MiMeDB: Showing metabocard for Rhizoxin S2 (MMDBc0005835)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:16:58 UTC

Update Date

2025-10-07 16:05:04 UTC

Metabolite ID

MMDBc0005835

Metabolite Identification

Common Name

Rhizoxin S2

Description

Rhizoxin S2 is a member of the chemical class of antimitotic agents, specifically a metabolite produced by certain bacteria. It exhibits significant biological activity, demonstrating amoebicidal effects and lethality toward the model nematode Caenorhabditis elegans (PMID:36005392 ). In addition to its toxic effects on nematodes, Rhizoxin S2 induces notable changes in cell morphology and inhibits the growth of various organisms, including C. elegans, with its strongest growth inhibition being influenced by the spatial structure of the environment, such as agar versus liquid culture (PMID:34347373 ). Interestingly, while Rhizoxin S2 affects the growth of certain cells, it does not impact algal motility, which is more potently inhibited by orfamide A (IC50 = 4.1 μM) (PMID:34347373 ). Furthermore, research has explored the structural modifications of Rhizoxin S2, particularly the oxazole side chain, through mutasynthesis using engineered mutants to enhance its antitumor properties (PMID:23106078 ). This highlights the potential of Rhizoxin S2 in both ecological and therapeutic contexts.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101162D          

 61 63  0  0  1  0            999 V2000
    5.1435   -5.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482    4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0278   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1670   -1.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230   -7.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276    0.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9700   -2.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4654   -4.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954    0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841   -4.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263   -3.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954    1.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    0.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470    3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636    2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -5.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6964    3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9657    2.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -6.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1092    3.3710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4075   -2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -1.5857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9288   -7.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    2.4719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5810   -6.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1092   -0.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636    0.1225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4479    1.7097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9117    3.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6964   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685   -2.1296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4479    0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -6.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0951    4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776   -0.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1718    4.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5977    4.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1547   -1.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3497   -1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -7.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342   -0.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334    1.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856   -4.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4046    0.7238    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639   -3.7344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -2.6600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9657   -0.3358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886    3.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776    2.9303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -4.8087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    2.5619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3279   -1.0417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5938    2.0136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7732    2.5619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    0.0326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4496    0.5809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570    1.5488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7873   -2.3948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  2  0  0  0  0
 15 14  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  2  1  6  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 11  2  0  0  0  0
 24  4  1  1  0  0  0
 25  5  1  0  0  0  0
 26 12  1  0  0  0  0
 26 17  1  0  0  0  0
 26 18  1  1  0  0  0
 27 16  1  0  0  0  0
 27 20  2  0  0  0  0
 28 17  1  0  0  0  0
 28 22  1  0  0  0  0
 29 19  1  0  0  0  0
 29 24  1  0  0  0  0
 30 19  1  0  0  0  0
 31 15  1  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 34 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35  6  1  0  0  0  0
 35 30  1  0  0  0  0
 35 31  1  0  0  0  0
 36 25  2  0  0  0  0
 36 27  1  0  0  0  0
 37 28  1  0  0  0  0
 30 38  1  1  0  0  0
 39 32  2  0  0  0  0
 40 32  1  0  0  0  0
 41 33  2  0  0  0  0
 42  7  1  0  0  0  0
 34 42  1  6  0  0  0
 43 20  1  0  0  0  0
 43 25  1  0  0  0  0
 44 29  1  0  0  0  0
 44 33  1  0  0  0  0
 45 31  1  0  0  0  0
 45 35  1  0  0  0  0
 46  8  1  0  0  0  0
 47  9  1  0  0  0  0
 48 10  1  0  0  0  0
 49 11  1  0  0  0  0
 50 13  1  0  0  0  0
 51 14  1  0  0  0  0
 52 15  1  0  0  0  0
 53 16  1  0  0  0  0
 22 54  1  6  0  0  0
 24 55  1  6  0  0  0
 26 56  1  1  0  0  0
 57 28  1  0  0  0  0
 58 29  1  0  0  0  0
 30 59  1  1  0  0  0
 31 60  1  1  0  0  0
 34 61  1  6  0  0  0
M  END


  Mrv1652305152101162D          

 61 63  0  0  1  0            999 V2000
    5.1435   -5.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482    4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0278   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1670   -1.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230   -7.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276    0.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9700   -2.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4654   -4.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954    0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841   -4.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263   -3.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5954    1.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    0.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470    3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636    2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420   -5.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6964    3.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9657    2.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3470   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -6.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1092    3.3710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4075   -2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -1.5857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9288   -7.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797    2.4719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5810   -6.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1092   -0.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636    0.1225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4479    1.7097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9117    3.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6964   -0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685   -2.1296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4479    0.8847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8318   -6.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0951    4.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776   -0.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1718    4.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5977    4.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1547   -1.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3497   -1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379   -7.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342   -0.7765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334    1.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856   -4.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4046    0.7238    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639   -3.7344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0060   -2.6600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9657   -0.3358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886    3.7413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0776    2.9303    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -4.8087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    2.5619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3279   -1.0417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5938    2.0136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7732    2.5619    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    0.0326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4496    0.5809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2570    1.5488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7873   -2.3948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  2  0  0  0  0
 15 14  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  2  0  0  0  0
 22  2  1  6  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 11  2  0  0  0  0
 24  4  1  1  0  0  0
 25  5  1  0  0  0  0
 26 12  1  0  0  0  0
 26 17  1  0  0  0  0
 26 18  1  1  0  0  0
 27 16  1  0  0  0  0
 27 20  2  0  0  0  0
 28 17  1  0  0  0  0
 28 22  1  0  0  0  0
 29 19  1  0  0  0  0
 29 24  1  0  0  0  0
 30 19  1  0  0  0  0
 31 15  1  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 34 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35  6  1  0  0  0  0
 35 30  1  0  0  0  0
 35 31  1  0  0  0  0
 36 25  2  0  0  0  0
 36 27  1  0  0  0  0
 37 28  1  0  0  0  0
 30 38  1  1  0  0  0
 39 32  2  0  0  0  0
 40 32  1  0  0  0  0
 41 33  2  0  0  0  0
 42  7  1  0  0  0  0
 34 42  1  6  0  0  0
 43 20  1  0  0  0  0
 43 25  1  0  0  0  0
 44 29  1  0  0  0  0
 44 33  1  0  0  0  0
 45 31  1  0  0  0  0
 45 35  1  0  0  0  0
 46  8  1  0  0  0  0
 47  9  1  0  0  0  0
 48 10  1  0  0  0  0
 49 11  1  0  0  0  0
 50 13  1  0  0  0  0
 51 14  1  0  0  0  0
 52 15  1  0  0  0  0
 53 16  1  0  0  0  0
 22 54  1  6  0  0  0
 24 55  1  6  0  0  0
 26 56  1  1  0  0  0
 57 28  1  0  0  0  0
 58 29  1  0  0  0  0
 30 59  1  1  0  0  0
 31 60  1  1  0  0  0
 34 61  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005835

> <DATABASE_NAME>
MIME

> <SMILES>
[H]/C(=C(/[H])\C(\C)=C(/[H])C1=COC(C)=N1)/C(/[H])=C(\C)[C@]([H])(OC)[C@@]([H])(C)C1([H])C[C@]([H])(O)C2(C)O[C@]2([H])\C([H])=C([H])/[C@@]([H])(C)C([H])(O)C[C@]([H])(CC(O)=O)C\C([H])=C([H])/C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C35H49NO9/c1-21(16-27-20-43-25(5)36-27)10-8-11-23(3)34(42-7)24(4)29-19-30(38)35(6)31(45-35)15-14-22(2)28(37)17-26(18-32(39)40)12-9-13-33(41)44-29/h8-11,13-16,20,22,24,26,28-31,34,37-38H,12,17-19H2,1-7H3,(H,39,40)/b10-8+,13-9-,15-14-,21-16+,23-11+/t22-,24+,26-,28?,29?,30+,31-,34+,35?/m1/s1

> <INCHI_KEY>
FAIGGHHPKTYDHM-VRAWKDPKSA-N

> <FORMULA>
C35H49NO9

> <MOLECULAR_WEIGHT>
627.775

> <EXACT_MASS>
627.340732162

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
68.41490385474512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,7Z,10R,13R,14Z,16R)-2,12-dihydroxy-4-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-1,13-dimethyl-6-oxo-5,17-dioxabicyclo[14.1.0]heptadeca-7,14-dien-10-yl]acetic acid

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.073511870333332

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.824305388453801

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.166171295612571

> <JCHEM_PKA_STRONGEST_BASIC>
0.5948665808727922

> <JCHEM_POLAR_SURFACE_AREA>
151.85

> <JCHEM_REFRACTIVITY>
173.90920000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,7Z,10R,13R,14Z,16R)-2,12-dihydroxy-4-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-1,13-dimethyl-6-oxo-5,17-dioxabicyclo[14.1.0]heptadeca-7,14-dien-10-yl]acetic 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       9.601 -10.512   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.103   7.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.119  -6.501   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.645  -3.455   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.336 -14.721   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.145   0.636   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.877  -4.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.202  -7.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.045   1.652   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.744  -7.986   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.502  -5.981   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.045   3.192   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.455   0.229   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.981   5.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.892   4.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.985  -9.992   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.367   5.703   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.736   5.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.981  -0.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.730 -12.633   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.443  -9.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.404   6.293   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.961  -5.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.103  -2.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.467 -13.676   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.455   4.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.685 -11.502   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.944   6.293   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.404  -1.450   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.892   0.229   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.303   3.192   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.635   7.007   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.367  -0.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.261  -3.975   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.303   1.652   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       5.286 -12.147   0.000  0.00  0.00           N+0
HETATM   37  O   UNK     0      13.244   7.803   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       7.612  -0.627   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      15.254   7.688   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      17.916   7.862   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      15.222  -2.141   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      13.719  -3.480   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       6.977 -13.977   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      12.944  -1.450   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       6.969   2.422   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0      11.360  -8.507   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      17.555   1.351   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.586  -6.971   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       9.345  -4.965   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      16.736  -0.627   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       9.125   6.984   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.612   5.470   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.827  -8.976   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      11.704   4.782   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       9.945  -1.945   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      14.175   3.759   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      12.643   4.782   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      11.704   0.061   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      10.173   1.084   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       9.813   2.891   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      10.803  -4.470   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6   35                                                            
CONECT    7   42                                                            
CONECT    8   10   11   46                                                  
CONECT    9   12   13   47                                                  
CONECT   10    8   21   48                                                  
CONECT   11    8   23   49                                                  
CONECT   12    9   26                                                       
CONECT   13    9   33   50                                                  
CONECT   14   15   22   51                                                  
CONECT   15   14   31   52                                                  
CONECT   16   21   27   53                                                  
CONECT   17   26   28                                                       
CONECT   18   26   32                                                       
CONECT   19   29   30                                                       
CONECT   20   27   43                                                       
CONECT   21    1   10   16                                                  
CONECT   22    2   14   28   54                                             
CONECT   23    3   11   34                                                  
CONECT   24    4   29   34   55                                             
CONECT   25    5   36   43                                                  
CONECT   26   12   17   18   56                                             
CONECT   27   16   20   36                                                  
CONECT   28   17   22   37   57                                             
CONECT   29   19   24   44   58                                             
CONECT   30   19   35   38   59                                             
CONECT   31   15   35   45   60                                             
CONECT   32   18   39   40                                                  
CONECT   33   13   41   44                                                  
CONECT   34   23   24   42   61                                             
CONECT   35    6   30   31   45                                             
CONECT   36   25   27                                                       
CONECT   37   28                                                            
CONECT   38   30                                                            
CONECT   39   32                                                            
CONECT   40   32                                                            
CONECT   41   33                                                            
CONECT   42    7   34                                                       
CONECT   43   20   25                                                       
CONECT   44   29   33                                                       
CONECT   45   31   35                                                       
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   26                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   30                                                            
CONECT   60   31                                                            
CONECT   61   34                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

Synonyms

Not Available

Molecular Formula

C₃₅H₄₉NO₉

Average Mass

627.775

Monoisotopic Mass

627.340732162

IUPAC Name

2-[(2S,7Z,10R,13R,14Z,16R)-2,12-dihydroxy-4-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-1,13-dimethyl-6-oxo-5,17-dioxabicyclo[14.1.0]heptadeca-7,14-dien-10-yl]acetic acid

Traditional Name

[(2S,7Z,10R,13R,14Z,16R)-2,12-dihydroxy-4-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-1,13-dimethyl-6-oxo-5,17-dioxabicyclo[14.1.0]heptadeca-7,14-dien-10-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]/C(=C(/[H])\C(\C)=C(/[H])C1=COC(C)=N1)/C(/[H])=C(\C)[C@]([H])(OC)[C@@]([H])(C)C1([H])C[C@]([H])(O)C2(C)O[C@]2([H])\C([H])=C([H])/[C@@]([H])(C)C([H])(O)C[C@]([H])(CC(O)=O)C\C([H])=C([H])/C(=O)O1

InChI Identifier

InChI=1S/C35H49NO9/c1-21(16-27-20-43-25(5)36-27)10-8-11-23(3)34(42-7)24(4)29-19-30(38)35(6)31(45-35)15-14-22(2)28(37)17-26(18-32(39)40)12-9-13-33(41)44-29/h8-11,13-16,20,22,24,26,28-31,34,37-38H,12,17-19H2,1-7H3,(H,39,40)/b10-8+,13-9-,15-14-,21-16+,23-11+/t22-,24+,26-,28?,29?,30+,31-,34+,35?/m1/s1

InChI Key

FAIGGHHPKTYDHM-VRAWKDPKSA-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
Macrolide
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
2,4-disubstituted 1,3-oxazole
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxazole
Azole
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	4.5	ALOGPS
logP	4.07	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	0.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	151.85 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	173.91 m³·mol⁻¹	ChemAxon
Polarizability	68.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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	53.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	62.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	701.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	600.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	803.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	165.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3830.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	91.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	384.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	667.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	214.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	155.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	219.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	9.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	150.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	138.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	526.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1646.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1553.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Rhizoxin S2_TMS_1	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard non polar	2025-10-23	1630.2
Gas Chromatography	Rhizoxin S2_TMS_2	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard non polar	2025-10-23	1886.36
Gas Chromatography	Rhizoxin S2_TMS_3	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard non polar	2025-10-23	800.176
Gas Chromatography	Rhizoxin S2_TMS_4	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard non polar	2025-10-23	1048.5
Gas Chromatography	Rhizoxin S2_TMS_5	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard non polar	2025-10-23	2525.01
Gas Chromatography	Rhizoxin S2_TMS_6	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard non polar	2025-10-23	2095.95
Gas Chromatography	Rhizoxin S2_TMS_7	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard non polar	2025-10-23	1679.62
Gas Chromatography	Rhizoxin S2_TMS_1	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard polar	2025-10-23	2833.48
Gas Chromatography	Rhizoxin S2_TMS_2	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard polar	2025-10-23	1831.32
Gas Chromatography	Rhizoxin S2_TMS_3	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard polar	2025-10-23	2318.36
Gas Chromatography	Rhizoxin S2_TMS_4	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O)C/C=C\C(=O)O1	standard polar	2025-10-23	2527.32
Gas Chromatography	Rhizoxin S2_TMS_5	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard polar	2025-10-23	2548.98
Gas Chromatography	Rhizoxin S2_TMS_6	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard polar	2025-10-23	1276.94
Gas Chromatography	Rhizoxin S2_TMS_7	CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)C1C[C@H](O[Si](C)(C)C)C2(C)O[C@@H]2/C=C\[C@@H](C)C(O[Si](C)(C)C)C[C@H](CC(=O)O[Si](C)(C)C)C/C=C\C(=O)O1	standard polar	2025-10-23	1720.66

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	Proteobacteria	1	Human	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

78445096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584540

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 Rhizoxin S2 (MMDBc0005835)

MOL for #<Metabolite:0x00007f9a89852958>

3D MOL for #<Metabolite:0x00007f9a89852958>

3D SDF for #<Metabolite:0x00007f9a89852958>

3D-SDF for #<Metabolite:0x00007f9a89852958>

PDB for #<Metabolite:0x00007f9a89852958>

3D PDB for #<Metabolite:0x00007f9a89852958>

SMILES for #<Metabolite:0x00007f9a89852958>

INCHI for #<Metabolite:0x00007f9a89852958>

Structure for #<Metabolite:0x00007f9a89852958>

3D Structure for #<Metabolite:0x00007f9a89852958>