NP-MRD: Showing NP-Card for (+)-Anomuricine (NP0083646)

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Record Information

Version

2.0

Created at

2022-04-29 04:37:13 UTC

Updated at

2022-04-29 04:37:13 UTC

NP-MRD ID

NP0083646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Anomuricine

Description

Xi-Anomuricine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Xi-Anomuricine is a very strong basic compound (based on its pKa). Outside of the human body, xi-Anomuricine has been detected, but not quantified in, fruits. (+)-Anomuricine is found in Annona muricata and Xylopia parviflora . This could make XI-anomuricine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    7.2502   -0.8542    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5130   -0.3799   -0.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1738   -0.0799   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917    0.3758   -1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422    0.6887   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    0.5519   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0281    0.8796    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362   -0.3056   -0.2184 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2773   -0.8721   -1.5081 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982   -0.1487   -2.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    0.8230   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031    0.5665   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945    0.0024   -0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -0.2386    1.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3169    0.0785    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089   -0.1590    2.4893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3008   -0.7414    3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187    0.6407    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695    0.9514    0.4240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3966    0.0311    0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3513    0.8865   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768    1.4548   -1.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345    0.0974    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950   -0.2257    1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629   -1.8940    0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -0.1749    1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3468   -0.8088    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230    0.4837   -2.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    1.0466   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    1.1855    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    1.6799   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -1.1192    0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -1.8925   -1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6425   -0.9120   -3.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6472    0.3106   -3.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    0.8487   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    1.8919   -2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -0.6812    1.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -0.0348    4.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7391   -1.6471    3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215   -1.1471    4.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0892    0.4170   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0159   -0.9601   -0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9904   -0.1021    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551    1.7020   -2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583   -0.0322    2.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429   -0.5847    1.8780 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 21  2  0
 21 22  1  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 14  1  0
 14 13  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 13  8  1  0
 13 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 22 45  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 14 38  1  0
 23 46  1  0
 24 47  1  0
M  END


  Mrv0541 05061310362D          

 24 26  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    2.1434   -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
    3.5724   -0.4125    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
    3.5724   -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
    2.8579   -2.4750    0.0000 O   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
    4.2868    0.0000    0.0000 O   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
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22  1  1  0  0  0  0
 22 13  1  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2NCCC3=C(O)C(OC)=C(OC)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-22-13-6-4-12(5-7-13)10-16-15-11-17(23-2)19(24-3)18(21)14(15)8-9-20-16/h4-7,11,16,20-21H,8-10H2,1-3H3

> <INCHI_KEY>
SQMUQBYKHDACDD-UHFFFAOYSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.3902

> <EXACT_MASS>
329.162708229

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.15615573028178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-5-ol

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.5886775767961536

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.132783087873802

> <JCHEM_PKA_STRONGEST_BASIC>
8.819880874205573

> <JCHEM_POLAR_SURFACE_AREA>
59.95

> <JCHEM_REFRACTIVITY>
93.0239

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    6   12                                                       
CONECT    5    7   12                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    9   14                                                       
CONECT    9    8   20                                                       
CONECT   10   12   16                                                       
CONECT   11   15   17                                                       
CONECT   12    4    5   10                                                  
CONECT   13    6    7   22                                                  
CONECT   14    8   15   18                                                  
CONECT   15   11   14   16                                                  
CONECT   16   10   15   20                                                  
CONECT   17   11   19   23                                                  
CONECT   18   14   19   21                                                  
CONECT   19   17   18   24                                                  
CONECT   20    9   16                                                       
CONECT   21   18                                                            
CONECT   22    1   13                                                       
CONECT   23    2   17                                                       
CONECT   24    3   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₄

Average Mass

329.3902 Da

Monoisotopic Mass

329.16271 Da

IUPAC Name

6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-5-ol

Traditional Name

6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-5-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2NCCC3=C(O)C(OC)=C(OC)C=C23)C=C1

InChI Identifier

InChI=1S/C19H23NO4/c1-22-13-6-4-12(5-7-13)10-16-15-11-17(23-2)19(24-3)18(21)14(15)8-9-20-16/h4-7,11,16,20-21H,8-10H2,1-3H3

InChI Key

SQMUQBYKHDACDD-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Annona muricata	Plant	KNApSAcK
Xylopia parviflora	Plant	KNApSAcK

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
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	2.37	ALOGPS
logP	2.59	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.95 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.02 m³·mol⁻¹	ChemAxon
Polarizability	36.16 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

HMDB0038724

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018132

KNApSAcK ID

Not Available

Chemspider ID

138360

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157209

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Anomuricine (NP0083646)

MOL for NP0083646 ((+)-Anomuricine)

3D MOL for NP0083646 ((+)-Anomuricine)

3D SDF for NP0083646 ((+)-Anomuricine)

3D-SDF for NP0083646 ((+)-Anomuricine)

PDB for NP0083646 ((+)-Anomuricine)

3D PDB for NP0083646 ((+)-Anomuricine)

SMILES for NP0083646 ((+)-Anomuricine)

INCHI for NP0083646 ((+)-Anomuricine)

Structure for NP0083646 ((+)-Anomuricine)

3D Structure for NP0083646 ((+)-Anomuricine)