MiMeDB: Showing metabocard for Oscillatoxin I (MMDBc0028550)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 18:15:46 UTC

Update Date

2025-10-07 16:07:51 UTC

Metabolite ID

MMDBc0028550

Metabolite Identification

Common Name

Oscillatoxin I

Description

Oscillatoxin I is a member of the aplysiatoxin chemical class, characterized as a metabolite derived from a marine cyanobacterium. The chemical structure of this compound has been elucidated using advanced spectroscopic techniques, including high-resolution mass spectrometry (HR-MS) and both one-dimensional and two-dimensional nuclear magnetic resonance (NMR) spectroscopy (PMID:31234410 ). Oscillatoxin I exhibits notable cytotoxic properties, demonstrating significant activity against the L1210 mouse lymphoma cell line, indicating its potential impact on cellular pathways related to cancer (PMID:31234410 ). Additionally, it has been shown to inhibit the growth of the marine diatom Nitzschia amabilis, suggesting its involvement in ecological interactions and possibly influencing marine food webs (PMID:31234410 ). The structural and biological characteristics of Oscillatoxin I position it as a compound of interest in both chemical and biological research contexts.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152120152D          

 50 52  0  0  1  0            999 V2000
    1.1928    6.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    7.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    2.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766    7.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    3.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    4.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680    5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    5.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376    6.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081    8.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4782    7.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7628    6.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831    3.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4275    6.2427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8932    3.4363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5015    7.2312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3980    8.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    7.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8131    4.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9381    7.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878    6.5546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9734    6.5546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7787    7.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1633    4.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5430    3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081    6.2427    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    9.3609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4554    8.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734    4.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531    6.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    7.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    4.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5430    6.0868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    5.9309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    6.8664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    3.5923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1128    6.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    7.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    5.9600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    6.3986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  2  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 17  1  1  1  0  0  0
 17  8  1  0  0  0  0
 18  2  1  6  0  0  0
 18  9  1  0  0  0  0
 19  3  1  6  0  0  0
 19 16  1  0  0  0  0
 20  4  1  1  0  0  0
 21 10  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  2  0  0  0  0
 25 13  1  0  0  0  0
 25 22  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
 32  5  1  0  0  0  0
 32  6  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  1  0  0  0  0
 34 21  1  0  0  0  0
 35 27  2  0  0  0  0
 29 36  1  1  0  0  0
 37 30  2  0  0  0  0
 38 31  2  0  0  0  0
 39  7  1  0  0  0  0
 25 39  1  1  0  0  0
 40 20  1  0  0  0  0
 40 27  1  0  0  0  0
 26 41  1  1  0  0  0
 41 31  1  0  0  0  0
 42  8  1  0  0  0  0
 43 11  1  0  0  0  0
 17 44  1  6  0  0  0
 18 45  1  1  0  0  0
 19 46  1  1  0  0  0
 20 47  1  6  0  0  0
 25 48  1  1  0  0  0
 26 49  1  6  0  0  0
 29 50  1  1  0  0  0
M  END


  Mrv1652305152120152D          

 50 52  0  0  1  0            999 V2000
    1.1928    6.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    7.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    2.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766    7.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    3.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    4.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6680    5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    5.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376    6.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081    8.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    5.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4782    7.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7628    6.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831    3.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4275    6.2427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8932    3.4363    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5015    7.2312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3980    8.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    7.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8131    4.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9381    7.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878    6.5546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9734    6.5546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7787    7.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6232    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    5.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1633    4.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5430    3.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081    6.2427    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    9.3609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4554    8.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574    4.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734    4.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531    6.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9992    7.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628    4.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5430    6.0868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    5.9309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    6.8664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    3.5923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1128    6.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    7.3341    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5454    5.9600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3827    6.3986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  2  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 17  1  1  1  0  0  0
 17  8  1  0  0  0  0
 18  2  1  6  0  0  0
 18  9  1  0  0  0  0
 19  3  1  6  0  0  0
 19 16  1  0  0  0  0
 20  4  1  1  0  0  0
 21 10  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
 24 22  2  0  0  0  0
 25 13  1  0  0  0  0
 25 22  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
 27 15  1  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 19  1  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
 32  5  1  0  0  0  0
 32  6  1  0  0  0  0
 32 16  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  1  0  0  0  0
 34 21  1  0  0  0  0
 35 27  2  0  0  0  0
 29 36  1  1  0  0  0
 37 30  2  0  0  0  0
 38 31  2  0  0  0  0
 39  7  1  0  0  0  0
 25 39  1  1  0  0  0
 40 20  1  0  0  0  0
 40 27  1  0  0  0  0
 26 41  1  1  0  0  0
 41 31  1  0  0  0  0
 42  8  1  0  0  0  0
 43 11  1  0  0  0  0
 17 44  1  6  0  0  0
 18 45  1  1  0  0  0
 19 46  1  1  0  0  0
 20 47  1  6  0  0  0
 25 48  1  1  0  0  0
 26 49  1  6  0  0  0
 29 50  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0028550

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)CC[C@]([H])(OC)C1=C(Br)C=CC(O)=C1)C1=C(C(=O)O[C@]2([H])CC(=O)O[C@]2([H])C)C(=O)[C@]([H])(C)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H43BrO8/c1-17(29(36)18(2)9-13-25(39-7)22-14-21(34)10-12-24(22)33)8-11-23-28(30(37)19(3)16-32(23,5)6)31(38)41-26-15-27(35)40-20(26)4/h8,10-12,14,17-20,25-26,29,34,36H,9,13,15-16H2,1-7H3/b11-8+/t17-,18-,19+,20+,25-,26+,29-/m0/s1

> <INCHI_KEY>
QKLWRXPNVSGLOD-BZILHIHASA-N

> <FORMULA>
C32H43BrO8

> <MOLECULAR_WEIGHT>
635.592

> <EXACT_MASS>
634.214131

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
64.03290006997662

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-methyl-5-oxooxolan-3-yl (5R)-2-[(1E,3S,4R,5S,8S)-8-(2-bromo-5-hydroxyphenyl)-4-hydroxy-8-methoxy-3,5-dimethyloct-1-en-1-yl]-3,3,5-trimethyl-6-oxocyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
6.54077075233333

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.285021915390512

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.918099660752597

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7642064157374903

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
160.24010000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-methyl-5-oxooxolan-3-yl (5R)-2-[(1E,3S,4R,5S,8S)-8-(2-bromo-5-hydroxyphenyl)-4-hydroxy-8-methoxy-3,5-dimethyloct-1-en-1-yl]-3,3,5-trimethyl-6-oxocyclohex-1-ene-1-carboxylate

> <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       2.227  12.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.294  13.108   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.276   5.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.863  13.528   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.776   6.093   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.401   8.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.847  10.489   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.731   9.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.310  11.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.855  15.728   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.243   9.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.359  14.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.318  12.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  14.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.757  12.683   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.755   6.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.722  10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.798  11.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.267   6.415   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.403  13.498   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.343  16.019   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.839  13.399   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.251   8.743   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.351  13.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.831  12.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.284  12.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.787  14.222   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.763   9.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.210  10.489   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.771   7.870   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.267  10.489   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.747   7.288   0.000  0.00  0.00           C+0
HETATM   33 Br   UNK     0      -7.855  11.653   0.000  0.00  0.00          Br+0
HETATM   34  O   UNK     0      -5.839  17.474   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.050  15.103   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.294   9.034   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.284   8.161   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.259  11.653   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       9.332  14.726   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       8.780  10.780   0.000  0.00  0.00           O+0
HETATM   42  H   UNK     0       1.424   8.801   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.747  11.362   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.235  11.071   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.806  12.817   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.780   6.706   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       7.677  12.140   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.327  13.690   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      10.351  11.125   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.714  11.944   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   32                                                            
CONECT    6   32                                                            
CONECT    7   39                                                            
CONECT    8   11   17   42                                                  
CONECT    9   13   18                                                       
CONECT   10   12   21                                                       
CONECT   11    8   23   43                                                  
CONECT   12   10   24                                                       
CONECT   13    9   25                                                       
CONECT   14   21   22                                                       
CONECT   15   26   27                                                       
CONECT   16   19   32                                                       
CONECT   17    1    8   29   44                                             
CONECT   18    2    9   29   45                                             
CONECT   19    3   16   30   46                                             
CONECT   20    4   26   40   47                                             
CONECT   21   10   14   34                                                  
CONECT   22   14   24   25                                                  
CONECT   23   11   28   32                                                  
CONECT   24   12   22   33                                                  
CONECT   25   13   22   39   48                                             
CONECT   26   15   20   41   49                                             
CONECT   27   15   35   40                                                  
CONECT   28   23   30   31                                                  
CONECT   29   17   18   36   50                                             
CONECT   30   19   28   37                                                  
CONECT   31   28   38   41                                                  
CONECT   32    5    6   16   23                                             
CONECT   33   24                                                            
CONECT   34   21                                                            
CONECT   35   27                                                            
CONECT   36   29                                                            
CONECT   37   30                                                            
CONECT   38   31                                                            
CONECT   39    7   25                                                       
CONECT   40   20   27                                                       
CONECT   41   26   31                                                       
CONECT   42    8                                                            
CONECT   43   11                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   29                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

Synonyms

Not Available

Molecular Formula

C₃₂H₄₃BrO₈

Average Mass

635.592

Monoisotopic Mass

634.214131

IUPAC Name

(2R,3R)-2-methyl-5-oxooxolan-3-yl (5R)-2-[(1E,3S,4R,5S,8S)-8-(2-bromo-5-hydroxyphenyl)-4-hydroxy-8-methoxy-3,5-dimethyloct-1-en-1-yl]-3,3,5-trimethyl-6-oxocyclohex-1-ene-1-carboxylate

Traditional Name

(2R,3R)-2-methyl-5-oxooxolan-3-yl (5R)-2-[(1E,3S,4R,5S,8S)-8-(2-bromo-5-hydroxyphenyl)-4-hydroxy-8-methoxy-3,5-dimethyloct-1-en-1-yl]-3,3,5-trimethyl-6-oxocyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)CC[C@]([H])(OC)C1=C(Br)C=CC(O)=C1)C1=C(C(=O)O[C@]2([H])CC(=O)O[C@]2([H])C)C(=O)[C@]([H])(C)CC1(C)C

InChI Identifier

InChI=1S/C32H43BrO8/c1-17(29(36)18(2)9-13-25(39-7)22-14-21(34)10-12-24(22)33)8-11-23-28(30(37)19(3)16-32(23,5)6)31(38)41-26-15-27(35)40-20(26)4/h8,10-12,14,17-20,25-26,29,34,36H,9,13,15-16H2,1-7H3/b11-8+/t17-,18-,19+,20+,25-,26+,29-/m0/s1

InChI Key

QKLWRXPNVSGLOD-BZILHIHASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Cyclofarsesane sesquiterpenoid
Sesquiterpenoid
Benzylether
4-bromophenol
4-halophenol
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Halobenzene
Bromobenzene
Benzenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Aryl halide
Aryl bromide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	5.36	ALOGPS
logP	6.54	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	160.24 m³·mol⁻¹	ChemAxon
Polarizability	64.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

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	Cyanobacteria	1	Human feces	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

76826978

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684847

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 Oscillatoxin I (MMDBc0028550)

MOL for #<Metabolite:0x00007fadd75f4e48>

3D MOL for #<Metabolite:0x00007fadd75f4e48>

3D SDF for #<Metabolite:0x00007fadd75f4e48>

3D-SDF for #<Metabolite:0x00007fadd75f4e48>

PDB for #<Metabolite:0x00007fadd75f4e48>

3D PDB for #<Metabolite:0x00007fadd75f4e48>

SMILES for #<Metabolite:0x00007fadd75f4e48>

INCHI for #<Metabolite:0x00007fadd75f4e48>

Structure for #<Metabolite:0x00007fadd75f4e48>

3D Structure for #<Metabolite:0x00007fadd75f4e48>