-25(32)24(3)29(35)30-20-17-14-11-10-13-16-19-28(34)36-26/h10-16,18-19,24-26,32H,4-9,17,20-22H2,1-3H3,(H,30,35)(H,31,33)/b13-10-,14-11-,15-12+,19-16-,23-18+/t24-,25-,26?/m0/s1

> <INCHI_KEY>
BMWFPIGVZGRBAD-VRQYISITSA-N

> <FORMULA>
C29H44N2O5

> <MOLECULAR_WEIGHT>
500.68

> <EXACT_MASS>
500.325022525

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.59219559094397

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
5.004166690035005

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.048411091960033

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4391588873772396

> <JCHEM_PKA_STRONGEST_BASIC>
6.2011128294635025

> <JCHEM_POLAR_SURFACE_AREA>
111.71000000000001

> <JCHEM_REFRACTIVITY>
149.93880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.95e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      10.913  14.446   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.250  12.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.951  23.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.247  15.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.581  14.446   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.914  15.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.248  14.446   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.582  15.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.915  14.446   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.405  14.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.100  16.158   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.249  15.216   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.301  13.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.311  17.684   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.583  14.446   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.908  13.053   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.016  19.195   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.916  15.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.377  12.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.246  20.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.044  16.658   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.373  20.908   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.250  14.446   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.120  22.204   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.639  21.785   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.584  15.216   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.001  18.197   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.875  13.220   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.658  22.120   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      32.085  21.540   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      25.461  19.667   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0      26.981  23.178   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      23.476  18.409   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      27.295  11.794   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      30.995  23.622   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      26.563  14.027   0.000  0.00  0.00           O+0
HETATM   37  H   UNK     0      34.645  13.872   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      35.570  15.698   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      20.249  16.756   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      33.178  12.445   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      35.851  17.726   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      21.583  12.906   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      31.327  11.571   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      22.916  16.756   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      29.293  11.346   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      29.290  20.674   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      28.296  20.393   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      26.917  15.986   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   12                                                       
CONECT   10   11   13   37                                                  
CONECT   11   10   14   38                                                  
CONECT   12    9   15   39                                                  
CONECT   13   10   16   40                                                  
CONECT   14   11   17   41                                                  
CONECT   15   12   18   42                                                  
CONECT   16   13   19   43                                                  
CONECT   17   14   20                                                       
CONECT   18   15   23   44                                                  
CONECT   19   16   28   45                                                  
CONECT   20   17   30                                                       
CONECT   21   26   27                                                       
CONECT   22   25   31                                                       
CONECT   23    2   18   26                                                  
CONECT   24    3   25   29   46                                             
CONECT   25   22   24   32   47                                             
CONECT   26   21   23   36   48                                             
CONECT   27   21   31   33                                                  
CONECT   28   19   34   36                                                  
CONECT   29   24   30   35                                                  
CONECT   30   20   29                                                       
CONECT   31   22   27                                                       
CONECT   32   25                                                            
CONECT   33   27                                                            
CONECT   34   28                                                            
CONECT   35   29                                                            
CONECT   36   26   28                                                       
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   96    0
END

Synonyms

Not Available

Molecular Formula

C₂₉H₄₄N₂O₅

Average Mass

500.68

Monoisotopic Mass

500.325022525

IUPAC Name

(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

Traditional Name

(7R,8S,13Z,15Z,17Z)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-4,7,9-trihydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-4,9,13,15,17-pentaen-19-one

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCC)=C(\[H])/C(/[H])=C(\C)C1([H])CC(O)=NC[C@]([H])(O)[C@]([H])(C)C(O)=NCC\C([H])=C(\[H])/C(/[H])=C(/[H])\C(\[H])=C([H])/C(=O)O1

InChI Identifier

InChI=1S/C29H44N2O5/c1-4-5-6-7-8-9-12-15-18-23(2)26-21-27(33)31-22-25(32)24(3)29(35)30-20-17-14-11-10-13-16-19-28(34)36-26/h10-16,18-19,24-26,32H,4-9,17,20-22H2,1-3H3,(H,30,35)(H,31,33)/b13-10-,14-11-,15-12+,19-16-,23-18+/t24-,25-,26?/m0/s1

InChI Key

BMWFPIGVZGRBAD-VRQYISITSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0009 g/L	ALOGPS
logP	5.41	ALOGPS
logP	5	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.71 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	149.94 m³·mol⁻¹	ChemAxon
Polarizability	57.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587425

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for FR252921 (MMDBc0015755)

MOL for #<Metabolite:0x00007f8db6c69008>

3D MOL for #<Metabolite:0x00007f8db6c69008>

3D SDF for #<Metabolite:0x00007f8db6c69008>

3D-SDF for #<Metabolite:0x00007f8db6c69008>

PDB for #<Metabolite:0x00007f8db6c69008>

3D PDB for #<Metabolite:0x00007f8db6c69008>

SMILES for #<Metabolite:0x00007f8db6c69008>

INCHI for #<Metabolite:0x00007f8db6c69008>

Structure for #<Metabolite:0x00007f8db6c69008>

3D Structure for #<Metabolite:0x00007f8db6c69008>