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Showing metabocard for Adrenochrome (HMDB0012884)

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enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:11 UTC
Update Date2023-02-21 17:17:51 UTC
HMDB IDHMDB0012884
Secondary Accession Numbers
  • HMDB12884
Metabolite Identification
Common NameAdrenochrome
DescriptionAdrenochrome (CAS: 54-06-8) belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Adrenochrome is a red-coloured oxidation product of adrenaline (epinephrine) that was first isolated and identified by Green and Richter in 1937 (PMID: 16746378 ). It is highly soluble in water. Adrenochrome can be synthesized from adrenalin via oxidation with silver oxide (PMID: 4581204 ).
Structure
Data?1676999871
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012884 (Adrenochrome)


  Mrv1652306152023362D          

 13 14  0  0  0  0            999 V2000
 9997.926110000.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9261 9998.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.356810000.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.642310000.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6423 9999.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3568 9998.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.855910000.3309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.071310000.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0713 9999.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8559 9998.9960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.3408 9999.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.110910001.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1109 9998.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  1  2  0  0  0  0
  5  2  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7 12  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
  6  9  2  0  0  0  0
  3  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0012884 (Adrenochrome)

HMDB0012884
     RDKit          3D
Adrenochrome
 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.5432   -2.1496    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.9184    0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.1372   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.3675   -0.0068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3773    2.4747   -0.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3025    0.9642   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    1.6836   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    0.9850   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976    1.6163   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -0.4690    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010   -1.0900    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4405   -1.1734    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.4864    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -2.5657    1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -1.9892    1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658   -2.8861   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141    0.1078   -0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.0001   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3870    1.6027    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209    2.2718   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    2.7797   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -2.2626    0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13  2  1  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  7 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0012884 (Adrenochrome)


  Mrv1652306152023362D          

 13 14  0  0  0  0            999 V2000
 9997.926110000.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9261 9998.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.356810000.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.642310000.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6423 9999.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3568 9998.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.855910000.3309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.071310000.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0713 9999.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8559 9998.9960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.3408 9999.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.110910001.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1109 9998.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  1  2  0  0  0  0
  5  2  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7 12  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
  6  9  2  0  0  0  0
  3  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012884

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C[C@H](O)C2=CC(=O)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m0/s1

> <INCHI_KEY>
RPHLQSHHTJORHI-VIFPVBQESA-N

> <FORMULA>
C9H9NO3

> <MOLECULAR_WEIGHT>
179.175

> <EXACT_MASS>
179.058243154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.330866954230814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
-0.31307499066666655

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.092155605532412

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6240891513198132

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
48.556000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-hydroxy-1-methyl-2,3-dihydroindole-5,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012884 (Adrenochrome)

HMDB0012884
     RDKit          3D
Adrenochrome
 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.5432   -2.1496    0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707   -0.9184    0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.1372   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    1.3675   -0.0068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3773    2.4747   -0.7997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3025    0.9642   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    1.6836   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    0.9850   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7976    1.6163   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -0.4690    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010   -1.0900    0.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4405   -1.1734    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.4864    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -2.5657    1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5036   -1.9892    1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658   -2.8861   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141    0.1078   -0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.0001   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3870    1.6027    1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209    2.2718   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    2.7797   -0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -2.2626    0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13  2  1  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  7 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0012884 (Adrenochrome)

HEADER    PROTEIN                                 15-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-20         0                                  
HETATM    1  O   UNK     0    8662.7958667.576   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8662.7958664.497   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8665.4668667.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.1328666.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.1328665.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.4668664.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.2648667.284   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.8008666.808   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.8008665.269   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8668.2648664.793   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8669.1698666.038   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8668.7408668.749   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8668.7408663.328   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    4    8                                                       
CONECT    4    3    5    1                                                  
CONECT    5    4    6    2                                                  
CONECT    6    5    9                                                       
CONECT    7    8   11   12                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10    6                                                  
CONECT   10    9   11   13                                                  
CONECT   11    7   10                                                       
CONECT   12    7                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0012884 (Adrenochrome)

COMPND    HMDB0012884
HETATM    1  C1  UNL     1      -1.543  -2.150   0.756  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.071  -0.918   0.180  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.845   0.137  -0.441  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.125   1.368  -0.007  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.377   2.475  -0.800  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.303   0.964  -0.012  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.430   1.684  -0.102  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.702   0.985  -0.078  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.798   1.616  -0.159  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.709  -0.469   0.042  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.801  -1.090   0.065  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.440  -1.173   0.135  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.302  -0.486   0.108  1.00  0.00           C  
HETATM   14  H1  UNL     1      -0.797  -2.566   1.472  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.504  -1.989   1.300  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.766  -2.886  -0.059  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.914   0.108  -0.174  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.716  -0.000  -1.552  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.387   1.603   1.041  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.221   2.272  -1.751  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.388   2.780  -0.191  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.394  -2.263   0.226  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13
CONECT    3    4   17   18
CONECT    4    5    6   19
CONECT    5   20
CONECT    6    7    7   13
CONECT    7    8   21
CONECT    8    9    9   10
CONECT   10   11   11   12
CONECT   12   13   13   22
END
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SMILES for HMDB0012884 (Adrenochrome)

CN1C[C@H](O)C2=CC(=O)C(=O)C=C12
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INCHI for HMDB0012884 (Adrenochrome)

InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(-)-AdrenochromeHMDB
(3R)-2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dioneHMDB
(3R)-3-Hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dioneHMDB
(R)-3-Hydroxy-1-methyl-indoline-5,6-dioneHMDB
1-Methyl-3-hydroxy-5,6-dioxo-2,3,5,6-tetrahydroindoleHMDB
2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dioneHMDB
2,3-Dihydro-3-hydroxy-N-methylindole-5,6-quinoneHMDB
3-Hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dioneHMDB
3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dioneHMDB
3-Hydroxy-1-methyl-2,3-dihydroindole-5,6-dioneHMDB
3-Hydroxy-1-methyl-5,6-indolinedioneHMDB
AdChrHMDB
AdrenochromeHMDB
Chemical FormulaC9H9NO3
Average Molecular Weight179.175
Monoisotopic Molecular Weight179.058243154
IUPAC Name(3R)-3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
Traditional Name(3R)-3-hydroxy-1-methyl-2,3-dihydroindole-5,6-dione
CAS Registry Number7506-92-5
SMILES
CN1C[C@H](O)C2=CC(=O)C(=O)C=C12
InChI Identifier
InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3/t9-/m0/s1
InChI KeyRPHLQSHHTJORHI-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassNot Available
Direct ParentIndoles and derivatives
Alternative Parents
Substituents
  • Indole or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Vinylogous amide
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Enamine
  • Azacycle
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility68 g/LALOGPS
logP0.08ALOGPS
logP-0.31ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.56 m³·mol⁻¹ChemAxon
Polarizability17.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-172.24430932474
DeepCCS[M+Na]+147.13330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.9 minutes32390414
Predicted by Siyang on May 30, 20228.7422 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.2 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid498.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid284.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid69.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid177.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid43.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid255.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid263.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)677.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid592.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid38.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid823.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid187.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid183.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate610.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA377.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water237.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C122973.8Standard polar33892256
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C121706.1Standard non polar33892256
AdrenochromeCN1C[C@H](O)C2=CC(=O)C(=O)C=C121964.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adrenochrome,1TMS,isomer #1CN1C[C@H](O[Si](C)(C)C)C2=CC(=O)C(=O)C=C211996.9Semi standard non polar33892256
Adrenochrome,1TBDMS,isomer #1CN1C[C@H](O[Si](C)(C)C(C)(C)C)C2=CC(=O)C(=O)C=C212223.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029199
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdrenochrome
METLIN IDNot Available
PubChem Compound24884154
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Green DE, Richter D: Adrenaline and adrenochrome. Biochem J. 1937 Apr;31(4):596-616. doi: 10.1042/bj0310596. [PubMed:16746378 ]
  2. Heacock RA, Powell WS: Adrenochrome and related compounds. Prog Med Chem. 1972;9(2):275-339. doi: 10.1016/s0079-6468(08)70401-6. [PubMed:4581204 ]

Enzymes

Enzyme Details
1. Glutathione S-transferase theta-2
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a sulfatase activity.
Gene Name:
GSTT2
Uniprot ID:
P0CG29
Molecular weight:
Not Available