NP-MRD: Showing NP-Card for nororientaline (NP0182515)

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Record Information

Version

2.0

Created at

2022-09-03 21:13:42 UTC

Updated at

2022-09-03 21:13:42 UTC

NP-MRD ID

NP0182515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nororientaline

Description

Nororientaline belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Nororientaline is a very strong basic compound (based on its pKa). nororientaline is found in Argemone platyceras and Erythrina variegata. An isoquinoline alkaloid consisting of aa tetrahydroisoquinoline core with 4-hydroxy-3-methoxybenzyl, methoxy and hydroxy substituents at positions 1, 6 and 7 respectively; major species at pH 7.3.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    4.8470    2.1394   -0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    0.8378   -0.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482   -0.1705   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148    0.0413   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571   -0.9529   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -0.5777   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0978   -0.1524    0.7576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1803   -1.1502    1.7471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584   -2.0653    1.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5957   -1.4988    1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668   -0.2699    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7439    0.2899    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261    1.4316   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9347    1.9659   -1.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1498    1.3139   -0.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5439    2.0722   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5985    3.2068   -1.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727    1.5331   -0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4012    0.3738    0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826   -2.2329    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8186   -2.4998    0.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7383   -1.4745    0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1012   -1.7394    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7425    2.7990   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3419    2.1772   -1.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    2.5392    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249    1.0762   -0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135    0.1819   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1427   -1.4778   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.7461    1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.8719    2.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -2.8251    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914   -2.6328    2.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795   -1.2581    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263   -2.2735    0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -0.2306    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2123    0.3287   -1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2391    1.0613    0.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9998    1.9520   -1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157    3.7557   -2.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    2.0392   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -3.0100    0.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -3.4991    0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7702   -0.9991    0.3943 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 19  7  1  0
 19 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 23 44  1  0
M  END


  Mrv1533004161519242D          

 23 25  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -0.4125    0.0000 C   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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    4.2868   -1.6500    0.0000 O   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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  7 19  1  0  0  0  0
 11 19  1  0  0  0  0
  5 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC2NCCC3=CC(OC)=C(O)C=C23)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-22-17-8-11(3-4-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3

> <INCHI_KEY>
WQTCGADWPORGNB-UHFFFAOYSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.369

> <EXACT_MASS>
315.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.23836809643552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.4890492132842166

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.48104704541184

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.88314791438989

> <JCHEM_PKA_STRONGEST_BASIC>
8.625296045548104

> <JCHEM_POLAR_SURFACE_AREA>
70.95

> <JCHEM_REFRACTIVITY>
88.54160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nororientaline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    7   11                                                  
CONECT   20    5   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₄

Average Mass

315.3690 Da

Monoisotopic Mass

315.14706 Da

IUPAC Name

1-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

nororientaline

CAS Registry Number

Not Available

SMILES

COC1=CC(CC2NCCC3=CC(OC)=C(O)C=C23)=CC=C1O

InChI Identifier

InChI=1S/C18H21NO4/c1-22-17-8-11(3-4-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3

InChI Key

WQTCGADWPORGNB-UHFFFAOYSA-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
Argemone platyceras	LOTUS Database	35616633
Erythrina variegata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:17048 )
isoquinolines (CHEBI:17048 )
isoquinolinol (CHEBI:17048 )

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	2.17	ALOGPS
logP	2.49	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	8.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.95 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.54 m³·mol⁻¹	ChemAxon
Polarizability	34.24 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

C05317

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440632

PDB ID

Not Available

ChEBI ID

17048

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for nororientaline (NP0182515)

MOL for NP0182515 (nororientaline)

3D MOL for NP0182515 (nororientaline)

3D SDF for NP0182515 (nororientaline)

3D-SDF for NP0182515 (nororientaline)

PDB for NP0182515 (nororientaline)

3D PDB for NP0182515 (nororientaline)

SMILES for NP0182515 (nororientaline)

INCHI for NP0182515 (nororientaline)

Structure for NP0182515 (nororientaline)

3D Structure for NP0182515 (nororientaline)