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Showing metabocard for Isoquinoline (HMDB0034244)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:02:51 UTC
Update Date2023-02-21 17:24:05 UTC
HMDB IDHMDB0034244
Secondary Accession Numbers
  • HMDB34244
Metabolite Identification
Common NameIsoquinoline
DescriptionIsoquinoline is a flavouring agent Being an analog of pyridine, isoquinoline is a weak base, with a pKb of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative. Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine and morphine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine
Structure
Data?1677000245
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034244 (Isoquinoline)

  Mrv1652303202018592D          

 10 11  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    1.4289    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
M  END
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3D MOL for HMDB0034244 (Isoquinoline)

HMDB0034244
     RDKit          3D
Isoquinoline
 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.0730    0.9144   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2245   -0.4563   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -1.3048   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -0.7862   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2176   -1.6417    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4327   -1.0760    0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908    0.2464    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5072    1.0967    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.5825    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    1.4444    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    1.5461   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -0.8618   -0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -2.3728   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -2.7129   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702    0.7055    0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    2.1605    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059    2.5162    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0034244 (Isoquinoline)

  Mrv1652303202018592D          

 10 11  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    1.4289    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  8  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034244

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2C=NC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H

> <INCHI_KEY>
AWJUIBRHMBBTKR-UHFFFAOYSA-N

> <FORMULA>
C9H7N

> <MOLECULAR_WEIGHT>
129.1586

> <EXACT_MASS>
129.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.850365607593725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
isoquinoline

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.7450501456666665

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.262251802823965

> <JCHEM_POLAR_SURFACE_AREA>
12.89

> <JCHEM_REFRACTIVITY>
40.351299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoquinoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034244 (Isoquinoline)

HMDB0034244
     RDKit          3D
Isoquinoline
 17 18  0  0  0  0  0  0  0  0999 V2000
   -2.0730    0.9144   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2245   -0.4563   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -1.3048   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -0.7862   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2176   -1.6417    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4327   -1.0760    0.2607 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908    0.2464    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5072    1.0967    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.5825    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    1.4444    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489    1.5461   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -0.8618   -0.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -2.3728   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -2.7129   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702    0.7055    0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    2.1605    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059    2.5162    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0034244 (Isoquinoline)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    9   10                                                       
CONECT    8    3    5    9                                                  
CONECT    9    4    7    8                                                  
CONECT   10    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0034244 (Isoquinoline)

COMPND    HMDB0034244
HETATM    1  C1  UNL     1      -2.073   0.914  -0.222  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.224  -0.456  -0.360  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.146  -1.305  -0.276  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.122  -0.786  -0.049  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.218  -1.642   0.037  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.433  -1.076   0.261  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.591   0.246   0.396  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.507   1.097   0.311  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.251   0.582   0.086  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.825   1.444   0.003  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.949   1.546  -0.296  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.218  -0.862  -0.538  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.251  -2.373  -0.382  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.093  -2.713  -0.071  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.570   0.705   0.576  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.608   2.161   0.415  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.706   2.516   0.111  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4   13
CONECT    4    5    9
CONECT    5    6    6   14
CONECT    6    7
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10
CONECT   10   17
END
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SMILES for HMDB0034244 (Isoquinoline)

C1=CC=C2C=NC=CC2=C1
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INCHI for HMDB0034244 (Isoquinoline)

InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H7N
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
IUPAC Nameisoquinoline
Traditional Nameisoquinoline
CAS Registry Number119-65-3
SMILES
C1=CC=C2C=NC=CC2=C1
InChI Identifier
InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
InChI KeyAWJUIBRHMBBTKR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassNot Available
Direct ParentIsoquinolines and derivatives
Alternative Parents
Substituents
  • Isoquinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point25.5 - 26 °CNot Available
Boiling Point242.00 to 243.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.52 mg/mL at 25 °CNot Available
LogP2.08Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04329
Phenol Explorer Compound IDNot Available
FooDB IDFDB012557
KNApSAcK IDC00055955
Chemspider ID8098
KEGG Compound IDC06323
BioCyc IDISOQUINOLINE
BiGG IDNot Available
Wikipedia LinkIsoquinoline
METLIN IDNot Available
PubChem Compound8405
PDB IDISQ
ChEBI ID16092
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1034341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Candenas ML, Naline E, D'Ocon MP, Cortes D, Advenier C: Effects of cularine and other isoquinoline alkaloids on guinea-pig trachea and human bronchus. J Pharm Pharmacol. 1990 Feb;42(2):102-7. [PubMed:1972394 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .