NP-MRD: Showing NP-Card for Rosinidin (NP0054448)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 00:48:07 UTC

Updated at

2022-04-28 00:48:08 UTC

NP-MRD ID

NP0054448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rosinidin

Description

Rosinidin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, rosinidin is considered to be a flavonoid lipid molecule. Rosinidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Rosinidin is found in Apis cerana and Primula rosea. An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at positions 3 and 5, a methoxy group at position 7 and a 4-hydroxy-3-methoxyphenyl group at position 2.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.5647    1.0494    1.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4890   -0.1062    0.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3110   -0.6154    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829   -1.7722   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1090   -2.2759   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276   -3.4141   -1.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377   -1.6012   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -2.0240   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4586   -1.3055   -0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7604   -1.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910   -0.1622   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5257    0.6682    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852    1.7940    1.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2922    2.6590    1.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983    2.4282    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6139    3.2888    1.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453    1.3155    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659    1.0882    0.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4594   -0.0447   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    0.4415   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8119    0.1833    0.3952 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.9133   -0.4455    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1118    0.0211    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5837    1.9226    1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    1.1770    2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4943    1.1010    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2225   -2.2656   -0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4002   -3.9113   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.9146   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738   -2.5967   -1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629    1.9829    1.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323    3.5153    2.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5642    3.0640    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5753   -0.0299   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.0136   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2648   -0.9789   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038   -0.4020   -0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    0.9400    1.2500 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 21  2  0
 21 22  1  0
 22 23  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 23  3  1  0
 20 12  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 23 38  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
M  CHG  1  21   1
M  END


  Mrv1533004171520062D          

 23 25  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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   -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
    1.4289    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  3  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 11 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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
M  CHG  1  12   1
M  END
> <DATABASE_ID>
NP0054448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-21-10-6-13(19)11-8-14(20)17(23-15(11)7-10)9-3-4-12(18)16(5-9)22-2/h3-8H,1-2H3,(H2-,18,19,20)/p+1

> <INCHI_KEY>
GNONHFYAESLOCB-UHFFFAOYSA-O

> <FORMULA>
C17H15O6

> <MOLECULAR_WEIGHT>
315.3

> <EXACT_MASS>
315.086314623

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.281581799273006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.1136999999999997

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.952408536468613

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.056173808117801

> <JCHEM_PKA_STRONGEST_BASIC>
-4.588188714914662

> <JCHEM_POLAR_SURFACE_AREA>
92.29

> <JCHEM_REFRACTIVITY>
93.07770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rosinidin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+1
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    3                                                       
CONECT   15   11   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅O₆

Average Mass

315.3000 Da

Monoisotopic Mass

315.08631 Da

IUPAC Name

3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-1λ⁴-chromen-1-ylium

Traditional Name

rosinidin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C17H14O6/c1-21-10-6-13(19)11-8-14(20)17(23-15(11)7-10)9-3-4-12(18)16(5-9)22-2/h3-8H,1-2H3,(H2-,18,19,20)/p+1

InChI Key

GNONHFYAESLOCB-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
Apis cerana	LOTUS Database	35616633
Primula rosea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:8893 )
Anthocyanidins (C08729 )
Anthocyanidins and anthocyanins (C08729 )
Anthocyanidins (LMPK12010417 )

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	2.83	ALOGPS
logP	3.11	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.06	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.08 m³·mol⁻¹	ChemAxon
Polarizability	32.28 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

C00006615

Chemspider ID

Not Available

KEGG Compound ID

C08729

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rosinidin

METLIN ID

Not Available

PubChem Compound

441777

PDB ID

Not Available

ChEBI ID

8893

Good Scents ID

Not Available

References

General References

Showing NP-Card for Rosinidin (NP0054448)

MOL for NP0054448 (Rosinidin)

3D MOL for NP0054448 (Rosinidin)

3D SDF for NP0054448 (Rosinidin)

3D-SDF for NP0054448 (Rosinidin)

PDB for NP0054448 (Rosinidin)

3D PDB for NP0054448 (Rosinidin)

SMILES for NP0054448 (Rosinidin)

INCHI for NP0054448 (Rosinidin)

Structure for NP0054448 (Rosinidin)

3D Structure for NP0054448 (Rosinidin)