MiMeDB: Showing metabocard for Terrelumamide A (MMDBc0017377)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:46:29 UTC

Update Date

2025-10-07 16:06:40 UTC

Metabolite ID

MMDBc0017377

Metabolite Identification

Common Name

Terrelumamide A

Description

Terrelumamide A is a secondary metabolite belonging to the class of amides. It has been isolated from various fungal sources, including the thermophilic fungus Aspergillus terreus and the fungus LGO13, where it is found alongside other known compounds such as terrein and ergosterol (PMID:2 32 5">30602 32 5 ). The chemical structure of terrelumamide A features a complex arrangement of carbon, nitrogen, and oxygen atoms, typical of fungal metabolites, which often exhibit diverse biological activities. In terms of biochemical pathways, terrelumamide A may play a role in secondary metabolite biosynthesis and could be involved in the regulation of cellular processes due to its structural characteristics. The presence of terrelumamide A alongside other metabolites suggests potential interactions within metabolic networks, possibly influencing pathways related to stress response or competition among fungal species (PMID:2 ...). Overall, terrelumamide A exemplifies the intricate chemistry found in fungal metabolites and their potential roles in ecological interactions.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109462D          

 35 37  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 21  8  2  0  0  0  0
 21 15  1  0  0  0  0
 22 12  2  0  0  0  0
 22 14  1  0  0  0  0
 23 11  1  4  0  0  0
 23 17  2  0  0  0  0
 13 24  1  6  0  0  0
 24 16  2  0  0  0  0
 25 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
  9 27  1  6  0  0  0
 16 28  1  4  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  2  0  0  0  0
 32 20  2  0  0  0  0
 33  3  1  0  0  0  0
 33 19  1  0  0  0  0
  9 34  1  6  0  0  0
 13 35  1  1  0  0  0
M  END


  Mrv1652305152109462D          

 35 37  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 21  8  2  0  0  0  0
 21 15  1  0  0  0  0
 22 12  2  0  0  0  0
 22 14  1  0  0  0  0
 23 11  1  4  0  0  0
 23 17  2  0  0  0  0
 13 24  1  6  0  0  0
 24 16  2  0  0  0  0
 25 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26 15  1  0  0  0  0
 26 20  1  0  0  0  0
  9 27  1  6  0  0  0
 16 28  1  4  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 31 19  2  0  0  0  0
 32 20  2  0  0  0  0
 33  3  1  0  0  0  0
 33 19  1  0  0  0  0
  9 34  1  6  0  0  0
 13 35  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017377

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O)[C@]([H])(N=C(O)C1=NC2=C(N=C1)N(C)C(=O)N=C2O)C(O)=NC1=CC=CC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N6O7/c1-9(27)13(17(29)23-11-7-5-4-6-10(11)19(31)33-3)24-16(28)12-8-21-15-14(22-12)18(30)25-20(32)26(15)2/h4-9,13,27H,1-3H3,(H,23,29)(H,24,28)(H,25,30,32)/t9-,13+/m1/s1

> <INCHI_KEY>
YVUJATOOBNWJDN-RNCFNFMXSA-N

> <FORMULA>
C20H20N6O7

> <MOLECULAR_WEIGHT>
456.415

> <EXACT_MASS>
456.139347008

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.43266283328502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-3-hydroxy-2-{[hydroxy(4-hydroxy-1-methyl-2-oxo-1,2-dihydropteridin-6-yl)methylidene]amino}-N-[2-(methoxycarbonyl)phenyl]butanimidic acid

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
1.3848964056666664

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.411191767379632

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.412697706597851

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5504458350264384

> <JCHEM_POLAR_SURFACE_AREA>
190.39

> <JCHEM_REFRACTIVITY>
114.56489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-hydroxy-2-{[hydroxy(4-hydroxy-1-methyl-2-oxopteridin-6-yl)methylidene]amino}-N-[2-(methoxycarbonyl)phenyl]butanimidic 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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      -6.668   2.310   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -2.667   1.540   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -5.335   3.080   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   26                                                            
CONECT    3   33                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8   12   21                                                       
CONECT    9    1   13   27   34                                             
CONECT   10    6   11   19                                                  
CONECT   11    7   10   23                                                  
CONECT   12    8   16   22                                                  
CONECT   13    9   17   24   35                                             
CONECT   14   15   18   22                                                  
CONECT   15   14   21   26                                                  
CONECT   16   12   24   28                                                  
CONECT   17   13   23   29                                                  
CONECT   18   14   25   30                                                  
CONECT   19   10   31   33                                                  
CONECT   20   25   26   32                                                  
CONECT   21    8   15                                                       
CONECT   22   12   14                                                       
CONECT   23   11   17                                                       
CONECT   24   13   16                                                       
CONECT   25   18   20                                                       
CONECT   26    2   15   20                                                  
CONECT   27    9                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33    3   19                                                       
CONECT   34    9                                                            
CONECT   35   13                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₂₀N₆O₇

Average Mass

456.415

Monoisotopic Mass

456.139347008

IUPAC Name

(2S,3R)-3-hydroxy-2-{[hydroxy(4-hydroxy-1-methyl-2-oxo-1,2-dihydropteridin-6-yl)methylidene]amino}-N-[2-(methoxycarbonyl)phenyl]butanimidic acid

Traditional Name

(2S,3R)-3-hydroxy-2-{[hydroxy(4-hydroxy-1-methyl-2-oxopteridin-6-yl)methylidene]amino}-N-[2-(methoxycarbonyl)phenyl]butanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O)[C@]([H])(N=C(O)C1=NC2=C(N=C1)N(C)C(=O)N=C2O)C(O)=NC1=CC=CC=C1C(=O)OC

InChI Identifier

InChI=1S/C20H20N6O7/c1-9(27)13(17(29)23-11-7-5-4-6-10(11)19(31)33-3)24-16(28)12-8-21-15-14(22-12)18(30)25-20(32)26(15)2/h4-9,13,27H,1-3H3,(H,23,29)(H,24,28)(H,25,30,32)/t9-,13+/m1/s1

InChI Key

YVUJATOOBNWJDN-RNCFNFMXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Not Available

Direct Parent

Pteridines and derivatives

Alternative Parents

Substituents

Pteridine
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Hydroxypyrimidine
Pyrimidone
Benzenoid
Pyrimidine
Pyrazine
Monocyclic benzene moiety
Heteroaromatic compound
Methyl ester
Secondary alcohol
Carboxylic acid ester
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	0.084 g/L	ALOGPS
logP	0.3	ALOGPS
logP	1.38	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	190.39 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.56 m³·mol⁻¹	ChemAxon
Polarizability	44.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	24.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	40.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	407.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	459.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	383.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	189.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2046.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	75.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	419.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	196.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	123.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	144.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	126.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	91.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	285.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	74.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	319.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1197.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	827.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Terrelumamide A_TMS_1	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	1892.64
Gas Chromatography	Terrelumamide A_TMS_2	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	1981.81
Gas Chromatography	Terrelumamide A_TMS_3	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	2481.86
Gas Chromatography	Terrelumamide A_TMS_4	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	618.94
Gas Chromatography	Terrelumamide A_TMS_5	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	2119.56
Gas Chromatography	Terrelumamide A_TMS_6	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	2752.25
Gas Chromatography	Terrelumamide A_TMS_7	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	2837.23
Gas Chromatography	Terrelumamide A_TMS_8	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	1461.83
Gas Chromatography	Terrelumamide A_TMS_9	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	2092.42
Gas Chromatography	Terrelumamide A_TMS_10	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	2759.85
Gas Chromatography	Terrelumamide A_TMS_11	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	1725.07
Gas Chromatography	Terrelumamide A_TMS_12	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	2008.95
Gas Chromatography	Terrelumamide A_TMS_13	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	1901.58
Gas Chromatography	Terrelumamide A_TMS_14	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard non polar	2025-10-23	2550.38
Gas Chromatography	Terrelumamide A_TMS_15	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard non polar	2025-10-23	1101.28
Gas Chromatography	Terrelumamide A_TMS_1	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	1144.83
Gas Chromatography	Terrelumamide A_TMS_2	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2004.25
Gas Chromatography	Terrelumamide A_TMS_3	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2083.32
Gas Chromatography	Terrelumamide A_TMS_4	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	1456.11
Gas Chromatography	Terrelumamide A_TMS_5	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	2488.64
Gas Chromatography	Terrelumamide A_TMS_6	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	3066.87
Gas Chromatography	Terrelumamide A_TMS_7	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	2472.04
Gas Chromatography	Terrelumamide A_TMS_8	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2014.28
Gas Chromatography	Terrelumamide A_TMS_9	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2213.45
Gas Chromatography	Terrelumamide A_TMS_10	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2027.93
Gas Chromatography	Terrelumamide A_TMS_11	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	2614.34
Gas Chromatography	Terrelumamide A_TMS_12	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	1566.69
Gas Chromatography	Terrelumamide A_TMS_13	COC(=O)C1=CC=CC=C1N=C(O)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	1772.86
Gas Chromatography	Terrelumamide A_TMS_14	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O	standard polar	2025-10-23	2262.14
Gas Chromatography	Terrelumamide A_TMS_15	COC(=O)C1=CC=CC=C1N=C(O[Si](C)(C)C)[C@@H](N=C(O[Si](C)(C)C)C1=CN=C2C(=N1)C(O[Si](C)(C)C)=NC(=O)N2C)[C@@H](C)O[Si](C)(C)C	standard polar	2025-10-23	3331.52

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

35516822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587886

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 Terrelumamide A (MMDBc0017377)

MOL for #<Metabolite:0x00007f9aa0022550>

3D MOL for #<Metabolite:0x00007f9aa0022550>

3D SDF for #<Metabolite:0x00007f9aa0022550>

3D-SDF for #<Metabolite:0x00007f9aa0022550>

PDB for #<Metabolite:0x00007f9aa0022550>

3D PDB for #<Metabolite:0x00007f9aa0022550>

SMILES for #<Metabolite:0x00007f9aa0022550>

INCHI for #<Metabolite:0x00007f9aa0022550>

Structure for #<Metabolite:0x00007f9aa0022550>

3D Structure for #<Metabolite:0x00007f9aa0022550>