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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:12:53 UTC

Update Date

2022-03-07 02:57:03 UTC

HMDB ID

HMDB0041526

Secondary Accession Numbers

HMDB41526

Metabolite Identification

Common Name

Isosalsolidine

Description

Isosalsolidine 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. Isosalsolidine has been detected, but not quantified in, herbs and spices. This could make isosalsolidine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isosalsolidine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061312442D          

 15 16  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041526

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C(C)=NC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO2/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8/h4-7H,1-3H3

> <INCHI_KEY>
VBMZFACBWDZUSM-UHFFFAOYSA-N

> <FORMULA>
C12H13NO2

> <MOLECULAR_WEIGHT>
203.2371

> <EXACT_MASS>
203.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.95206733366661

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dimethoxy-1-methylisoquinoline

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.561077783333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.946918160086281

> <JCHEM_POLAR_SURFACE_AREA>
31.35

> <JCHEM_REFRACTIVITY>
57.869200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dimethoxy-1-methylisoquinoline

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   13                                                       
CONECT    6    9   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1   10   13                                                  
CONECT    9    4    6   10                                                  
CONECT   10    7    8    9                                                  
CONECT   11    6   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    5    8                                                       
CONECT   14    2   11                                                       
CONECT   15    3   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0041526
HETATM    1  C1  UNL     1       3.230  -2.403  -0.274  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.897  -1.034  -0.250  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.574  -0.639  -0.134  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.580  -1.587  -0.042  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.735  -1.215   0.074  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.733  -2.192   0.167  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.051  -1.801   0.283  1.00  0.00           C  
HETATM    8  N1  UNL     1      -3.382  -0.483   0.306  1.00  0.00           N  
HETATM    9  C7  UNL     1      -2.441   0.474   0.219  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.758   1.925   0.241  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.114   0.111   0.102  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.118   1.074   0.009  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.198   0.683  -0.106  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.182   1.634  -0.198  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.847   2.996  -0.174  1.00  0.00           C  
HETATM   16  H1  UNL     1       2.728  -2.980   0.531  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.322  -2.490  -0.115  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.997  -2.795  -1.285  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.778  -2.650  -0.055  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.474  -3.253   0.148  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.829  -2.551   0.355  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.168   2.452   1.038  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.846   2.086   0.473  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.587   2.380  -0.757  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.390   2.139   0.029  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.465   3.357   0.786  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.754   3.590  -0.424  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.073   3.171  -0.949  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   19
CONECT    5    6    6   11
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9
CONECT    9   10   11   11
CONECT   10   22   23   24
CONECT   11   12
CONECT   12   13   13   25
CONECT   13   14
CONECT   14   15
CONECT   15   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-Dimethoxy-1-methylisoquinoline, 9ci	HMDB
Nigellimine	HMDB

Chemical Formula

C₁₂H₁₃NO₂

Average Molecular Weight

203.2371

Monoisotopic Molecular Weight

203.094628665

IUPAC Name

6,7-dimethoxy-1-methylisoquinoline

Traditional Name

6,7-dimethoxy-1-methylisoquinoline

CAS Registry Number

4594-02-9

SMILES

COC1=C(OC)C=C2C(C)=NC=CC2=C1

InChI Identifier

InChI=1S/C12H13NO2/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8/h4-7H,1-3H3

InChI Key

VBMZFACBWDZUSM-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Not Available

Direct Parent

Isoquinolines and derivatives

Alternative Parents

Substituents

Isoquinoline
Anisole
Alkyl aryl ether
Methylpyridine
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041526)
Cell membrane (HMDB: HMDB0041526)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041526)

Source

Exogenous

Exogenous (HMDB: HMDB0041526)

Food

Food (HMDB: HMDB0041526)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041526)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041526)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 119 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	427 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.49 g/L	ALOGPS
logP	2.55	ALOGPS
logP	1.56	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	6.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	31.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.87 m³·mol⁻¹	ChemAxon
Polarizability	21.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.121	31661259
DarkChem	[M-H]-	145.257	31661259
DeepCCS	[M+H]+	147.645	30932474
DeepCCS	[M-H]-	145.287	30932474
DeepCCS	[M-2H]-	179.151	30932474
DeepCCS	[M+Na]+	154.001	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	139.6	32859911
AllCCS	[M+NH4]+	147.8	32859911
AllCCS	[M+Na]+	149.0	32859911
AllCCS	[M-H]-	147.9	32859911
AllCCS	[M+Na-2H]-	148.1	32859911
AllCCS	[M+HCOO]-	148.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isosalsolidine	COC1=C(OC)C=C2C(C)=NC=CC2=C1	2499.8	Standard polar	33892256
Isosalsolidine	COC1=C(OC)C=C2C(C)=NC=CC2=C1	1748.2	Standard non polar	33892256
Isosalsolidine	COC1=C(OC)C=C2C(C)=NC=CC2=C1	1907.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isosalsolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lya-0910000000-f3d54cce6057f06711eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosalsolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isosalsolidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 10V, Positive-QTOF	splash10-0udi-0190000000-78ab735f37f6f568088c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 20V, Positive-QTOF	splash10-0udi-0390000000-96a856c44c481e809566	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 40V, Positive-QTOF	splash10-07br-0900000000-b62afa6b5c16922001fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 10V, Negative-QTOF	splash10-0udi-0090000000-c2b020c916ea96b67c98	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 20V, Negative-QTOF	splash10-0udi-0190000000-5e6dc8c0f4f8efbad400	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 40V, Negative-QTOF	splash10-05rs-0900000000-3999a7b95ddde4e5d9f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 10V, Negative-QTOF	splash10-0udi-0090000000-341f1e0a28e483a04bd3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 20V, Negative-QTOF	splash10-0udi-0190000000-1dd19b3df6dad06a42fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 40V, Negative-QTOF	splash10-00kf-0900000000-d5582398a689a4d55f72	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 10V, Positive-QTOF	splash10-0udi-0090000000-b81b75e675178531e9bb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 20V, Positive-QTOF	splash10-0udi-0090000000-c078991821010bee4813	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isosalsolidine 40V, Positive-QTOF	splash10-03l0-0900000000-289a3c1080455975ddf0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021503

KNApSAcK ID

C00028688

Chemspider ID

19514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20725

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1893111

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isosalsolidine (HMDB0041526)

MOL for HMDB0041526 (Isosalsolidine)

3D MOL for HMDB0041526 (Isosalsolidine)

3D SDF for HMDB0041526 (Isosalsolidine)

3D-SDF for HMDB0041526 (Isosalsolidine)

PDB for HMDB0041526 (Isosalsolidine)

3D PDB for HMDB0041526 (Isosalsolidine)

SMILES for HMDB0041526 (Isosalsolidine)

INCHI for HMDB0041526 (Isosalsolidine)

Structure for HMDB0041526 (Isosalsolidine)

3D Structure for HMDB0041526 (Isosalsolidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra