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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 21:04:35 UTC

Update Date

2023-02-21 17:17:14 UTC

HMDB ID

HMDB0006044

Secondary Accession Numbers

HMDB06044

Metabolite Identification

Common Name

Norsalsolinol

Description

Norsalsolinol is a putative metabolic neuromodulators that hs been found to be present in both rat and human brains. It modulates dopaminergic transmission and have been shown to be associated with neurotoxicity within cells and diseases such as alcoholism and Parkinsonism. Norsalsolinol can be synthesized in vivo non-enzymatically by condensation of dopamine with formaldehyde, the oxidized metabolite of methanol.

Structure

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

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  O   UNK     0      21.861 -26.910   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      23.195 -26.140   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.528 -26.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.862 -26.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.196 -26.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.528 -26.140   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      28.528 -24.600   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      27.196 -23.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.862 -24.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.528 -23.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.195 -24.600   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      21.861 -23.830   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Norsalsolinol hydrobromide	MeSH
Norsalsolinol hydrochloride	MeSH
Norsalsolinol, 3H-labeled CPD	MeSH
1,2,3,4-tetrahydro-6,7-Isoquinolinediol	HMDB
6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline	HMDB
6,7-Dihydroxytetrahydroisoquinoline	HMDB
tetrahydro-6,7-Isoquinolinediol	HMDB
Norsalsolinol	MeSH

Chemical Formula

C₉H₁₁NO₂

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

IUPAC Name

1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

norsalsolinol

CAS Registry Number

34827-33-3

SMILES

OC1=C(O)C=C2CNCCC2=C1

InChI Identifier

InChI=1S/C9H11NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-4,10-12H,1-2,5H2

InChI Key

MBFUSGLXKQWVDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0006044)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.58	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.58 m³·mol⁻¹	ChemAxon
Polarizability	17.28 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.404	31661259
DarkChem	[M-H]-	130.224	31661259
DeepCCS	[M+H]+	137.746	30932474
DeepCCS	[M-H]-	134.448	30932474
DeepCCS	[M-2H]-	171.414	30932474
DeepCCS	[M+Na]+	146.952	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	135.3	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norsalsolinol	OC1=C(O)C=C2CNCCC2=C1	2368.2	Standard polar	33892256
Norsalsolinol	OC1=C(O)C=C2CNCCC2=C1	1770.2	Standard non polar	33892256
Norsalsolinol	OC1=C(O)C=C2CNCCC2=C1	1886.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norsalsolinol,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O)CNCC2	1832.8	Semi standard non polar	33892256
Norsalsolinol,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2	1832.9	Semi standard non polar	33892256
Norsalsolinol,1TMS,isomer #3	C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1	1973.5	Semi standard non polar	33892256
Norsalsolinol,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CNCC2	1866.0	Semi standard non polar	33892256
Norsalsolinol,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)CN([Si](C)(C)C)CC2	1886.7	Semi standard non polar	33892256
Norsalsolinol,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)C2	1874.7	Semi standard non polar	33892256
Norsalsolinol,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC2	1932.9	Semi standard non polar	33892256
Norsalsolinol,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC2	1967.8	Standard non polar	33892256
Norsalsolinol,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)CN([Si](C)(C)C)CC2	2062.4	Standard polar	33892256
Norsalsolinol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CNCC2	2114.0	Semi standard non polar	33892256
Norsalsolinol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2	2107.6	Semi standard non polar	33892256
Norsalsolinol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1	2178.6	Semi standard non polar	33892256
Norsalsolinol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CNCC2	2347.8	Semi standard non polar	33892256
Norsalsolinol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CN([Si](C)(C)C(C)(C)C)CC2	2371.9	Semi standard non polar	33892256
Norsalsolinol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)C2	2373.2	Semi standard non polar	33892256
Norsalsolinol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC2	2630.0	Semi standard non polar	33892256
Norsalsolinol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC2	2657.5	Standard non polar	33892256
Norsalsolinol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CN([Si](C)(C)C(C)(C)C)CC2	2465.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norsalsolinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01bi-1900000000-679885412288d3a64d3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norsalsolinol GC-MS (2 TMS) - 70eV, Positive	splash10-00du-3190000000-6081caf19417015960d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norsalsolinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norsalsolinol 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 - Norsalsolinol 10V, Positive-QTOF	splash10-014i-0900000000-6a97378ae1f9b27d97f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 20V, Positive-QTOF	splash10-014r-0900000000-2e841407c0716ade36d1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 40V, Positive-QTOF	splash10-106v-7900000000-825205ecfbbbc20670c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 10V, Negative-QTOF	splash10-03di-0900000000-9ebff04bba1dd29e170f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 20V, Negative-QTOF	splash10-03di-0900000000-c11ff999c02984e87d5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 40V, Negative-QTOF	splash10-0a4m-4900000000-e08e2858281b324fde48	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 10V, Negative-QTOF	splash10-03di-0900000000-58730e09c186a15c21ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 20V, Negative-QTOF	splash10-03di-0900000000-08447749b14e173ff102	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 40V, Negative-QTOF	splash10-0006-9700000000-5d6e4fb1e2ebc89ffec3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 10V, Positive-QTOF	splash10-014i-0900000000-ec6dcf9afb4af34cdf10	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 20V, Positive-QTOF	splash10-014i-0900000000-6e01e6a1fb7a92704dd8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norsalsolinol 40V, Positive-QTOF	splash10-00kf-9600000000-8c87667ad0decf4c3747	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB023817

KNApSAcK ID

Not Available

Chemspider ID

33891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norsalsolinol

METLIN ID

Not Available

PubChem Compound

36937

PDB ID

Not Available

ChEBI ID

110006

Food Biomarker Ontology

Not Available

VMH ID

CE2172

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Norsalsolinol (HMDB0006044)

MOL for HMDB0006044 (Norsalsolinol)

3D MOL for HMDB0006044 (Norsalsolinol)

3D SDF for HMDB0006044 (Norsalsolinol)

3D-SDF for HMDB0006044 (Norsalsolinol)

PDB for HMDB0006044 (Norsalsolinol)

3D PDB for HMDB0006044 (Norsalsolinol)

SMILES for HMDB0006044 (Norsalsolinol)

INCHI for HMDB0006044 (Norsalsolinol)

Structure for HMDB0006044 (Norsalsolinol)

3D Structure for HMDB0006044 (Norsalsolinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra