MiMeDB: Showing metabocard for Bafilomycin C1 (MMDBc0015244)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:07:05 UTC

Update Date

2025-10-07 16:06:23 UTC

Metabolite ID

MMDBc0015244

Metabolite Identification

Common Name

Bafilomycin C1

Description

Bafilomycin C1 is a macrolide antibiotic metabolite isolated from the bacterium Streptomyces albolongus, known for its potent antibacterial and cytotoxic properties. This compound has been shown to induce G0/G1 cell-cycle arrest and trigger mitochondrial-mediated apoptosis in human hepatocellular cancer SMMC7721 cells, highlighting its potential as an anticancer agent (PMID:29752478 ). Bafilomycin C1 exhibits strong cytotoxicity against various cancer cell lines, as evidenced by MTT assays that demonstrate its ability to retard cell growth and proliferation (PMID:29752478 ). Mechanistically, it downregulates key cell-cycle regulators such as cyclin D3, cyclin E1, CDK2, CDK4, and CDK6, while upregulating p21, leading to cell-cycle disruption (PMID:29752478 ). Additionally, bafilomycin C1 induces oxidative stress, causing mitochondrial membrane dysfunction and altering the expression of apoptotic markers, including decreasing Bcl-2 and increasing Bax, p53, and cleaved caspases (PMID:29752478 ). In vivo studies further support its efficacy, showing suppression of tumor growth in mouse models with minimal side effects (PMID:29752478 ). These findings suggest that bafilomycin C1 could be a promising candidate for therapeutic applications in hepatic cellular cancer.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108072D          

 58 59  0  0  0  0            999 V2000
    4.8923    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441    7.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    6.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    7.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034    5.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    8.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    6.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    9.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    6.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    8.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915    9.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    8.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    8.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371    5.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571    4.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    5.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778    3.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874    8.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3123    5.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    7.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076    5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    3.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186    6.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590    8.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388    5.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0066    6.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    6.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580    7.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077    5.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    5.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    3.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235    1.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191    6.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    7.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    5.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    6.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548    8.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    6.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    3.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400    6.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    5.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7149    8.0210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347    9.9711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207    9.5635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    3.8976    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055    1.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    4.5892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139    4.1816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 16 15  2  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22 13  2  0  0  0  0
 22 17  1  0  0  0  0
 23  4  1  0  0  0  0
 23 18  2  0  0  0  0
 23 19  1  0  0  0  0
 24  5  1  0  0  0  0
 24 17  1  0  0  0  0
 25  6  1  0  0  0  0
 25 18  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 14  1  0  0  0  0
 30 19  2  0  0  0  0
 31 20  1  0  0  0  0
 31 26  1  0  0  0  0
 32 15  1  0  0  0  0
 33 16  1  0  0  0  0
 34 24  1  0  0  0  0
 34 25  1  0  0  0  0
 35 27  1  0  0  0  0
 35 28  1  0  0  0  0
 36 21  1  0  0  0  0
 36 26  1  0  0  0  0
 37 27  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
 39 20  1  0  0  0  0
 39 28  1  0  0  0  0
 40 32  2  0  0  0  0
 41 32  1  0  0  0  0
 42 33  2  0  0  0  0
 43 34  1  0  0  0  0
 44 35  1  0  0  0  0
 45 38  2  0  0  0  0
 46 39  1  0  0  0  0
 47 10  1  0  0  0  0
 47 29  1  0  0  0  0
 48 11  1  0  0  0  0
 48 30  1  0  0  0  0
 49 31  1  0  0  0  0
 49 33  1  0  0  0  0
 50 37  1  0  0  0  0
 50 38  1  0  0  0  0
 51 36  1  0  0  0  0
 51 39  1  0  0  0  0
 52 12  1  0  0  0  0
 53 13  1  0  0  0  0
 54 14  1  0  0  0  0
 55 15  1  0  0  0  0
 56 16  1  0  0  0  0
 57 18  1  0  0  0  0
 58 19  1  0  0  0  0
M  END


  Mrv1652305152108072D          

 58 59  0  0  0  0            999 V2000
    4.8923    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441    7.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    6.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    7.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034    5.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    8.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    6.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    9.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235    6.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    8.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915    9.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2885    8.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    8.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371    5.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571    4.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    5.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778    3.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874    8.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3123    5.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886    7.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7076    5.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    3.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    7.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186    6.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590    8.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388    5.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235    2.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    3.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0066    6.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007    6.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580    7.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077    5.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    5.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    3.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235    1.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    2.6601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191    6.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    7.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    5.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    6.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548    8.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4045    6.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    3.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400    6.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4633    5.1351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7149    8.0210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4347    9.9711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207    9.5635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    3.8976    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055    1.8351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    4.5892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139    4.1816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 16 15  2  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22 13  2  0  0  0  0
 22 17  1  0  0  0  0
 23  4  1  0  0  0  0
 23 18  2  0  0  0  0
 23 19  1  0  0  0  0
 24  5  1  0  0  0  0
 24 17  1  0  0  0  0
 25  6  1  0  0  0  0
 25 18  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 29 14  1  0  0  0  0
 30 19  2  0  0  0  0
 31 20  1  0  0  0  0
 31 26  1  0  0  0  0
 32 15  1  0  0  0  0
 33 16  1  0  0  0  0
 34 24  1  0  0  0  0
 34 25  1  0  0  0  0
 35 27  1  0  0  0  0
 35 28  1  0  0  0  0
 36 21  1  0  0  0  0
 36 26  1  0  0  0  0
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 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
 39 20  1  0  0  0  0
 39 28  1  0  0  0  0
 40 32  2  0  0  0  0
 41 32  1  0  0  0  0
 42 33  2  0  0  0  0
 43 34  1  0  0  0  0
 44 35  1  0  0  0  0
 45 38  2  0  0  0  0
 46 39  1  0  0  0  0
 47 10  1  0  0  0  0
 47 29  1  0  0  0  0
 48 11  1  0  0  0  0
 48 30  1  0  0  0  0
 49 31  1  0  0  0  0
 49 33  1  0  0  0  0
 50 37  1  0  0  0  0
 50 38  1  0  0  0  0
 51 36  1  0  0  0  0
 51 39  1  0  0  0  0
 52 12  1  0  0  0  0
 53 13  1  0  0  0  0
 54 14  1  0  0  0  0
 55 15  1  0  0  0  0
 56 16  1  0  0  0  0
 57 18  1  0  0  0  0
 58 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015244

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C(=O)OC1CC(O)(OC(C(C)C)C1C)C(C)C(O)C(C)C1OC(=O)\C(OC)=C(/[H])\C(\C)=C([H])\C(C)C(O)C(C)C\C(C)=C(/[H])\C(\[H])=C([H])\C1OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H60O12/c1-21(2)36-26(7)31(49-33(42)16-15-32(40)41)20-39(46,51-36)28(9)35(44)27(8)37-29(47-10)14-12-13-22(3)17-24(5)34(43)25(6)18-23(4)19-30(48-11)38(45)50-37/h12-16,18-19,21,24-29,31,34-37,43-44,46H,17,20H2,1-11H3,(H,40,41)/b14-12+,16-15+,22-13+,23-18+,30-19-

> <INCHI_KEY>
WUDBXVQNMOTFEE-FUGNQFJWSA-N

> <FORMULA>
C39H60O12

> <MOLECULAR_WEIGHT>
720.897

> <EXACT_MASS>
720.408477372

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
78.38653355697626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-5-methyl-6-(propan-2-yl)oxan-4-yl)oxy]-4-oxobut-2-enoic acid

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
5.938413049666665

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.688235748712135

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2176084544747052

> <JCHEM_PKA_STRONGEST_BASIC>
-0.734456827389011

> <JCHEM_POLAR_SURFACE_AREA>
178.27999999999994

> <JCHEM_REFRACTIVITY>
195.6430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-6-isopropyl-5-methyloxan-4-yl)oxy]-4-oxobut-2-enoic acid

> <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       9.132   8.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.799   5.736   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.696  14.732   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.116  11.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.082  14.397   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.353  10.261   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.131   5.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.205  15.609   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.625  11.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.835  17.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.044  13.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.001  16.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.411  17.096   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.538  16.442   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.203   5.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.130   4.966   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.958  15.473   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.989   9.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.040   9.322   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.798   9.586   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.799   7.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.523  16.031   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.450   9.943   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.579  14.064   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.054  11.089   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.131   7.276   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.678  14.162   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.141  11.535   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.603  15.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.072  10.387   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.798   8.046   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.537   4.966   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.464   5.736   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.612  12.524   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.668  12.982   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.465   8.046   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.162  13.895   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.508  10.945   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.131  10.356   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.871   5.736   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.537   3.426   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       3.798   4.966   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -7.129  12.256   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       6.185  13.250   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.573   9.833   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       6.121  11.535   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.902  16.157   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -0.755  11.686   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       2.464   7.276   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.128  12.355   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       6.465   9.586   0.000  0.00  0.00           O+0
HETATM   52  H   UNK     0      -1.334  14.972   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.678  18.613   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.159  17.852   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.203   7.276   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.130   3.426   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.609   8.567   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.773   7.806   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   24                                                            
CONECT    6   25                                                            
CONECT    7   26                                                            
CONECT    8   27                                                            
CONECT    9   28                                                            
CONECT   10   47                                                            
CONECT   11   48                                                            
CONECT   12   13   14   52                                                  
CONECT   13   12   22   53                                                  
CONECT   14   12   29   54                                                  
CONECT   15   16   32   55                                                  
CONECT   16   15   33   56                                                  
CONECT   17   22   24                                                       
CONECT   18   23   25   57                                                  
CONECT   19   23   30   58                                                  
CONECT   20   31   39                                                       
CONECT   21    1    2   36                                                  
CONECT   22    3   13   17                                                  
CONECT   23    4   18   19                                                  
CONECT   24    5   17   34                                                  
CONECT   25    6   18   34                                                  
CONECT   26    7   31   36                                                  
CONECT   27    8   35   37                                                  
CONECT   28    9   35   39                                                  
CONECT   29   14   37   47                                                  
CONECT   30   19   38   48                                                  
CONECT   31   20   26   49                                                  
CONECT   32   15   40   41                                                  
CONECT   33   16   42   49                                                  
CONECT   34   24   25   43                                                  
CONECT   35   27   28   44                                                  
CONECT   36   21   26   51                                                  
CONECT   37   27   29   50                                                  
CONECT   38   30   45   50                                                  
CONECT   39   20   28   46   51                                             
CONECT   40   32                                                            
CONECT   41   32                                                            
CONECT   42   33                                                            
CONECT   43   34                                                            
CONECT   44   35                                                            
CONECT   45   38                                                            
CONECT   46   39                                                            
CONECT   47   10   29                                                       
CONECT   48   11   30                                                       
CONECT   49   31   33                                                       
CONECT   50   37   38                                                       
CONECT   51   36   39                                                       
CONECT   52   12                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  118    0
END

Synonyms

Value	Source
Bafilomycin-C1	MeSH

Molecular Formula

C₃₉H₆₀O₁₂

Average Mass

720.897

Monoisotopic Mass

720.408477372

IUPAC Name

(2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-5-methyl-6-(propan-2-yl)oxan-4-yl)oxy]-4-oxobut-2-enoic acid

Traditional Name

(2E)-4-[(2-hydroxy-2-{3-hydroxy-4-[(4E,6E,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl}-6-isopropyl-5-methyloxan-4-yl)oxy]-4-oxobut-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C(=O)OC1CC(O)(OC(C(C)C)C1C)C(C)C(O)C(C)C1OC(=O)\C(OC)=C(/[H])\C(\C)=C([H])\C(C)C(O)C(C)C\C(C)=C(/[H])\C(\[H])=C([H])\C1OC)C(O)=O

InChI Identifier

InChI=1S/C39H60O12/c1-21(2)36-26(7)31(49-33(42)16-15-32(40)41)20-39(46,51-36)28(9)35(44)27(8)37-29(47-10)14-12-13-22(3)17-24(5)34(43)25(6)18-23(4)19-30(48-11)38(45)50-37/h12-16,18-19,21,24-29,31,34-37,43-44,46H,17,20H2,1-11H3,(H,40,41)/b14-12+,16-15+,22-13+,23-18+,30-19-

InChI Key

WUDBXVQNMOTFEE-FUGNQFJWSA-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
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	0.0072 g/L	ALOGPS
logP	4.21	ALOGPS
logP	5.94	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	-0.73	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	195.64 m³·mol⁻¹	ChemAxon
Polarizability	78.39 Å³	ChemAxon
Number of Rings	2	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

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	20.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	63.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	905.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	772.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	860.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	174.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	4463.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	98.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	416.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	685.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	154.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	136.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	221.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	9.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	94.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	117.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	514.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2065.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1597.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Bafilomycin C1_TMS_1	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	641.273
Gas Chromatography	Bafilomycin C1_TMS_2	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	820.952
Gas Chromatography	Bafilomycin C1_TMS_3	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	1852.19
Gas Chromatography	Bafilomycin C1_TMS_4	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	3300.98
Gas Chromatography	Bafilomycin C1_TMS_5	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	1740.26
Gas Chromatography	Bafilomycin C1_TMS_6	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	2182.04
Gas Chromatography	Bafilomycin C1_TMS_7	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	1963.85
Gas Chromatography	Bafilomycin C1_TMS_8	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	1133.23
Gas Chromatography	Bafilomycin C1_TMS_9	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	2573.51
Gas Chromatography	Bafilomycin C1_TMS_10	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard non polar	2025-10-23	1022.32
Gas Chromatography	Bafilomycin C1_TMS_1	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	1362.47
Gas Chromatography	Bafilomycin C1_TMS_2	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2745.45
Gas Chromatography	Bafilomycin C1_TMS_3	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	3482.01
Gas Chromatography	Bafilomycin C1_TMS_4	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2243.33
Gas Chromatography	Bafilomycin C1_TMS_5	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2148.04
Gas Chromatography	Bafilomycin C1_TMS_6	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	1796.3
Gas Chromatography	Bafilomycin C1_TMS_7	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O[Si](C)(C)C)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2789.37
Gas Chromatography	Bafilomycin C1_TMS_8	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2119.81
Gas Chromatography	Bafilomycin C1_TMS_9	CO/C1=C\C(C)=C\C(C)C(O)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O[Si](C)(C)C)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	3728.84
Gas Chromatography	Bafilomycin C1_TMS_10	CO/C1=C\C(C)=C\C(C)C(O[Si](C)(C)C)C(C)C/C(C)=C/C=C/C(OC)C(C(C)C(O)C(C)C2(O)CC(OC(=O)/C=C/C(=O)O[Si](C)(C)C)C(C)C(C(C)C)O2)OC1=O	standard polar	2025-10-23	2318.55

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	Actinobacteria	1		Metabolic reconstruction
Bacteria	Actinobacteria	1		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

C00014996

Chemspider ID

8525385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10349930

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 Bafilomycin C1 (MMDBc0015244)

MOL for #<Metabolite:0x00007f2e26886d18>

3D MOL for #<Metabolite:0x00007f2e26886d18>

3D SDF for #<Metabolite:0x00007f2e26886d18>

3D-SDF for #<Metabolite:0x00007f2e26886d18>

PDB for #<Metabolite:0x00007f2e26886d18>

3D PDB for #<Metabolite:0x00007f2e26886d18>

SMILES for #<Metabolite:0x00007f2e26886d18>

INCHI for #<Metabolite:0x00007f2e26886d18>

Structure for #<Metabolite:0x00007f2e26886d18>

3D Structure for #<Metabolite:0x00007f2e26886d18>