MiMeDB: Showing metabocard for Phomalide (MMDBc0014987)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:53:16 UTC

Update Date

2025-10-07 16:06:21 UTC

Metabolite ID

MMDBc0014987

Metabolite Identification

Common Name

Phomalide

Description

Phomalide is a cyclic depsipeptide belonging to the class of fungal phytotoxins. This metabolite is produced by the fungus Leptosphaeria maculans and is known for its host-selective phytotoxicity. In biological evaluations, phomalide has been shown to induce necrotic and chlorotic lesions on susceptible canola leaves (Brassica napus and Brassica rapa), while exhibiting significantly less phytotoxicity on resistant cultivars such as brown mustard (Brassica juncea) and white mustard (Sinapis alba) (PMID:30754782 ). The synthesis of phomalide, along with its isomer isophomalide and dihydro analogues, has been achieved through efficient total synthesis methods, highlighting its complex structure that includes specific amino acids such as 2-amino-2-butenoic acid and (2S)-2-hydroxy-3-phenylpropanoic acid (PMID:11674233 ). Notably, while phomalide exhibits phytotoxic properties, other related metabolites like sirodesmin PL and phomamide do not display similar stress-inducing activities (PMID:18701303 ). Overall, phomalide's unique chemical structure and its role as a host-selective toxin underscore its significance in plant-fungal interactions and potential implications in agricultural contexts.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107532D          

 45 46  0  0  1  0            999 V2000
    3.8846   -0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2959   -5.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -3.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098    1.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956    1.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -5.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -5.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -5.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -3.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244   -4.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -4.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -1.2467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1683   -3.2732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0453   -3.0182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5462    0.2606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7592   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814   -2.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    0.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -3.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -0.5793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098   -1.9141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0613   -0.4068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441    0.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -2.9761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    0.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4430   -1.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -4.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -3.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -2.1932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    0.5248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.0004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4448   -3.8252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -2.6057    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    0.3469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 17  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18 15  1  0  0  0  0
 19  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20 12  2  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21  8  2  0  0  0  0
 22 14  1  6  0  0  0
 23 15  1  1  0  0  0
 24 16  1  1  0  0  0
 25 19  1  1  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29 21  1  0  0  0  0
 30 24  1  0  0  0  0
 31 21  1  4  0  0  0
 31 28  2  0  0  0  0
 32 22  1  0  0  0  0
 32 27  2  0  0  0  0
 33 25  1  0  0  0  0
 33 26  2  0  0  0  0
 26 34  1  4  0  0  0
 27 35  1  4  0  0  0
 36 28  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
 39 23  1  0  0  0  0
 39 30  1  0  0  0  0
 40 24  1  0  0  0  0
 40 29  1  0  0  0  0
 41  8  1  0  0  0  0
 22 42  1  1  0  0  0
 23 43  1  6  0  0  0
 24 44  1  6  0  0  0
 25 45  1  6  0  0  0
M  END


  Mrv1652305152107532D          

 45 46  0  0  1  0            999 V2000
    3.8846   -0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2959   -5.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7375   -3.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098    1.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956    1.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -5.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -5.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -5.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -4.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -3.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244   -4.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2106    1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -4.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -0.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -1.2467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1683   -3.2732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0453   -3.0182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5462    0.2606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7592   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814   -2.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    0.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6584   -1.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -3.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -0.5793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098   -1.9141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0613   -0.4068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441    0.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -2.9761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516    0.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4430   -1.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308   -4.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -3.0182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0453   -2.1932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    0.5248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.0004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4448   -3.8252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598   -2.6057    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    0.3469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 17  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  0  0  0  0
 18  5  1  0  0  0  0
 18 15  1  0  0  0  0
 19  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20 12  2  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21  8  2  0  0  0  0
 22 14  1  6  0  0  0
 23 15  1  1  0  0  0
 24 16  1  1  0  0  0
 25 19  1  1  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 25  1  0  0  0  0
 29 21  1  0  0  0  0
 30 24  1  0  0  0  0
 31 21  1  4  0  0  0
 31 28  2  0  0  0  0
 32 22  1  0  0  0  0
 32 27  2  0  0  0  0
 33 25  1  0  0  0  0
 33 26  2  0  0  0  0
 26 34  1  4  0  0  0
 27 35  1  4  0  0  0
 36 28  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
 39 23  1  0  0  0  0
 39 30  1  0  0  0  0
 40 24  1  0  0  0  0
 40 29  1  0  0  0  0
 41  8  1  0  0  0  0
 22 42  1  1  0  0  0
 23 43  1  6  0  0  0
 24 44  1  6  0  0  0
 25 45  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014987

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C)=C1/N=C(O)[C@@]([H])(N=C(O)[C@@]([H])(CC(C)C)N=C(O)[C@]([H])(CC(C)C)OC(=O)[C@]([H])(CC2=CC=CC=C2)OC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H43N3O7/c1-8-21-29(37)40-24(16-20-12-10-9-11-13-20)30(38)39-23(15-18(4)5)27(35)32-22(14-17(2)3)26(34)33-25(19(6)7)28(36)31-21/h8-13,17-19,22-25H,14-16H2,1-7H3,(H,31,36)(H,32,35)(H,33,34)/b21-8+/t22-,23+,24+,25+/m1/s1

> <INCHI_KEY>
CFTIBXPRNRXQEG-TYHNAPLMSA-N

> <FORMULA>
C30H43N3O7

> <MOLECULAR_WEIGHT>
557.688

> <EXACT_MASS>
557.310100737

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.048077640873004

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6E,9S,12R,15S)-3-benzyl-6-ethylidene-8,11,14-trihydroxy-12,15-bis(2-methylpropyl)-9-(propan-2-yl)-1,4-dioxa-7,10,13-triazacyclopentadeca-7,10,13-triene-2,5-dione

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
5.500615687864044

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.575674496805127

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8817055177754072

> <JCHEM_PKA_STRONGEST_BASIC>
4.951112874526902

> <JCHEM_POLAR_SURFACE_AREA>
150.36999999999998

> <JCHEM_REFRACTIVITY>
151.2068

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6E,9S,12R,15S)-3-benzyl-6-ethylidene-8,11,14-trihydroxy-9-isopropyl-12,15-bis(2-methylpropyl)-1,4-dioxa-7,10,13-triazacyclopentadeca-7,10,13-triene-2,5-dione

> <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       7.251  -1.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.012  -1.403   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.854   0.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.419  -9.598   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.243  -7.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.138   2.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.298   3.139   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.787  -0.527   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.152 -11.024   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.485 -10.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.818 -10.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.485  -8.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.818  -8.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.575  -2.488   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.634  -7.616   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.152  -6.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.480  -1.242   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.099  -8.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.393   1.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.152  -7.944   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.642  -1.557   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.044  -2.327   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.314  -6.110   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.818  -5.634   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.020   0.487   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.417  -0.920   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.459  -5.079   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.551   0.326   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.962  -3.064   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.484  -6.404   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       3.178  -1.081   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      -1.138  -3.573   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       0.114  -0.759   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      -2.322   0.326   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.923  -5.555   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.456   1.571   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.427  -3.539   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.484  -7.944   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.151  -5.634   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       3.818  -4.094   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0       5.466   0.980   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.670  -3.734   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.830  -7.140   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.152  -4.864   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.512   0.648   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7   19                                                            
CONECT    8    1   21   41                                                  
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   20                                                       
CONECT   13   11   20                                                       
CONECT   14   17   22                                                       
CONECT   15   18   23                                                       
CONECT   16   20   24                                                       
CONECT   17    2    3   14                                                  
CONECT   18    4    5   15                                                  
CONECT   19    6    7   25                                                  
CONECT   20   12   13   16                                                  
CONECT   21    8   29   31                                                  
CONECT   22   14   26   32   42                                             
CONECT   23   15   27   39   43                                             
CONECT   24   16   30   40   44                                             
CONECT   25   19   28   33   45                                             
CONECT   26   22   33   34                                                  
CONECT   27   23   32   35                                                  
CONECT   28   25   31   36                                                  
CONECT   29   21   37   40                                                  
CONECT   30   24   38   39                                                  
CONECT   31   21   28                                                       
CONECT   32   22   27                                                       
CONECT   33   25   26                                                       
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   29                                                            
CONECT   38   30                                                            
CONECT   39   23   30                                                       
CONECT   40   24   29                                                       
CONECT   41    8                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   92    0
END

Synonyms

Not Available

Molecular Formula

C₃₀H₄₃N₃O₇

Average Mass

557.688

Monoisotopic Mass

557.310100737

IUPAC Name

(3S,6E,9S,12R,15S)-3-benzyl-6-ethylidene-8,11,14-trihydroxy-12,15-bis(2-methylpropyl)-9-(propan-2-yl)-1,4-dioxa-7,10,13-triazacyclopentadeca-7,10,13-triene-2,5-dione

Traditional Name

(3S,6E,9S,12R,15S)-3-benzyl-6-ethylidene-8,11,14-trihydroxy-9-isopropyl-12,15-bis(2-methylpropyl)-1,4-dioxa-7,10,13-triazacyclopentadeca-7,10,13-triene-2,5-dione

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C1/N=C(O)[C@@]([H])(N=C(O)[C@@]([H])(CC(C)C)N=C(O)[C@]([H])(CC(C)C)OC(=O)[C@]([H])(CC2=CC=CC=C2)OC1=O)C(C)C

InChI Identifier

InChI=1S/C30H43N3O7/c1-8-21-29(37)40-24(16-20-12-10-9-11-13-20)30(38)39-23(15-18(4)5)27(35)32-22(14-17(2)3)26(34)33-25(19(6)7)28(36)31-21/h8-13,17-19,22-25H,14-16H2,1-7H3,(H,31,36)(H,32,35)(H,33,34)/b21-8+/t22-,23+,24+,25+/m1/s1

InChI Key

CFTIBXPRNRXQEG-TYHNAPLMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
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	0.0054 g/L	ALOGPS
logP	3.96	ALOGPS
logP	5.5	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	0.88	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	151.21 m³·mol⁻¹	ChemAxon
Polarizability	59.05 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_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)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species

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
Eukaryota/Fungi	Ascomycota	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

9093971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10918719

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

References

Synthesis Reference

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 Phomalide (MMDBc0014987)

MOL for #<Metabolite:0x00007f2adcf5e6d8>

3D MOL for #<Metabolite:0x00007f2adcf5e6d8>

3D SDF for #<Metabolite:0x00007f2adcf5e6d8>

3D-SDF for #<Metabolite:0x00007f2adcf5e6d8>

PDB for #<Metabolite:0x00007f2adcf5e6d8>

3D PDB for #<Metabolite:0x00007f2adcf5e6d8>

SMILES for #<Metabolite:0x00007f2adcf5e6d8>

INCHI for #<Metabolite:0x00007f2adcf5e6d8>

Structure for #<Metabolite:0x00007f2adcf5e6d8>

3D Structure for #<Metabolite:0x00007f2adcf5e6d8>