NP-MRD: Showing NP-Card for Salsolinol-1-carboxylate (NP0339178)

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Record Information

Version

2.0

Created at

2024-09-11 20:09:34 UTC

Updated at

2024-09-11 20:09:35 UTC

NP-MRD ID

NP0339178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Salsolinol-1-carboxylate

Description

Salsolinol 1-carboxylate, also known as SAL-1C, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Salsolinol 1-carboxylate is a very strong basic compound (based on its pKa). Salsolinol 1-carboxylate is an intermediate metabolite formed during the synthesis with dopamine and pyruvate towards the endogenous neurotoxin, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (salsolinol),which has been considered a potential causative factor for Parkinsons disease (PD).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016492D          

 16 17  0  0  1  0            999 V2000
   11.8725  -13.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4600  -13.9607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7454  -14.3732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7454  -15.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4600  -15.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1745  -15.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8891  -15.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6030  -15.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3176  -15.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6030  -14.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3176  -13.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8891  -13.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1745  -14.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0474  -13.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4600  -12.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2225  -13.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 13  1  0  0  0  0
  2 14  1  6  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(NCCC2=C1C=C(O)C(O)=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO4/c1-11(10(15)16)7-5-9(14)8(13)4-6(7)2-3-12-11/h4-5,12-14H,2-3H2,1H3,(H,15,16)/t11-/m0/s1

> <INCHI_KEY>
XHGLVMDBZZZXDP-NSHDSACASA-N

> <FORMULA>
C11H13NO4

> <MOLECULAR_WEIGHT>
223.2252

> <EXACT_MASS>
223.084457909

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.046376231448832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

> <ALOGPS_LOGP>
-0.15

> <JCHEM_LOGP>
-1.383656223558682

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.517872134193771

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1368066541894475

> <JCHEM_PKA_STRONGEST_BASIC>
8.563462462356483

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
57.1206

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-6,7-dihydroxy-1-methyl-3,4-dihydro-2H-isoquinoline-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      22.162 -24.726   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.392 -26.060   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      20.058 -26.830   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      20.058 -28.370   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.392 -29.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.726 -28.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.060 -29.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.392 -28.370   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      26.726 -29.140   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      25.392 -26.830   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      26.726 -26.060   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.060 -26.060   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.726 -26.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.622 -24.726   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.392 -23.392   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      19.082 -24.726   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13   14                                             
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                                                  
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Salsolinol 1-carboxylic acid	Generator
1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid	HMDB
SAL-1C	HMDB
Salsolinol-1-carboxylic acid	HMDB
(1S)-6,7-Dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate	Generator

Chemical Formula

C₁₁H₁₃NO₄

Average Mass

223.2252 Da

Monoisotopic Mass

223.08446 Da

IUPAC Name

(1S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Traditional Name

(1S)-6,7-dihydroxy-1-methyl-3,4-dihydro-2H-isoquinoline-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]1(NCCC2=C1C=C(O)C(O)=C2)C(O)=O

InChI Identifier

InChI=1S/C11H13NO4/c1-11(10(15)16)7-5-9(14)8(13)4-6(7)2-3-12-11/h4-5,12-14H,2-3H2,1H3,(H,15,16)/t11-/m0/s1

InChI Key

XHGLVMDBZZZXDP-NSHDSACASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxylic acid salt
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic zwitterion
Carbonyl group
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.15	ALOGPS
logP	-1.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.14	ChemAxon
pKa (Strongest Basic)	8.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.12 m³·mol⁻¹	ChemAxon
Polarizability	22.05 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

External Links

HMDB ID

HMDB0013068

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029280

KNApSAcK ID

Not Available

Chemspider ID

5412232

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7055179

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Salsolinol-1-carboxylate (NP0339178)

MOL for NP0339178 (Salsolinol-1-carboxylate)

3D MOL for NP0339178 (Salsolinol-1-carboxylate)

3D SDF for NP0339178 (Salsolinol-1-carboxylate)

3D-SDF for NP0339178 (Salsolinol-1-carboxylate)

PDB for NP0339178 (Salsolinol-1-carboxylate)

3D PDB for NP0339178 (Salsolinol-1-carboxylate)

SMILES for NP0339178 (Salsolinol-1-carboxylate)

INCHI for NP0339178 (Salsolinol-1-carboxylate)

Structure for NP0339178 (Salsolinol-1-carboxylate)

3D Structure for NP0339178 (Salsolinol-1-carboxylate)