NP-MRD: Showing NP-Card for methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (NP0304112)

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Record Information

Version

2.0

Created at

2022-09-10 18:57:54 UTC

Updated at

2022-09-10 18:57:54 UTC

NP-MRD ID

NP0304112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Description

(3S)-8-Bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate is found in Rhodomela confervoides. Based on a literature review very few articles have been published on (3S)-8-Bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -5.4406    0.8222   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286    0.4163    0.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562   -0.3835   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8266   -0.7924   -1.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -0.7571   -0.1917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2148    0.4827    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    0.2714    0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002    1.3642    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4632    1.1910    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558    2.2430    0.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9656   -0.0515   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -0.2566   -0.1772 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1168   -0.6278    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -1.1225   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191   -2.8671   -0.7106 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7600   -0.9796   -0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -2.1463   -0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -1.5912   -1.1576 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5517    1.8586    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6961    0.7914   -1.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088    0.2152    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002   -1.3899    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386    0.7498    1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776    1.3592   -0.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    2.3382    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9880    3.1730    0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790   -0.0747    1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0306   -1.7193    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1834   -0.3892    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294   -2.9379   -1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188   -2.4609    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9334   -1.0598   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  5  1  0
 16  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  1
  6 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv1652309102220572D          

 18 19  0  0  1  0            999 V2000
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    4.2868   -0.0000    0.0000 O   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
    4.2868   -1.6500    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 Br  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
    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 N   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  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  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  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1CC2=CC(O)=C(OC)C(Br)=C2CN1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14BrNO4/c1-17-11-9(15)4-6-3-8(12(16)18-2)14-5-7(6)10(11)13/h4,8,14-15H,3,5H2,1-2H3/t8-/m0/s1

> <INCHI_KEY>
OAYVVDQWZFAYNG-QMMMGPOBSA-N

> <FORMULA>
C12H14BrNO4

> <MOLECULAR_WEIGHT>
316.151

> <EXACT_MASS>
315.010621

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.021134524613807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3S)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

> <JCHEM_LOGP>
1.7148328419999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.223139971375259

> <JCHEM_PKA_STRONGEST_BASIC>
4.1704905937546215

> <JCHEM_POLAR_SURFACE_AREA>
67.79

> <JCHEM_REFRACTIVITY>
69.28150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       5.335  -4.620   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    5                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(3S)-8-Bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate methyl ester	Generator

Chemical Formula

C₁₂H₁₄BrNO₄

Average Mass

316.1510 Da

Monoisotopic Mass

315.01062 Da

IUPAC Name

methyl (3S)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Traditional Name

methyl (3S)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1CC2=CC(O)=C(OC)C(Br)=C2CN1

InChI Identifier

InChI=1S/C12H14BrNO4/c1-17-11-9(15)4-6-3-8(12(16)18-2)14-5-7(6)10(11)13/h4,8,14-15H,3,5H2,1-2H3/t8-/m0/s1

InChI Key

OAYVVDQWZFAYNG-QMMMGPOBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhodomela confervoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Tetrahydroisoquinoline
Anisole
3-halophenol
Phenol ether
3-bromophenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Aryl bromide
Aryl halide
Benzenoid
Methyl ester
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Secondary aliphatic amine
Ether
Secondary amine
Monocarboxylic acid or derivatives
Organic oxide
Amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organohalogen compound
Organobromide
Organonitrogen compound
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	1.71	ChemAxon
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	4.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.28 m³·mol⁻¹	ChemAxon
Polarizability	28.02 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17214478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16115982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (NP0304112)

MOL for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

3D MOL for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

3D SDF for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

3D-SDF for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

PDB for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

3D PDB for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

SMILES for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

INCHI for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

Structure for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)

3D Structure for NP0304112 (methyl (3s)-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate)