MiMeDB: Showing metabocard for 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione (MMDBc0001117)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 18:43:52 UTC

Update Date

2025-10-07 16:04:25 UTC

Metabolite ID

MMDBc0001117

Metabolite Identification

Common Name

7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione

Description

7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione is a diketopiperazine alkaloid, a class of compounds known for their diverse biological activities. Its complex structure features a pyrazino[1,2-b]isoquinoline core, which is modified by hydroxy and methoxy groups, as well as an indole moiety, indicating potential interactions with biological pathways. The compound was identified in a study where MMAO1 using M2 medium yielded this metabolite, which includes the rare amino acid L-6,8-dihydroxy-7-methoxyphenylalanine (PMID:24116376 ). Such structural characteristics suggest that it may participate in various biochemical pathways, possibly influencing signaling mechanisms or metabolic processes in organisms. The presence of hydroxyl and methoxy groups could also imply antioxidant properties, enhancing its relevance in pharmacological research. Overall, this compound exemplifies the intricate relationship between chemical structure and biological function, warranting further investigation into its potential applications in medicinal chemistry.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142120432D          

 32 36  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -2.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860   -2.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -3.1201    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  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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
    3.5724   -0.4125    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    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
  5  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  4  2  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  5  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  1  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 14  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 21  2  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 25 22  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  1  1  0  0  0  0
 30 20  1  0  0  0  0
 16 31  1  6  0  0  0
 17 32  1  6  0  0  0
M  END


  Mrv1652305142120432D          

 32 36  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -2.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860   -2.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -1.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -3.1201    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  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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
    3.5724   -0.4125    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    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
  5  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  4  2  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  5  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  1  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 14  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22 16  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 21  2  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 25 22  1  0  0  0  0
 26 18  1  0  0  0  0
 27 19  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  1  1  0  0  0  0
 30 20  1  0  0  0  0
 16 31  1  6  0  0  0
 17 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001117

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(CC2=CNC3=CC=CC=C23)N=C(O)[C@@]2([H])CC3=CC(O)=C(OC)C(O)=C3CN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H21N3O5/c1-30-20-18(26)8-11-7-17-21(28)24-16(22(29)25(17)10-14(11)19(20)27)6-12-9-23-15-5-3-2-4-13(12)15/h2-5,8-9,16-17,23,26-27H,6-7,10H2,1H3,(H,24,28)/t16-,17-/m1/s1

> <INCHI_KEY>
FBGQHXBBNVDHIX-IAGOWNOFSA-N

> <FORMULA>
C22H21N3O5

> <MOLECULAR_WEIGHT>
407.426

> <EXACT_MASS>
407.148120788

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.03453278119203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,11aR)-1,7,9-trihydroxy-3-[(1H-indol-3-yl)methyl]-8-methoxy-3H,4H,6H,11H,11aH-pyrazino[1,2-b]isoquinolin-4-one

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.368082318666666

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.51943895008521

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.204889350148195

> <JCHEM_PKA_STRONGEST_BASIC>
0.8327616262381239

> <JCHEM_POLAR_SURFACE_AREA>
118.38000000000001

> <JCHEM_REFRACTIVITY>
109.31729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,11aR)-1,7,9-trihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-3H,6H,11H,11aH-pyrazino[1,2-b]isoquinolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.116  -4.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.640  -5.504   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.086  -2.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.134  -5.824   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.104  -4.680   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.564  -4.680   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -0.000   1.540   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1   30                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   15                                                       
CONECT    6   12   16                                                       
CONECT    7   11   17                                                       
CONECT    8   11   18                                                       
CONECT    9   12   23                                                       
CONECT   10   14   25                                                       
CONECT   11    7    8   14                                                  
CONECT   12    6    9   13                                                  
CONECT   13    4   12   15                                                  
CONECT   14   10   11   19                                                  
CONECT   15    5   13   23                                                  
CONECT   16    6   22   24   31                                             
CONECT   17    7   21   25   32                                             
CONECT   18    8   20   26                                                  
CONECT   19   14   20   27                                                  
CONECT   20   18   19   30                                                  
CONECT   21   17   24   28                                                  
CONECT   22   16   25   29                                                  
CONECT   23    9   15                                                       
CONECT   24   16   21                                                       
CONECT   25   10   17   22                                                  
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30    1   20                                                       
CONECT   31   16                                                            
CONECT   32   17                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

Synonyms

Value	Source
7,9-Dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino(1,2-b)isoquinoline-1,4-dione	MeSH

Molecular Formula

C₂₂H₂₁N₃O₅

Average Mass

407.426

Monoisotopic Mass

407.148120788

IUPAC Name

(3R,11aR)-1,7,9-trihydroxy-3-[(1H-indol-3-yl)methyl]-8-methoxy-3H,4H,6H,11H,11aH-pyrazino[1,2-b]isoquinolin-4-one

Traditional Name

(3R,11aR)-1,7,9-trihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-3H,6H,11H,11aH-pyrazino[1,2-b]isoquinolin-4-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(CC2=CNC3=CC=CC=C23)N=C(O)[C@@]2([H])CC3=CC(O)=C(OC)C(O)=C3CN2C1=O

InChI Identifier

InChI=1S/C22H21N3O5/c1-30-20-18(26)8-11-7-17-21(28)24-16(22(29)25(17)10-14(11)19(20)27)6-12-9-23-15-5-3-2-4-13(12)15/h2-5,8-9,16-17,23,26-27H,6-7,10H2,1H3,(H,24,28)/t16-,17-/m1/s1

InChI Key

FBGQHXBBNVDHIX-IAGOWNOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

3-alkylindole
Tetrahydroisoquinoline
Alpha-amino acid or derivatives
Indole or derivatives
Indole
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrole
Lactam
Carboxamide group
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.085 g/L	ALOGPS
logP	1.92	ALOGPS
logP	2.37	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.32 m³·mol⁻¹	ChemAxon
Polarizability	42.03 Å³	ChemAxon
Number of Rings	5	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_2_2) - 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)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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	163.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	39.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	401.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	368.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	415.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	186.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1858.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	136.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	248.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	170.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	222.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	152.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	136.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	107.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	281.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	124.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	304.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1180.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	798.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_1	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	1438.83
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_2	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	2489.0
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_3	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	2069.12
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_4	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	1491.4
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_5	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	2382.3
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_6	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	2469.0
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_7	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	1931.88
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_8	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	2849.71
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_9	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	1091.62
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_10	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	2220.77
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_11	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	1498.93
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_12	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard non polar	2025-10-23	3436.72
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_13	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	1512.84
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_14	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	1498.68
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_15	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard non polar	2025-10-23	1442.34
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_1	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	1479.08
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_2	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	1666.98
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_3	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	2711.55
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_4	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	2071.26
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_5	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	3060.72
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_6	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	2729.68
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_7	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	2555.31
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_8	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	1877.69
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_9	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	2003.29
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_10	COC1=C(O)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	1602.17
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_11	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=C[NH]C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	1936.15
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_12	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O	standard polar	2025-10-23	1956.45
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_13	COC1=C(O)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	2051.52
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_14	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	2341.32
Gas Chromatography	7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione_TMS_15	COC1=C(O[Si](C)(C)C)C=C2C[C@@H]3C(O[Si](C)(C)C)=N[C@H](CC4=CN([Si](C)(C)C)C5=CC=CC=C45)C(=O)N3CC2=C1O[Si](C)(C)C	standard polar	2025-10-23	1511.65

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	2	Human feces; Human sputum; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32033836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583167

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 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione (MMDBc0001117)

MOL for #<Metabolite:0x000056431eb61518>

3D MOL for #<Metabolite:0x000056431eb61518>

3D SDF for #<Metabolite:0x000056431eb61518>

3D-SDF for #<Metabolite:0x000056431eb61518>

PDB for #<Metabolite:0x000056431eb61518>

3D PDB for #<Metabolite:0x000056431eb61518>

SMILES for #<Metabolite:0x000056431eb61518>

INCHI for #<Metabolite:0x000056431eb61518>

Structure for #<Metabolite:0x000056431eb61518>

3D Structure for #<Metabolite:0x000056431eb61518>