NP-MRD: Showing NP-Card for Betanin (NP0045360)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:36 UTC

Updated at

2022-03-17 19:18:36 UTC

NP-MRD ID

NP0045360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betanin

Description

Gamma-Ionone, also known as g-ionon or fema 3175, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Gamma-Ionone is an extremely weak basic (essentially neutral) compound (based on its pKa). Gamma-Ionone is a floral and woody tasting compound. Outside of the human body, gamma-Ionone has been detected, but not quantified in, tamarinds. Betanin is found in Amaranthus caudatus, Amaranthus mangostanus , Amaranthus spp., Basella rubra , Carpobrotus acinaciformis, Centrospermae, Chenopodium formosanum, Chenopodium quinoa , Drosanthemum floribundum, Hylocereus polyrhizus, Mesembryanthemum conspicuum, Mesembryanthemum edule , Mesembryanthemum spp., Opuntia bergeriana, Opuntia elatior, Opuntia ficus-indica , Opuntia vulgaris , Phyllocactus hybridus, Phytolacca acinosa, Portulaca grandiflora , Portulaca jacobseniana, Schlumbergera x buckleyi and Hylocereus monacanthus. This could make gamma-ionone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241215012D          

 39 42  0  0  0  0            999 V2000
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
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  5 16  1  0  0  0  0
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  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
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 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
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 18 19  1  0  0  0  0
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 23 39  1  0  0  0  0
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 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  CHG  2  12  -1  17   1
M  END

     RDKit          3D

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  4  2  1  0
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  2  1  2  0
 35 36  1  0
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 16 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
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 21 18  1  0
 27 14  1  0
  9 10  1  0
  5  6  1  0
 20 50  1  0
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 16 46  1  1
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 11 44  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  1
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 34 61  1  0
 34 62  1  0
 35 63  1  1
 39 65  1  0
  5 41  1  0
  3 40  1  0
 38 64  1  0
 27 57  1  0
 25 55  1  6
 26 56  1  0
 23 53  1  1
 24 54  1  0
 21 51  1  1
 22 52  1  0
M  CHG  2   9   1  33  -1
M  END


  Mrv0541 02241215012D          

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 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 33  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 35  1  0  0  0  0
 23 24  2  0  0  0  0
 23 39  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  CHG  2  12  -1  17   1
M  END
> <DATABASE_ID>
NP0045360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3\CC(NC(=C3)C(O)=O)C(O)=O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)

> <INCHI_KEY>
DHHFDKNIEVKVKS-UHFFFAOYSA-N

> <FORMULA>
C24H26N2O13

> <MOLECULAR_WEIGHT>
550.4688

> <EXACT_MASS>
550.143488928

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
52.966166669239726

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-5.378662464471747

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1284583316632983

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4553895880973071

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395365880728

> <JCHEM_POLAR_SURFACE_AREA>
249.37999999999997

> <JCHEM_REFRACTIVITY>
149.70580000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-1-{2-[(4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.058  -4.599   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.362  -3.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.893  -3.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.966  -4.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.503  -3.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.816  -4.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.207  -3.903   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.521  -4.676   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.681  -5.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.067  -5.990   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.681  -6.686   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.367  -1.971   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      -4.521  -1.584   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.207  -2.357   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.816  -1.584   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.503  -2.357   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.966  -1.893   0.000  0.00  0.00           N+1
HETATM   18  C   UNK     0       1.429  -0.348   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.898  -0.039   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.439   1.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.908   1.739   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.449   3.207   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.995   3.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.000   2.434   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.067  -4.676   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.840  -4.676   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.227  -4.058   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.000  -4.058   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -8.000  -5.372   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.227  -5.372   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.840  -5.990   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.227  -6.686   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.357   2.589   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.898   4.058   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       4.444   4.367   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0       2.357   6.686   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.816   5.217   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.347   4.908   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.458   4.985   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13   14                                                            
CONECT   14    7   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    5   15   17                                                  
CONECT   17    3   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24   39                                                  
CONECT   24   23                                                            
CONECT   25    9   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   26   29   31                                                  
CONECT   31   10   30   32                                                  
CONECT   32   31                                                            
CONECT   33   20   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   22   34                                                       
CONECT   36   37                                                            
CONECT   37   34   36   38                                                  
CONECT   38   37                                                            
CONECT   39   23                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(3E)-4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one	ChEBI
gamma-Ionon	ChEBI
g-Ionon	Generator
Γ-ionon	Generator
g-Ionone	Generator
Γ-ionone	Generator
(3E)-4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-one	HMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one	HMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one, 9ci	HMDB
4-(2-Methylene-6,6-dimethylcyclohexyl)-3-buten-2-one	HMDB
FEMA 3175	HMDB
gamma-Lonone	HMDB
Laquo gammaraquo -ionone	HMDB
Betanine	HMDB
e162	HMDB
Phytolaccanin	HMDB
Betalain pigments	MeSH, HMDB
2-Carboxy-1-[2-(2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene)ethylidene]-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-6-olic acid	Generator

Chemical Formula

C₂₄H₂₆N₂O₁₃

Average Mass

550.4688 Da

Monoisotopic Mass

550.14349 Da

IUPAC Name

(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

Traditional Name

(1E)-1-{2-[(4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate

CAS Registry Number

7659-95-2

SMILES

OCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3\CC(NC(=C3)C(O)=O)C(O)=O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)

InChI Key

DHHFDKNIEVKVKS-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
Amaranthus caudatus	LOTUS Database	35616633
Amaranthus mangostanus	Plant	KNApSAcK
Amaranthus spp.	Plant	KNApSAcK
Basella alba	Plant	KNApSAcK
Beta vulgaris	FooDB	KNAPSACK
Beta vulgaris ssp. cicla	FooDB	PHYTOHUB
Carpobrotus acinaciformis	Plant	KNApSAcK
Centrospermae	-	KNApSAcK
Chenopodium formosanum	LOTUS Database	35616633
Chenopodium quinoa	Plant	KNApSAcK
Drosanthemum floribundum	Plant	KNApSAcK
Hylocereus polyrhizus	Plant	KNApSAcK
Mesembryanthemum conspicuum	Plant	KNApSAcK
Mesembryanthemum edule	Plant	KNApSAcK
Mesembryanthemum spp.	Plant	KNApSAcK
Opuntia	FooDB	PHYTOHUB
Opuntia bergeriana	Plant	KNApSAcK
Opuntia elatior	Plant	KNApSAcK
Opuntia ficus-indica	Plant	KNApSAcK
Opuntia vulgaris	Plant	KNApSAcK
Phyllocactus hybridus	Plant	KNApSAcK
Phytolacca acinosa	LOTUS Database	35616633
Phytolacca americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Portulaca grandiflora	Plant	KNApSAcK
Portulaca jacobseniana	LOTUS Database	35616633
Schlumbergera x buckleyi	Plant	KNApSAcK
Selenicereus monacanthus	LOTUS Database	35616633
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ionone (CHEBI:49250 )

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	0.21	ALOGPS
logP	-5.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	249.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.71 m³·mol⁻¹	ChemAxon
Polarizability	52.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034979

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013578

KNApSAcK ID

Not Available

Chemspider ID

4516050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363741

PDB ID

Not Available

ChEBI ID

49250

Good Scents ID

Not Available

References

General References

Showing NP-Card for Betanin (NP0045360)

MOL for NP0045360 (Betanin)

3D MOL for NP0045360 (Betanin)

3D SDF for NP0045360 (Betanin)

3D-SDF for NP0045360 (Betanin)

PDB for NP0045360 (Betanin)

3D PDB for NP0045360 (Betanin)

SMILES for NP0045360 (Betanin)

INCHI for NP0045360 (Betanin)

Structure for NP0045360 (Betanin)

3D Structure for NP0045360 (Betanin)