NP-MRD: Showing NP-Card for 6-Hydroxycyanidin (NP0054449)

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Record Information

Version

2.0

Created at

2022-04-28 00:48:09 UTC

Updated at

2022-04-28 00:48:09 UTC

NP-MRD ID

NP0054449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxycyanidin

Description

2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1λ⁴-chromen-1-ylium, also known as quercetagetinidin, belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1λ⁴-chromen-1-ylium is considered to be a flavonoid lipid molecule. An anthocyanidin cation that is cyanidin substituted by a hydroxy group at position 6. 6-Hydroxycyanidin is found in Alstroemeria spp. 2-(3,4-Dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1λ⁴-chromen-1-ylium is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.8322    1.4586    0.7099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5347    1.0319    0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    1.7209    0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1921    1.2886    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    0.1580   -0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -0.2320   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578    0.5143    0.1741 O   0  0  0  0  0  3  0  0  0  0  0  0
    1.6337    0.3118    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682    1.1432    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159    0.9142    0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8736    1.7319    1.1363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154   -0.1654   -0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -0.3912   -0.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3899   -0.9882   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7824   -2.0819   -1.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234   -0.7701   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967   -1.5850   -1.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.3151   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -2.1470   -1.7483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578   -0.5209   -0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3641   -0.0828   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -0.7868   -0.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0073    2.2768    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6001    2.6107    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.8015    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2392    1.9917    1.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428    2.5216    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    0.2027    0.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -2.2596   -1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3898   -2.4318   -1.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9600   -2.9365   -2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584   -1.3947   -1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2567   -1.5893   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
  6  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 21  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
 12 10  1  0
  4  5  1  0
 16  8  1  0
 11 27  1  0
  9 26  1  0
 19 31  1  0
 17 30  1  0
 15 29  1  0
 13 28  1  0
 20 32  1  0
 22 33  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
M  CHG  1   7   1
M  END


  Mrv1652308211923032D          

 22 24  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
    0.0000    2.4750    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
   -1.4289    0.8250    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
   -2.8579    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
    2.1434    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
    0.7145    1.2375    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
    2.1434    2.0625    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
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    1.4289    3.3000    0.0000 O   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
    0.0000    0.8250    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  1  0  0  0  0
 15 11  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  2  0  0  0  0
 22 15  1  0  0  0  0
M  CHG  1  22   1
M  END
> <DATABASE_ID>
NP0054449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=[O+]C(=C(O)C=C2C(O)=C1O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-8-2-1-6(3-9(8)17)15-11(19)4-7-12(22-15)5-10(18)14(21)13(7)20/h1-5H,(H5-,16,17,18,19,20,21)/p+1

> <INCHI_KEY>
PWDAKBACEAGRSH-UHFFFAOYSA-O

> <FORMULA>
C15H11O7

> <MOLECULAR_WEIGHT>
303.245

> <EXACT_MASS>
303.049929114

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.060955627282954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
2.7659

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.6605499915387

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.538406592755488

> <JCHEM_PKA_STRONGEST_BASIC>
-6.245947244686836

> <JCHEM_POLAR_SURFACE_AREA>
134.52

> <JCHEM_REFRACTIVITY>
86.09400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+1
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   11                                                       
CONECT    5   10   12                                                       
CONECT    6    1    3   15                                                  
CONECT    7    4   12   13                                                  
CONECT    8    2    9   16                                                  
CONECT    9    3    8   17                                                  
CONECT   10    5   14   18                                                  
CONECT   11    4   15   19                                                  
CONECT   12    5    7   22                                                  
CONECT   13    7   14   20                                                  
CONECT   14   10   13   21                                                  
CONECT   15    6   11   22                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Quercetagetinidin	ChEBI

Chemical Formula

C₁₅H₁₁O₇

Average Mass

303.2450 Da

Monoisotopic Mass

303.04993 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1lambda4-chromen-1-ylium

Traditional Name

2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxy-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

OC1=CC2=[O+]C(=C(O)C=C2C(O)=C1O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O7/c16-8-2-1-6(3-9(8)17)15-11(19)4-7-12(22-15)5-10(18)14(21)13(7)20/h1-5H,(H5-,16,17,18,19,20,21)/p+1

InChI Key

PWDAKBACEAGRSH-UHFFFAOYSA-O

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
Alstroemeria spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:28090 )
Anthocyanidins (LMPK12010428 )

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	1.49	ALOGPS
logP	2.77	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	134.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.09 m³·mol⁻¹	ChemAxon
Polarizability	29.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon