Showing metabocard for Bafilomycin A1 (MMDBc0019344)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 09:26:10 UTC
Update Date2025-10-07 16:04:16 UTC
Metabolite IDMMDBc0019344
Metabolite Identification
Common NameBafilomycin A1
DescriptionBafilomycin A1 is a macrolide antibiotic belonging to the class of v-ATPase inhibitors. Its chemical structure features a complex polyene backbone with multiple hydroxyl and methoxy groups, contributing to its biological activity. Bafilomycin A1 primarily functions by inhibiting the vacuolar ATPase (v-ATPase), which is crucial for acidifying intracellular compartments, including lysosomes. This inhibition disrupts autophagic processes, as evidenced by studies showing that Bafilomycin A1 enhances the pro-apoptotic activity of chemotherapeutic agents like CPX by blocking autophagy in K562 cells (PMID:41049452 ). Additionally, it has been shown to reverse cisplatin resistance by affecting autophagy-related markers (PMID:41049434 ). The compound also influences exocytotic mechanisms in a calcium-dependent manner (PMID:41015092 ) and prevents degradation of c-MYC when combined with other agents (PMID:41014667 ). Its role in late-stage autophagy inhibition is further supported by the accumulation of specific autophagy markers (PMID:40964235 ). Furthermore, Bafilomycin A1 has implications in lysosomal degradation pathways, as indicated by its inhibitory effects on Tau degradation (PMID:40963907 ) and its role in restricting viral replication (PMID:40920489 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00005560b132f0e8>


  Mrv1652305152111262D          

 49 50  0  0  0  0            999 V2000
    2.8962    3.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8204    7.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099    5.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1703    7.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7796    5.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    3.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1236    8.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8574    9.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6677    8.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0877    8.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0325    8.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8962    4.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 49 17  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005560b132f0e8>

Download
3D SDF for #<Metabolite:0x00005560b132f0e8>

  Mrv1652305152111262D          

 49 50  0  0  0  0            999 V2000
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    3.6107    4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8204    7.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1703    7.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4673    3.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2192    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6885    5.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0838    5.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    4.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4058    7.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370    6.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8456    4.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7901    3.8951    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
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 49 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019344

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C1=C(\[H])/C(/[H])=C(C)/CC(C)C(O)C(C)\C([H])=C(/C)\C(\[H])=C(OC)\C(=O)OC(C(C)C(O)C(C)C2(O)CC(O)C(C)C(O2)C(C)C)C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-

> <INCHI_KEY>
XDHNQDDQEHDUTM-YJSQNSDISA-N

> <FORMULA>
C35H58O9

> <MOLECULAR_WEIGHT>
622.84

> <EXACT_MASS>
622.408083448

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
69.07206105464255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,5E,11E,13E)-16-{4-[2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl}-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
5.081522923

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.36775477175016

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.6894535546142

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7344085907907704

> <JCHEM_POLAR_SURFACE_AREA>
134.91

> <JCHEM_REFRACTIVITY>
174.52820000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5E,11E,13E)-16-[4-(2,4-dihydroxy-6-isopropyl-5-methyloxan-2-yl)-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00005560b132f0e8>
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PDB for #<Metabolite:0x00005560b132f0e8>
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       5.406   6.915   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.740   9.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.131  14.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.552  10.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.518  13.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.789   9.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.739   6.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.231  15.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.276  14.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.601  17.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.480  12.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.437  15.941   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.846  16.561   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.897  15.908   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.394  14.938   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.425   9.441   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.476   8.788   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.405  10.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.406   8.455   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.959  15.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.885   9.408   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.014  13.529   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.490  10.554   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.739   8.455   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.757  13.627   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.749  12.715   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.405   9.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.832  14.795   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.363   9.852   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.048  11.989   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.232  12.448   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.073   9.225   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.274  13.360   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.928  10.411   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.739  11.535   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.072   8.455   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -11.565  11.722   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.294  11.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.863   9.298   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       3.729  12.715   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.533  15.623   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.191  11.151   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.308  11.820   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       4.073  10.765   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      -5.770  14.438   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -7.114  18.078   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.277  17.317   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -9.045   8.032   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.208   7.271   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   23                                                            
CONECT    7   24                                                            
CONECT    8   25                                                            
CONECT    9   26                                                            
CONECT   10   41                                                            
CONECT   11   42                                                            
CONECT   12   13   14   45                                                  
CONECT   13   12   20   46                                                  
CONECT   14   12   28   47                                                  
CONECT   15   20   22                                                       
CONECT   16   21   23   48                                                  
CONECT   17   21   29   49                                                  
CONECT   18   27   35                                                       
CONECT   19    1    2   32                                                  
CONECT   20    3   13   15                                                  
CONECT   21    4   16   17                                                  
CONECT   22    5   15   30                                                  
CONECT   23    6   16   30                                                  
CONECT   24    7   27   32                                                  
CONECT   25    8   31   33                                                  
CONECT   26    9   31   35                                                  
CONECT   27   18   24   36                                                  
CONECT   28   14   33   41                                                  
CONECT   29   17   34   42                                                  
CONECT   30   22   23   37                                                  
CONECT   31   25   26   38                                                  
CONECT   32   19   24   44                                                  
CONECT   33   25   28   43                                                  
CONECT   34   29   39   43                                                  
CONECT   35   18   26   40   44                                             
CONECT   36   27                                                            
CONECT   37   30                                                            
CONECT   38   31                                                            
CONECT   39   34                                                            
CONECT   40   35                                                            
CONECT   41   10   28                                                       
CONECT   42   11   29                                                       
CONECT   43   33   34                                                       
CONECT   44   32   35                                                       
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  100    0
END

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3D PDB for #<Metabolite:0x00005560b132f0e8>
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SMILES for #<Metabolite:0x00005560b132f0e8>
[H]\C1=C(\[H])/C(/[H])=C(C)/CC(C)C(O)C(C)\C([H])=C(/C)\C(\[H])=C(OC)\C(=O)OC(C(C)C(O)C(C)C2(O)CC(O)C(C)C(O2)C(C)C)C1OC
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INCHI for #<Metabolite:0x00005560b132f0e8>
InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-
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SynonymsNot Available
Molecular FormulaC35H58O9
Average Mass622.84
Monoisotopic Mass622.408083448
IUPAC Name(3Z,5E,11E,13E)-16-{4-[2,4-dihydroxy-5-methyl-6-(propan-2-yl)oxan-2-yl]-3-hydroxypentan-2-yl}-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
Traditional Name(3Z,5E,11E,13E)-16-[4-(2,4-dihydroxy-6-isopropyl-5-methyloxan-2-yl)-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
CAS Registry NumberNot Available
SMILES
[H]\C1=C(\[H])/C(/[H])=C(C)/CC(C)C(O)C(C)\C([H])=C(/C)\C(\[H])=C(OC)\C(=O)OC(C(C)C(O)C(C)C2(O)CC(O)C(C)C(O2)C(C)C)C1OC
InChI Identifier
InChI=1S/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-
InChI KeyXDHNQDDQEHDUTM-YJSQNSDISA-N