MiMeDB: Showing metabocard for Terreulactone A (MMDBc0018596)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 08:46:35 UTC

Update Date

2025-10-07 16:06:51 UTC

Metabolite ID

MMDBc0018596

Metabolite Identification

Common Name

Terreulactone A

Description

Terreulactone A is a polyketide, a class of natural products characterized by their diverse structures and biological activities. Its chemical structure features a complex arrangement of rings, specifically the A, B, and C rings, which are integral to its molecular identity. The synthesis of terreulactone A has been the focus of research, highlighting methods for the rapid construction of these rings, as evidenced by studies that detail an efficient synthesis pathway (PMID:16435850 ). This compound is involved in various biochemical pathways, although specific biological significance is not the focus here. The intricate nature of its structure and the synthetic approaches developed for its assembly underscore the complexity and potential of terreulactone A within the realm of natural product chemistry. The ongoing exploration of its synthesis not only enhances our understanding of its chemical properties but also opens avenues for further investigation into its biological interactions and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152110462D          

 37 42  0  0  1  0            999 V2000
    1.6043    0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    2.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5394    3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121    1.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1802    2.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3985    1.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9666    2.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0251    2.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074    1.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8573    0.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0030    1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5758    2.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165    1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210    1.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2529    0.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5150    1.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254    2.0456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4184    0.9349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2482    1.2399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7439    1.4483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1327    0.3866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0757   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3340   -0.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3092    1.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3471    0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3622    2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6775   -0.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393    0.6259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    2.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    1.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 12 11  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 24  3  1  6  0  0  0
 24 11  1  0  0  0  0
 25  4  1  6  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 12  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 21  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 20  2  0  0  0  0
 30 21  2  0  0  0  0
 31 22  2  0  0  0  0
 26 32  1  1  0  0  0
 33  5  1  0  0  0  0
 33 16  1  0  0  0  0
 34  6  1  0  0  0  0
 28 34  1  1  0  0  0
 35 18  1  0  0  0  0
 35 20  1  0  0  0  0
 36 19  1  0  0  0  0
 36 24  1  0  0  0  0
 37 22  1  0  0  0  0
 27 37  1  1  0  0  0
M  END


  Mrv1652305152110462D          

 37 42  0  0  1  0            999 V2000
    1.6043    0.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938    2.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5394    3.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121    1.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1802    2.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3985    1.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9666    2.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049    2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0251    2.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6074    1.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8573    0.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0030    1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5758    2.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165    1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8210    1.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2529    0.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5150    1.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4254    2.0456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4184    0.9349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2482    1.2399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7439    1.4483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1327    0.3866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0757   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3340   -0.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3092    1.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3471    0.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3622    2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6775   -0.3014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393    0.6259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118    2.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797    1.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 12 11  1  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 24  3  1  6  0  0  0
 24 11  1  0  0  0  0
 25  4  1  6  0  0  0
 25 21  1  0  0  0  0
 26 14  1  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 12  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 21  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 20  2  0  0  0  0
 30 21  2  0  0  0  0
 31 22  2  0  0  0  0
 26 32  1  1  0  0  0
 33  5  1  0  0  0  0
 33 16  1  0  0  0  0
 34  6  1  0  0  0  0
 28 34  1  1  0  0  0
 35 18  1  0  0  0  0
 35 20  1  0  0  0  0
 36 19  1  0  0  0  0
 36 24  1  0  0  0  0
 37 22  1  0  0  0  0
 27 37  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0018596

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC=C(C=C1)C1=CC2=C(C[C@]3(O)[C@@]4(C)C(=O)[C@@]5(OC)C(=O)O[C@]4(CC[C@@]3(C)O2)C5(C)C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O9/c1-23(2)27-12-11-24(3)26(32,25(27,4)21(30)28(23,34-6)22(31)37-27)14-17-19(36-24)13-18(35-20(17)29)15-7-9-16(33-5)10-8-15/h7-10,13,32H,11-12,14H2,1-6H3/t24-,25-,26-,27-,28+/m1/s1

> <INCHI_KEY>
AOFMVUCAUSHJLI-FXGKLIOSSA-N

> <FORMULA>
C28H30O9

> <MOLECULAR_WEIGHT>
510.539

> <EXACT_MASS>
510.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.30814635039534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,13S,14R,16R)-13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.0^{1,14}.0^{4,13}.0^{6,11}]nonadeca-6(11),7-diene-10,15,17-trione

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.8287844433333342

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.966779754375509

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6881305354361507

> <JCHEM_POLAR_SURFACE_AREA>
117.59000000000002

> <JCHEM_REFRACTIVITY>
130.51909999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,13S,14R,16R)-13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.0^{1,14}.0^{4,13}.0^{6,11}]nonadeca-6(11),7-diene-10,15,17-trione

> <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       2.995   0.826   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.249   1.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.708   5.326   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.510   0.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.807   6.039   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.272  -0.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.209   2.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.403   4.642   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.677   2.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.871   5.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.236   4.831   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.780   4.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.467   3.711   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.200   1.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.072   3.138   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.008   4.069   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.668   1.741   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.604   2.672   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.999   3.246   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.805   0.703   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.730   0.369   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.961   2.348   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.709   1.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.394   3.819   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.514   1.745   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.063   2.314   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.255   2.703   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.114   0.722   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.475  -0.801   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.357  -1.038   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.577   2.415   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.248   0.786   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.476   4.535   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.265  -0.563   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.273   1.168   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.862   4.284   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.015   3.588   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   33                                                            
CONECT    6   34                                                            
CONECT    7    9   15                                                       
CONECT    8   10   15                                                       
CONECT    9    7   16                                                       
CONECT   10    8   16                                                       
CONECT   11   12   24                                                       
CONECT   12   11   27                                                       
CONECT   13   18   19                                                       
CONECT   14   17   26                                                       
CONECT   15    7    8   18                                                  
CONECT   16    9   10   33                                                  
CONECT   17   14   19   20                                                  
CONECT   18   13   15   35                                                  
CONECT   19   13   17   36                                                  
CONECT   20   17   29   35                                                  
CONECT   21   25   28   30                                                  
CONECT   22   28   31   37                                                  
CONECT   23    1    2   27   28                                             
CONECT   24    3   11   26   36                                             
CONECT   25    4   21   26   27                                             
CONECT   26   14   24   25   32                                             
CONECT   27   12   23   25   37                                             
CONECT   28   21   22   23   34                                             
CONECT   29   20                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   26                                                            
CONECT   33    5   16                                                       
CONECT   34    6   28                                                       
CONECT   35   18   20                                                       
CONECT   36   19   24                                                       
CONECT   37   22   27                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₃₀O₉

Average Mass

510.539

Monoisotopic Mass

510.188982546

IUPAC Name

(1R,4R,13S,14R,16R)-13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.0^{1,14}.0^{4,13}.0^{6,11}]nonadeca-6(11),7-diene-10,15,17-trione

Traditional Name

(1R,4R,13S,14R,16R)-13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.0^{1,14}.0^{4,13}.0^{6,11}]nonadeca-6(11),7-diene-10,15,17-trione

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC2=C(C[C@]3(O)[C@@]4(C)C(=O)[C@@]5(OC)C(=O)O[C@]4(CC[C@@]3(C)O2)C5(C)C)C(=O)O1

InChI Identifier

InChI=1S/C28H30O9/c1-23(2)27-12-11-24(3)26(32,25(27,4)21(30)28(23,34-6)22(31)37-27)14-17-19(36-24)13-18(35-20(17)29)15-7-9-16(33-5)10-8-15/h7-10,13,32H,11-12,14H2,1-6H3/t24-,25-,26-,27-,28+/m1/s1

InChI Key

AOFMVUCAUSHJLI-FXGKLIOSSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.83	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	130.52 m³·mol⁻¹	ChemAxon
Polarizability	53.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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_1_1) - 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)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

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 (void)	2025-10-23	111.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	42.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	456.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	500.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	633.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	190.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2511.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	203.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	333.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	411.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	282.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	171.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	210.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	12.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	254.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	81.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	335.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1304.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1011.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Terreulactone A_TMS_1	COC1=CC=C(C2=CC3=C(C[C@]4(O[Si](C)(C)C)[C@@]5(C)C(=O)[C@@]6(OC)C(=O)O[C@]5(CC[C@@]4(C)O3)C6(C)C)C(=O)O2)C=C1	standard non polar	2025-10-23	2173.96
Gas Chromatography	Terreulactone A_TMS_1	COC1=CC=C(C2=CC3=C(C[C@]4(O[Si](C)(C)C)[C@@]5(C)C(=O)[C@@]6(OC)C(=O)O[C@]5(CC[C@@]4(C)O3)C6(C)C)C(=O)O2)C=C1	standard polar	2025-10-23	1365.47

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
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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Terreulactone A (MMDBc0018596)

MOL for #<Metabolite:0x00007fc953226068>

3D MOL for #<Metabolite:0x00007fc953226068>

3D SDF for #<Metabolite:0x00007fc953226068>

3D-SDF for #<Metabolite:0x00007fc953226068>

PDB for #<Metabolite:0x00007fc953226068>

3D PDB for #<Metabolite:0x00007fc953226068>

SMILES for #<Metabolite:0x00007fc953226068>

INCHI for #<Metabolite:0x00007fc953226068>

Structure for #<Metabolite:0x00007fc953226068>

3D Structure for #<Metabolite:0x00007fc953226068>