MiMeDB: Showing metabocard for Isosecosterigmatocystin (MMDBc0021751)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 11:54:17 UTC

Update Date

2025-10-07 16:07:09 UTC

Metabolite ID

MMDBc0021751

Metabolite Identification

Common Name

Isosecosterigmatocystin

Description

Isosecosterigmatocystin is a xanthone analog, a chemical class characterized by a specific polycyclic aromatic structure. Its chemical structure features a fused ring system that is typical of xanthones, which are known for their diverse biological activities. Isosecosterigmatocystin was isolated from the culture broth and mycelia extracts of the mangrove-derived endophytic fungus Aspergillus nidulans MA-143 under 0.1% ethanol stress, alongside other metabolites such as isoversicolorin C and glulisine A (PM...). This compound may play a role in various biochemical pathways, particularly those related to fungal secondary metabolism, which often involves the production of bioactive compounds. The presence of iso secosterigmatocystin in the metabolic profile of Aspergillus nidulans suggests its potential involvement in stress response mechanisms, possibly aiding the fungus in adapting to its environment. Further studies could elucidate its specific functions and interactions within the biosynthetic pathways of this organism.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152113542D          

 28 30  0  0  1  0            999 V2000
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    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
   -0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    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
    0.7145    2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  6  1  6  0  0  0
  9  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  6  1  0  0  0  0
 20  7  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 11 23  1  6  0  0  0
 24 17  2  0  0  0  0
 25  1  1  0  0  0  0
 25 13  1  0  0  0  0
 26 12  1  0  0  0  0
 26 18  1  0  0  0  0
  8 27  1  1  0  0  0
 11 28  1  1  0  0  0
M  END


  Mrv1652305152113542D          

 28 30  0  0  1  0            999 V2000
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    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
   -0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    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
    0.7145    2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  6  1  6  0  0  0
  9  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  6  1  0  0  0  0
 20  7  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 11 23  1  6  0  0  0
 24 17  2  0  0  0  0
 25  1  1  0  0  0  0
 25 13  1  0  0  0  0
 26 12  1  0  0  0  0
 26 18  1  0  0  0  0
  8 27  1  1  0  0  0
 11 28  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0021751

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CO)[C@]([H])(CO)C1=C2OC3=CC=CC(O)=C3C(=O)C2=C(OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O8/c1-25-13-5-10(22)14(8(6-19)11(23)7-20)18-16(13)17(24)15-9(21)3-2-4-12(15)26-18/h2-5,8,11,19-23H,6-7H2,1H3/t8-,11+/m0/s1

> <INCHI_KEY>
WHNAJPFARNBVDZ-GZMMTYOYSA-N

> <FORMULA>
C18H18O8

> <MOLECULAR_WEIGHT>
362.334

> <EXACT_MASS>
362.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.195455678620405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-1-methoxy-4-[(2S,3S)-1,3,4-trihydroxybutan-2-yl]-9H-xanthen-9-one

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
0.7056657436666667

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.525158651426496

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.668221402959179

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7338543758994316

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
91.07620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-1-methoxy-4-[(2S,3S)-1,3,4-trihydroxybutan-2-yl]xanthen-9-one

> <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   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667  12.320   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001  10.010   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.335   7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.000   7.700   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       1.334   3.850   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.667   6.160   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   12                                                       
CONECT    5   10   13                                                       
CONECT    6    8   19                                                       
CONECT    7   11   20                                                       
CONECT    8    6   11   14   27                                             
CONECT    9    3   15   21                                                  
CONECT   10    5   14   22                                                  
CONECT   11    7    8   23   28                                             
CONECT   12    4   15   26                                                  
CONECT   13    5   16   25                                                  
CONECT   14    8   10   18                                                  
CONECT   15    9   12   17                                                  
CONECT   16   13   17   18                                                  
CONECT   17   15   16   24                                                  
CONECT   18   14   16   26                                                  
CONECT   19    6                                                            
CONECT   20    7                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   17                                                            
CONECT   25    1   13                                                       
CONECT   26   12   18                                                       
CONECT   27    8                                                            
CONECT   28   11                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₁₈O₈

Average Mass

362.334

Monoisotopic Mass

362.10016754

IUPAC Name

3,8-dihydroxy-1-methoxy-4-[(2S,3S)-1,3,4-trihydroxybutan-2-yl]-9H-xanthen-9-one

Traditional Name

3,8-dihydroxy-1-methoxy-4-[(2S,3S)-1,3,4-trihydroxybutan-2-yl]xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)[C@]([H])(CO)C1=C2OC3=CC=CC(O)=C3C(=O)C2=C(OC)C=C1O

InChI Identifier

InChI=1S/C18H18O8/c1-25-13-5-10(22)14(8(6-19)11(23)7-20)18-16(13)17(24)15-9(21)3-2-4-12(15)26-18/h2-5,8,11,19-23H,6-7H2,1H3/t8-,11+/m0/s1

InChI Key

WHNAJPFARNBVDZ-GZMMTYOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
1,2-diol
Secondary alcohol
Oxacycle
Ether
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Organic oxide
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	0.62 g/L	ALOGPS
logP	0.57	ALOGPS
logP	0.71	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.08 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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_5) - 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)		2022-08-20	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

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	182.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	83.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	361.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	408.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	368.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	201.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1781.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	256.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	341.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	175.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	194.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	157.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	114.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	161.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	387.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	99.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	280.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1350.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	710.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Isosecosterigmatocystin_TMS_1	COC1=CC(O)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2613.39
Gas Chromatography	Isosecosterigmatocystin_TMS_2	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2099.71
Gas Chromatography	Isosecosterigmatocystin_TMS_3	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2608.81
Gas Chromatography	Isosecosterigmatocystin_TMS_4	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1452.24
Gas Chromatography	Isosecosterigmatocystin_TMS_5	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1759.78
Gas Chromatography	Isosecosterigmatocystin_TMS_6	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2134.33
Gas Chromatography	Isosecosterigmatocystin_TMS_7	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2964.48
Gas Chromatography	Isosecosterigmatocystin_TMS_8	COC1=CC(O)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1524.98
Gas Chromatography	Isosecosterigmatocystin_TMS_9	COC1=CC(O)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	2534.37
Gas Chromatography	Isosecosterigmatocystin_TMS_10	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1876.09
Gas Chromatography	Isosecosterigmatocystin_TMS_11	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2670.49
Gas Chromatography	Isosecosterigmatocystin_TMS_12	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	2619.31
Gas Chromatography	Isosecosterigmatocystin_TMS_13	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1854.31
Gas Chromatography	Isosecosterigmatocystin_TMS_14	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1812.94
Gas Chromatography	Isosecosterigmatocystin_TMS_15	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1783.82
Gas Chromatography	Isosecosterigmatocystin_TMS_16	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2714.74
Gas Chromatography	Isosecosterigmatocystin_TMS_17	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1719.89
Gas Chromatography	Isosecosterigmatocystin_TMS_18	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1613.27
Gas Chromatography	Isosecosterigmatocystin_TMS_19	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2349.86
Gas Chromatography	Isosecosterigmatocystin_TMS_20	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1753.74
Gas Chromatography	Isosecosterigmatocystin_TMS_21	COC1=CC(O)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	3217.2
Gas Chromatography	Isosecosterigmatocystin_TMS_22	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	2233.33
Gas Chromatography	Isosecosterigmatocystin_TMS_23	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1736.29
Gas Chromatography	Isosecosterigmatocystin_TMS_24	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1992.36
Gas Chromatography	Isosecosterigmatocystin_TMS_25	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1496.13
Gas Chromatography	Isosecosterigmatocystin_TMS_26	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard non polar	2025-10-23	1691.96
Gas Chromatography	Isosecosterigmatocystin_TMS_27	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1439.29
Gas Chromatography	Isosecosterigmatocystin_TMS_28	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	1951.11
Gas Chromatography	Isosecosterigmatocystin_TMS_29	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	2523.98
Gas Chromatography	Isosecosterigmatocystin_TMS_30	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	2982.25
Gas Chromatography	Isosecosterigmatocystin_TMS_31	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard non polar	2025-10-23	3335.62
Gas Chromatography	Isosecosterigmatocystin_TMS_1	COC1=CC(O)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	1571.42
Gas Chromatography	Isosecosterigmatocystin_TMS_2	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2365.15
Gas Chromatography	Isosecosterigmatocystin_TMS_3	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2301.79
Gas Chromatography	Isosecosterigmatocystin_TMS_4	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1563.19
Gas Chromatography	Isosecosterigmatocystin_TMS_5	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2600.64
Gas Chromatography	Isosecosterigmatocystin_TMS_6	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	1364.82
Gas Chromatography	Isosecosterigmatocystin_TMS_7	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2810.83
Gas Chromatography	Isosecosterigmatocystin_TMS_8	COC1=CC(O)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2284.94
Gas Chromatography	Isosecosterigmatocystin_TMS_9	COC1=CC(O)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2553.41
Gas Chromatography	Isosecosterigmatocystin_TMS_10	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	1904.64
Gas Chromatography	Isosecosterigmatocystin_TMS_11	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2271.66
Gas Chromatography	Isosecosterigmatocystin_TMS_12	COC1=CC(O)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2117.71
Gas Chromatography	Isosecosterigmatocystin_TMS_13	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	3458.93
Gas Chromatography	Isosecosterigmatocystin_TMS_14	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	3015.67
Gas Chromatography	Isosecosterigmatocystin_TMS_15	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1240.2
Gas Chromatography	Isosecosterigmatocystin_TMS_16	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	3243.84
Gas Chromatography	Isosecosterigmatocystin_TMS_17	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2806.46
Gas Chromatography	Isosecosterigmatocystin_TMS_18	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2085.97
Gas Chromatography	Isosecosterigmatocystin_TMS_19	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	1083.49
Gas Chromatography	Isosecosterigmatocystin_TMS_20	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1564.75
Gas Chromatography	Isosecosterigmatocystin_TMS_21	COC1=CC(O)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1443.28
Gas Chromatography	Isosecosterigmatocystin_TMS_22	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	1512.76
Gas Chromatography	Isosecosterigmatocystin_TMS_23	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1579.35
Gas Chromatography	Isosecosterigmatocystin_TMS_24	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2738.68
Gas Chromatography	Isosecosterigmatocystin_TMS_25	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1239.53
Gas Chromatography	Isosecosterigmatocystin_TMS_26	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O)C=CC=C1O2	standard polar	2025-10-23	2819.74
Gas Chromatography	Isosecosterigmatocystin_TMS_27	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	1684.45
Gas Chromatography	Isosecosterigmatocystin_TMS_28	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2539.52
Gas Chromatography	Isosecosterigmatocystin_TMS_29	COC1=CC(O)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2342.34
Gas Chromatography	Isosecosterigmatocystin_TMS_30	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2285.7
Gas Chromatography	Isosecosterigmatocystin_TMS_31	COC1=CC(O[Si](C)(C)C)=C([C@@H](CO[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)C2=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O2	standard polar	2025-10-23	2409.98

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

71044448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26204904

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

WHNAJPFARNBVDZ-GZMMTYOYSA-N

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 Isosecosterigmatocystin (MMDBc0021751)

MOL for #<Metabolite:0x00007f2de44d5738>

3D MOL for #<Metabolite:0x00007f2de44d5738>

3D SDF for #<Metabolite:0x00007f2de44d5738>

3D-SDF for #<Metabolite:0x00007f2de44d5738>

PDB for #<Metabolite:0x00007f2de44d5738>

3D PDB for #<Metabolite:0x00007f2de44d5738>

SMILES for #<Metabolite:0x00007f2de44d5738>

INCHI for #<Metabolite:0x00007f2de44d5738>

Structure for #<Metabolite:0x00007f2de44d5738>

3D Structure for #<Metabolite:0x00007f2de44d5738>