NP-MRD: Showing NP-Card for betagarin (NP0246217)

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Record Information

Version

2.0

Created at

2022-09-07 07:36:19 UTC

Updated at

2022-09-07 07:36:19 UTC

NP-MRD ID

NP0246217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

betagarin

Description

Betagarin belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Thus, betagarin is considered to be a flavonoid lipid molecule. Betagarin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. betagarin is found in Beta vulgaris. An extended flavonoid that is 6,7-methylenedioxyflavanone substituted by methoxy groups at positions 5 and 2' respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -4.0342   -0.9767   -2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0874   -0.4616   -1.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0984    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583   -0.2247    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534    0.1612    1.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9329    0.6745    2.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    0.8285    2.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    0.4392    0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037    0.4781    0.3009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5566    1.6203   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.6279   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5797    2.6685   -0.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6729    0.4369   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994   -0.7500    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -1.9260    0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0438   -1.8794    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7359   -0.7225    0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413    0.4156   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260    1.6345   -0.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138    1.7856   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101   -0.9190    0.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2095   -2.1211    1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026   -2.8273    0.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -0.7221   -0.0752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -1.6203   -2.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658   -1.5641   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5665   -0.1419   -2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4571   -0.6483   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9873    0.0280    2.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962    1.0058    3.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764    1.2415    2.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974    0.7795    1.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299    1.3437   -1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9550    2.5997   -0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1035   -2.8375    0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1833    1.5037   -1.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165    1.0503   -2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9442    2.7672   -2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -1.9094    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0518   -2.7399    0.8426 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 18  2  0
 18 19  1  0
 19 20  1  0
 18 17  1  0
 17 16  2  0
 16 23  1  0
 23 22  1  0
 22 21  1  0
 16 15  1  0
 15 14  2  0
 14 24  1  0
  8  3  1  0
 24  9  1  0
 14 13  1  0
 21 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
 15 35  1  0
M  END

Betagarin
  Mrv1572001071604372D          

 24 27  0  0  1  0            999 V2000
    4.7168    0.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -0.7344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697    0.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -1.7204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7072   -1.7490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8964   -0.4602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4643    0.3593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4643   -0.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793   -0.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7168   -0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1771    0.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648   -0.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -0.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8932    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1740    1.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2882   -0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6061    0.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8869    2.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6029    1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -2.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  1 10  1  0  0  0  0
  2 14  1  0  0  0  0
  2 19  1  0  0  0  0
  3 16  1  0  0  0  0
  3 19  1  0  0  0  0
  4 13  1  0  0  0  0
  5 11  2  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  6  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 15  2  0  0  0  0
 12 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 14  1  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
  4 23  1  0  0  0  0
  6 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1[C@@H]1CC(=O)C2=C(OC)C3=C(OCO3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-20-12-6-4-3-5-10(12)13-7-11(19)16-14(24-13)8-15-17(18(16)21-2)23-9-22-15/h3-6,8,13H,7,9H2,1-2H3/t13-/m0/s1

> <INCHI_KEY>
IHPVFYLOGNNZLA-ZDUSSCGKSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.626014108035925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11S)-2-methoxy-11-(2-methoxyphenyl)-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.403694951666666

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.55694043329817

> <JCHEM_PKA_STRONGEST_BASIC>
-4.276820265951191

> <JCHEM_POLAR_SURFACE_AREA>
63.22

> <JCHEM_REFRACTIVITY>
84.0404

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
betagarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Betagarin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0       8.805   1.462   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.303  -1.371   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.303   1.108   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.094  -3.211   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.787  -3.265   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.873  -0.859   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.200   0.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.200  -0.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.428  -0.901   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.428   0.639   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.805  -1.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.531   1.446   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.094  -1.671   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.761  -0.901   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.094   1.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.761   0.639   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.867   0.681   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.525   2.986   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.405  -0.131   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.198   1.456   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.856   3.761   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.192   2.996   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.761  -3.981   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.210  -1.624   0.000  0.00  0.00           C+0
CONECT    1    7   10                                                       
CONECT    2   14   19                                                       
CONECT    3   16   19                                                       
CONECT    4   13   23                                                       
CONECT    5   11                                                            
CONECT    6   17   24                                                       
CONECT    7    1    8   12                                                  
CONECT    8    7   11                                                       
CONECT    9   10   11   13                                                  
CONECT   10    1    9   15                                                  
CONECT   11    5    8    9                                                  
CONECT   12    7   17   18                                                  
CONECT   13    4    9   14                                                  
CONECT   14    2   13   16                                                  
CONECT   15   10   16                                                       
CONECT   16    3   14   15                                                  
CONECT   17    6   12   20                                                  
CONECT   18   12   21                                                       
CONECT   19    2    3                                                       
CONECT   20   17   22                                                       
CONECT   21   18   22                                                       
CONECT   22   20   21                                                       
CONECT   23    4                                                            
CONECT   24    6                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
5,2'-Dimethoxy-6,7-methylenedioxyflavanone	ChEBI

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(11S)-2-methoxy-11-(2-methoxyphenyl)-4,6,10-trioxatricyclo[7.4.0.0³,⁷]trideca-1,3(7),8-trien-13-one

Traditional Name

betagarin

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1[C@@H]1CC(=O)C2=C(OC)C3=C(OCO3)C=C2O1

InChI Identifier

InChI=1S/C18H16O6/c1-20-12-6-4-3-5-10(12)13-7-11(19)16-14(24-13)8-15-17(18(16)21-2)23-9-22-15/h3-6,8,13H,7,9H2,1-2H3/t13-/m0/s1

InChI Key

IHPVFYLOGNNZLA-ZDUSSCGKSA-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
Beta vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

2p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
Flavanone
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Aryl ketone
Phenol ether
Aryl alkyl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ketone
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:27679 )
dimethoxyflavanone (CHEBI:27679 )
extended flavonoid (CHEBI:27679 )
flavanones (C09479 )
Flavanones (LMPK12140599 )

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	2.2	ALOGPS
logP	2.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.04 m³·mol⁻¹	ChemAxon
Polarizability	33.63 Å³	ChemAxon
Number of Rings	4	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

C00000942

Chemspider ID

Not Available

KEGG Compound ID

C09479

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442261

PDB ID

Not Available

ChEBI ID

27679

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for betagarin (NP0246217)

MOL for NP0246217 (betagarin)

3D MOL for NP0246217 (betagarin)

3D SDF for NP0246217 (betagarin)

3D-SDF for NP0246217 (betagarin)

PDB for NP0246217 (betagarin)

3D PDB for NP0246217 (betagarin)

SMILES for NP0246217 (betagarin)

INCHI for NP0246217 (betagarin)

Structure for NP0246217 (betagarin)

3D Structure for NP0246217 (betagarin)