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Showing NP-Card for 4-Hydroxydebrisoquine (NP0087515)

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Record Information
Version2.0
Created at2022-05-11 16:51:51 UTC
Updated at2022-05-11 16:51:51 UTC
NP-MRD IDNP0087515
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxydebrisoquine
Description4-Hydroxydebrisoquine belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. 4-Hydroxydebrisoquine is a very strong basic compound (based on its pKa). 4-Hydroxydebrisoquine was first documented in 2005 (PMID: 15843230). An isoquinoline that is 3,4-dihydroisoquinoline bearing amidino and hydroxy substituent at positions 2 and 4 respectively.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087515 (4-Hydroxydebrisoquine)


  Mrv0541 02231220392D          

 14 15  0  0  0  0            999 V2000
   14.7344  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -10.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -12.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -12.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -13.7362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3068  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
M  END
Download

3D MOL for NP0087515 (4-Hydroxydebrisoquine)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -4.5087    0.5344    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074    0.7204    1.0605 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7890   -0.1067    0.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3624   -1.2545   -0.2622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    0.1057    0.1621 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399   -1.0674    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -0.7494    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -1.6077    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802   -1.3493    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5827   -0.1802    0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    0.6780   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024    0.4072   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3302    1.3584   -1.0164 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9506    2.5737   -1.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8969    1.4274   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122   -2.1430    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -1.1997   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957   -1.6395    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539   -1.7912   -0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -2.5237    1.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215   -1.9910    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6412    0.0555    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497    1.6032   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082    0.9396   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    3.2791   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6746    1.9706   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902    1.9502    0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  2  0
  3  5  1  0
  5 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12  7  2  0
  7  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  6  5  1  0
 11 12  1  0
  4 16  1  0
  4 17  1  0
  2  1  1  0
 15 26  1  0
 15 27  1  0
 13 24  1  6
 14 25  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0087515 (4-Hydroxydebrisoquine)


  Mrv0541 02231220392D          

 14 15  0  0  0  0            999 V2000
   14.7344  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -10.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -10.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4489  -12.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1634  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8779  -11.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7344  -12.9112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -12.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924  -13.7362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3068  -12.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=N)N1CC(O)C2=C(C1)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)

> <INCHI_KEY>
AKFURXZANOMQBD-UHFFFAOYSA-N

> <FORMULA>
C10H13N3O

> <MOLECULAR_WEIGHT>
191.2297

> <EXACT_MASS>
191.105862053

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.080777484710485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.05965590167281229

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.04029777171078

> <JCHEM_PKA_STRONGEST_BASIC>
12.087959589142267

> <JCHEM_POLAR_SURFACE_AREA>
73.34

> <JCHEM_REFRACTIVITY>
65.05780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxydebrisoquine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0087515 (4-Hydroxydebrisoquine)

Download
PDB for NP0087515 (4-Hydroxydebrisoquine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.504 -21.021   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.504 -19.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.838 -18.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.172 -19.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.172 -21.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.838 -21.791   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.838 -23.331   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.172 -24.101   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      31.505 -23.331   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.505 -21.791   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      27.504 -24.101   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.839 -24.101   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      32.839 -25.641   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      34.173 -23.331   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    5                                                       
CONECT   11    7                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0087515 (4-Hydroxydebrisoquine)
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SMILES for NP0087515 (4-Hydroxydebrisoquine)
NC(=N)N1CC(O)C2=C(C1)C=CC=C2
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INCHI for NP0087515 (4-Hydroxydebrisoquine)
InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)
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View in JSmol
Synonyms
ValueSource
3,4-Dihydro-4-hydroxy-2(1H)-isoquinolinecarboximidamideChEBI
4 Hydroxy debrisoquineHMDB
4-Hydroxydebrisoquin sulfate (2:1)HMDB
4-HydroxydebrisoquinHMDB
4-HydroxydebrisoquineMeSH
Chemical FormulaC10H13N3O
Average Mass191.2297 Da
Monoisotopic Mass191.10586 Da
IUPAC Name4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide
Traditional Name4-hydroxydebrisoquine
CAS Registry NumberNot Available
SMILES
NC(=N)N1CC(O)C2=C(C1)C=CC=C2
InChI Identifier
InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)
InChI KeyAKFURXZANOMQBD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassTetrahydroisoquinolines  
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines  
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
    • 

  • Benzenoid
    • 

  • Secondary alcohol
    • 

  • Guanidine
    • 

  • Azacycle
    • 

  • Carboximidamide
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Imine
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP-0.27ALOGPS
logP0.06ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)12.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.06 m³·mol⁻¹ChemAxon
Polarizability20.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006468  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023927  
KNApSAcK IDNot Available
Chemspider ID96842  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2299987  
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107669  
PDB IDNot Available
ChEBI ID63800  
Good Scents IDNot Available
References
General References
  1. Dorado P, Berecz R, Caceres MC, Gonzalez I, Cobaleda J, Llerena A: Determination of debrisoquine and 4-hydroxydebrisoquine by high-performance liquid chromatography: application to the evaluation of CYP2D6 genotype and debrisoquine metabolic ratio relationship. Clin Chem Lab Med. 2005;43(3):275-9. doi: 10.1515/CCLM.2005.046. [PubMed:15843230  ]