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Showing NP-Card for 1,2-Dehydrosalsolinol (NP0339015)

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Record Information
Version2.0
Created at2024-09-11 19:15:22 UTC
Updated at2024-09-11 19:15:22 UTC
NP-MRD IDNP0339015
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2-Dehydrosalsolinol
Description1,2-Dehydrosalsolinol, also known as DSAL, 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. 1,2-Dehydrosalsolinol is a very strong basic compound (based on its pKa). Liquid chromatographic analysis of incubations for varying times (30 min to 5 h) showed that the tetrahydroisoquinoline substrate decarboxylated oxidatively, forming the 1,2-Dehydrosalsolinol (PMID: 3369867 ). 1,2-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. 1,2-Dehydrosalsolinol was first documented in 1988 (PMID: 3369867). It is involved in Tyrosine Metabolism.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339015 (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
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3D MOL for NP0339015 (1,2-Dehydrosalsolinol)

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3D SDF for NP0339015 (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>
NP0339015

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0339015 (1,2-Dehydrosalsolinol)
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PDB for NP0339015 (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 NP0339015 (1,2-Dehydrosalsolinol)
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SMILES for NP0339015 (1,2-Dehydrosalsolinol)
CC1=NCCC2=C1C=C(O)C(O)=C2
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INCHI for NP0339015 (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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Synonyms
ValueSource
1-Methyl-6,7-dihydroxy-3,4-dihydroisoquinolinesHMDB
3,4-Dihydro-1-methyl-6,7-isoquinolinediolHMDB
DSALHMDB
Chemical FormulaC10H11NO2
Average Mass177.1998 Da
Monoisotopic Mass177.07898 Da
IUPAC Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
Traditional Name1-methyl-3,4-dihydroisoquinoline-6,7-diol
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.19ALOGPS
logP1.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)5.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.69 m³·mol⁻¹ChemAxon
Polarizability18.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012490  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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. doi:  10.1016/0003-9861(88)90616-9. [PubMed:3369867  ]