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Showing metabocard for 1,2-Dehydrosalsolinol (HMDB0012490)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:35 UTC
Update Date2023-02-21 17:17:50 UTC
HMDB IDHMDB0012490
Secondary Accession Numbers
  • HMDB12490
Metabolite Identification
Common Name1,2-Dehydrosalsolinol
Description1,2-dehydrosalsolinol(1-methyl-6,7-dihydroxy-3,4-dihydroisoquinolines) is formed through the decarboxylation of salsolinol-1-carboxylic acid (1-methyl-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid), a novel endogenous catecholic adduct of dopamine and pyruvic acid, examined in nuclei-free homogenates of rat liver, whole brain, and kidney, as well as in buffer only. Liquid chromatographic analysis of incubations for varying times (30 min to 5 h) showed that the tetrahydroisoquinoline substrate decarboxylated oxidatively, forming the DSAL (PMID: 3369867 ). It is involved in Tyrosine Metabolism.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012490 (1,2-Dehydrosalsolinol)

  Mrv0541 02251208052D          

 13 14  0  0  0  0            999 V2000
   10.5972  -14.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5972  -15.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -15.5862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5972  -16.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0262  -16.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7401  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4546  -16.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7401  -15.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4546  -15.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0262  -15.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116  -15.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  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
  6  7  1  0  0  0  0
  6 13  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0012490 (1,2-Dehydrosalsolinol)

HMDB0012490
     RDKit          3D
1,2-Dehydrosalsolinol
 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.4726    2.5534   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    1.0772    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    0.3462    0.1647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -1.0576    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537   -1.8362    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381   -1.0227    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -1.6836    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -0.9889   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -1.6540   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254    0.3853   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    1.0804   -0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122    1.0271   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    0.3394   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571    3.0276    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845    2.9181    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    2.9079   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253   -1.3816   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -1.3274    1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.6045   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118   -2.4607    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702   -2.7585    0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648   -1.0895   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3545    2.0885   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254    2.1141   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  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
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0012490 (1,2-Dehydrosalsolinol)

  Mrv0541 02251208052D          

 13 14  0  0  0  0            999 V2000
   10.5972  -14.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5972  -15.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -15.5862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5972  -16.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0262  -16.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7401  -16.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4546  -16.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7401  -15.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4546  -15.1738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0262  -15.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116  -15.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  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
  6  7  1  0  0  0  0
  6 13  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012490

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NCCC2=C1C=C(O)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-5,12-13H,2-3H2,1H3

> <INCHI_KEY>
DWHSGRLKLUGKOU-UHFFFAOYSA-N

> <FORMULA>
C10H11NO2

> <MOLECULAR_WEIGHT>
177.1998

> <EXACT_MASS>
177.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.648669120621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-3,4-dihydroisoquinoline-6,7-diol

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.1999887766666666

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.584102243039545

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.310048643055536

> <JCHEM_PKA_STRONGEST_BASIC>
5.961874719530706

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
50.686

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-3,4-dihydroisoquinoline-6,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012490 (1,2-Dehydrosalsolinol)

HMDB0012490
     RDKit          3D
1,2-Dehydrosalsolinol
 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.4726    2.5534   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    1.0772    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    0.3462    0.1647 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089   -1.0576    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537   -1.8362    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381   -1.0227    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -1.6836    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -0.9889   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -1.6540   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254    0.3853   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    1.0804   -0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122    1.0271   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    0.3394   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571    3.0276    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845    2.9181    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    2.9079   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3253   -1.3816   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420   -1.3274    1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4137   -2.6045   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118   -2.4607    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1702   -2.7585    0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648   -1.0895   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3545    2.0885   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254    2.1141   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  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
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

PDB for HMDB0012490 (1,2-Dehydrosalsolinol)

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.781 -26.784   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.781 -28.324   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      18.448 -29.094   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      18.448 -30.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.781 -31.404   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.115 -30.634   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.449 -31.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.782 -30.634   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      25.115 -31.404   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      23.782 -29.094   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      25.115 -28.324   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      22.449 -28.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.115 -29.094   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13    2    6   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0012490 (1,2-Dehydrosalsolinol)

COMPND    HMDB0012490
HETATM    1  C1  UNL     1      -1.473   2.553  -0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.463   1.077   0.050  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.511   0.346   0.165  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.609  -1.058   0.244  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.354  -1.836   0.195  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.138  -1.023   0.062  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.113  -1.684   0.005  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.284  -0.989  -0.118  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.529  -1.654  -0.175  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.225   0.385  -0.185  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.412   1.080  -0.308  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.012   1.027  -0.129  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.187   0.339  -0.005  1.00  0.00           C  
HETATM   14  H1  UNL     1      -0.757   3.028   0.664  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.485   2.918   0.266  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.323   2.908  -1.085  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.325  -1.382  -0.576  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.142  -1.327   1.224  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.414  -2.605  -0.650  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.212  -2.461   1.124  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.170  -2.759   0.056  1.00  0.00           H  
HETATM   22  H9  UNL     1       4.365  -1.090  -0.265  1.00  0.00           H  
HETATM   23  H10 UNL     1       3.355   2.088  -0.356  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.925   2.114  -0.179  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   13
CONECT    3    4
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    7   13
CONECT    7    8   21
CONECT    8    9   10   10
CONECT    9   22
CONECT   10   11   12
CONECT   11   23
CONECT   12   13   13   24
END
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SMILES for HMDB0012490 (1,2-Dehydrosalsolinol)

CC1=NCCC2=C1C=C(O)C(O)=C2
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INCHI for HMDB0012490 (1,2-Dehydrosalsolinol)

InChI=1S/C10H11NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-5,12-13H,2-3H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Methyl-6,7-dihydroxy-3,4-dihydroisoquinolinesHMDB
3,4-dihydro-1-Methyl-6,7-isoquinolinediolHMDB
DSALHMDB
Chemical FormulaC10H11NO2
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
IUPAC Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
Traditional Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
CAS Registry Number4602-81-7
SMILES
CC1=NCCC2=C1C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C10H11NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-5,12-13H,2-3H2,1H3
InChI KeyDWHSGRLKLUGKOU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroisoquinolines. These are isoquinoline derivatives where exactly two carbon atoms joined by an aromatic bond are linked with a hydrogen atom each, resulting in a CC single bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydroisoquinolines
Sub ClassNot Available
Direct ParentDihydroisoquinolines
Alternative Parents
Substituents
  • Dihydroisoquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
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 IDFDB029097
KNApSAcK IDNot Available
Chemspider ID17960720
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20844
PDB IDNot Available
ChEBI ID193796
Food Biomarker OntologyNot Available
VMH IDCE5629
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Collins MA, Cheng BY: Oxidative decarboxylation of salsolinol-1-carboxylic acid to 1,2-dehydrosalsolinol: evidence for exclusive catalysis by particulate factors in rat kidney. Arch Biochem Biophys. 1988 May 15;263(1):86-95. [PubMed:3369867 ]