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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:18:25 UTC

Update Date

2021-09-26 22:51:38 UTC

HMDB ID

HMDB0244117

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Description

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, also known as tic-aa, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Based on a literature review a significant number of articles have been published on 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1652309102123182D          

 13 14  0  0  0  0            999 V2000
    1.4289   -1.6500    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   -0.4125    0.0000 N   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
    2.1434   -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
    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
    2.8579   -1.6500    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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244117

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1CC2=CC=CC=C2CN1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)

> <INCHI_KEY>
BWKMGYQJPOAASG-UHFFFAOYSA-N

> <FORMULA>
C10H11NO2

> <MOLECULAR_WEIGHT>
177.203

> <EXACT_MASS>
177.078978598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.51208919717648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-1.2084335922204583

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8478828840154673

> <JCHEM_PKA_STRONGEST_BASIC>
9.070531070044728

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
48.4455

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5    1                                                  
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydroisoquinoline-3-carboxylate	Generator
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, (+-)-isomer	HMDB
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, (S)-isomer	HMDB
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, hydrochloride	HMDB
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, hydrochloride, (S)-isomer	HMDB
Tic-aa	HMDB
Tetrahydro-3-isoquinoline carboxylic acid	HMDB

Chemical Formula

C₁₀H₁₁NO₂

Average Molecular Weight

177.203

Monoisotopic Molecular Weight

177.078978598

IUPAC Name

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Traditional Name

1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1CC2=CC=CC=C2CN1

InChI Identifier

InChI=1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)

InChI Key

BWKMGYQJPOAASG-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

Alpha-amino acid
Alpha-amino acid or derivatives
Tetrahydroisoquinoline
Aralkylamine
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Azacycle
Secondary amine
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-1.6	ALOGPS
logP	-1.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	18.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	129.791	30932474
DeepCCS	[M-H]-	126.058	30932474
DeepCCS	[M-2H]-	163.439	30932474
DeepCCS	[M+Na]+	138.978	30932474
AllCCS	[M+H]+	140.7	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.6	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	139.0	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	140.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid	OC(=O)C1CC2=CC=CC=C2CN1	2748.9	Standard polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid	OC(=O)C1CC2=CC=CC=C2CN1	1611.1	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid	OC(=O)C1CC2=CC=CC=C2CN1	1766.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C	1811.6	Semi standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C	1790.5	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C	2087.3	Standard polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C(C)(C)C	2266.0	Semi standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C(C)(C)C	2282.2	Standard non polar	33892256
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC2=CC=CC=C2CN1[Si](C)(C)C(C)(C)C	2376.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0900000000-bea56edf248b5eb4cc15	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 10V, Positive-QTOF	splash10-003r-0900000000-5dc9a9ea1995940aecf4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 20V, Positive-QTOF	splash10-001i-1900000000-eb11c6693bbb77029e75	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 40V, Positive-QTOF	splash10-0k96-5900000000-02404261486fe1976278	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 10V, Negative-QTOF	splash10-004i-0900000000-66736afa726a9ce244a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 20V, Negative-QTOF	splash10-001i-0900000000-e9f931c8ba23cc1d8339	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 40V, Negative-QTOF	splash10-001i-1900000000-934b4302e88e18a9c637	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

86184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95489

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (HMDB0244117)

MOL for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

3D MOL for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

3D SDF for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

3D-SDF for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

PDB for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

3D PDB for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

SMILES for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

INCHI for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

Structure for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

3D Structure for HMDB0244117 (1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra