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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:35 UTC

Update Date

2023-02-21 17:17:50 UTC

HMDB ID

HMDB0012490

Secondary Accession Numbers

HMDB12490

Metabolite Identification

Common Name

1,2-Dehydrosalsolinol

Description

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. Liquid chromatographic analysis of incubations for varying times (30 min to 5 h) showed that the tetrahydroisoquinoline substrate decarboxylated oxidatively, forming the DSAL (PMID: 3369867 ). It is involved in Tyrosine Metabolism.

Structure

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


  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>
HMDB0012490

> <DATABASE_NAME>
hmdb

> <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

$$$$

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-6,7-dihydroxy-3,4-dihydroisoquinolines	HMDB
3,4-dihydro-1-Methyl-6,7-isoquinolinediol	HMDB
DSAL	HMDB

Chemical Formula

C₁₀H₁₁NO₂

Average Molecular Weight

177.1998

Monoisotopic Molecular Weight

177.078978601

IUPAC Name

1-methyl-3,4-dihydroisoquinoline-6,7-diol

Traditional Name

1-methyl-3,4-dihydroisoquinoline-6,7-diol

CAS Registry Number

4602-81-7

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

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydroisoquinolines

Sub Class

Not Available

Direct Parent

Dihydroisoquinolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0012490)

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	0.78 g/L	ALOGPS
logP	1.19	ALOGPS
logP	1.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	5.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.69 m³·mol⁻¹	ChemAxon
Polarizability	18.65 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]+	141.798	31661259
DarkChem	[M-H]-	138.477	31661259
DeepCCS	[M+H]+	139.454	30932474
DeepCCS	[M-H]-	135.626	30932474
DeepCCS	[M-2H]-	173.062	30932474
DeepCCS	[M+Na]+	148.6	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.0	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	139.1	32859911
AllCCS	[M+HCOO]-	139.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	2.17 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1493 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	131.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	775.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	39.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	274.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	259.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	491.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	613.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	189.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	736.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	206.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	478.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	381.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	173.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dehydrosalsolinol	CC1=NCCC2=C1C=C(O)C(O)=C2	2684.2	Standard polar	33892256
1,2-Dehydrosalsolinol	CC1=NCCC2=C1C=C(O)C(O)=C2	1754.5	Standard non polar	33892256
1,2-Dehydrosalsolinol	CC1=NCCC2=C1C=C(O)C(O)=C2	1916.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dehydrosalsolinol,1TMS,isomer #1	CC1=NCCC2=CC(O)=C(O[Si](C)(C)C)C=C12	1824.9	Semi standard non polar	33892256
1,2-Dehydrosalsolinol,1TMS,isomer #2	CC1=NCCC2=CC(O[Si](C)(C)C)=C(O)C=C12	1851.6	Semi standard non polar	33892256
1,2-Dehydrosalsolinol,2TMS,isomer #1	CC1=NCCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C12	1863.5	Semi standard non polar	33892256
1,2-Dehydrosalsolinol,1TBDMS,isomer #1	CC1=NCCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C12	2103.6	Semi standard non polar	33892256
1,2-Dehydrosalsolinol,1TBDMS,isomer #2	CC1=NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C12	2111.1	Semi standard non polar	33892256
1,2-Dehydrosalsolinol,2TBDMS,isomer #1	CC1=NCCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C12	2328.3	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 - 1,2-Dehydrosalsolinol GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-1392000000-f1e4a0be2f7e97323ee6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dehydrosalsolinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0900000000-12d9d22ce9d1f53763a2	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dehydrosalsolinol 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 - 1,2-Dehydrosalsolinol 10V, Positive-QTOF	splash10-004i-0900000000-3353063db7785c56ab4b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Positive-QTOF	splash10-002r-1900000000-60a5f8487936dabfac02	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Positive-QTOF	splash10-00vr-7900000000-9a57ee165717efdad1c8	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Negative-QTOF	splash10-004i-0900000000-f972bf5f261cc77d06c0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Negative-QTOF	splash10-004i-0900000000-7529c280110b6380588a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Negative-QTOF	splash10-07w9-1900000000-3d8656d3388a0f99e63e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Negative-QTOF	splash10-004i-0900000000-ef6ae59e91e658cf298a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Negative-QTOF	splash10-004i-0900000000-ce3e229270093bb2c74b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Negative-QTOF	splash10-00xr-1900000000-f91c36aaafb986741bf5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 10V, Positive-QTOF	splash10-004i-0900000000-287b3d60ee7ac7576fb4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 20V, Positive-QTOF	splash10-004i-0900000000-5def6855fd9d71e1370e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dehydrosalsolinol 40V, Positive-QTOF	splash10-0a4i-4900000000-e69f269d4d26d100a113	2021-09-25	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

FDB029097

KNApSAcK ID

Not Available

Chemspider ID

17960720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20844

PDB ID

Not Available

ChEBI ID

193796

Food Biomarker Ontology

Not Available

VMH ID

CE5629

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:3369867 ]

Showing metabocard for 1,2-Dehydrosalsolinol (HMDB0012490)

MOL for HMDB0012490 (1,2-Dehydrosalsolinol)

3D MOL for HMDB0012490 (1,2-Dehydrosalsolinol)

3D SDF for HMDB0012490 (1,2-Dehydrosalsolinol)

3D-SDF for HMDB0012490 (1,2-Dehydrosalsolinol)

PDB for HMDB0012490 (1,2-Dehydrosalsolinol)

3D PDB for HMDB0012490 (1,2-Dehydrosalsolinol)

SMILES for HMDB0012490 (1,2-Dehydrosalsolinol)

INCHI for HMDB0012490 (1,2-Dehydrosalsolinol)

Structure for HMDB0012490 (1,2-Dehydrosalsolinol)

3D Structure for HMDB0012490 (1,2-Dehydrosalsolinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra