NP-MRD: Showing NP-Card for Annulatin (NP0053014)

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Record Information

Version

2.0

Created at

2022-04-27 23:50:52 UTC

Updated at

2022-04-27 23:50:52 UTC

NP-MRD ID

NP0053014

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Annulatin

Description

Annulatin belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, annulatin is considered to be a flavonoid lipid molecule. Annulatin is an O-methylated flavonol found in the roots of Pteroxygonum giraldii. Annulatin is found in Aegialitis annulata, Cereus jamacaru , Goniothalamus thwaitesii, Mammillaria elongata, Oenothera rosea, Oenothera speciosa and Solanum spp.. Annulatin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.6589   -3.2107    1.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016   -2.5636   -0.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -1.3842   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1192   -0.1417   -0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466    0.1324   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0123    1.4154    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    1.7816    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    3.0591    0.4499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2247    0.8060   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5826    1.1147   -0.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -0.4601   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7090   -1.4589   -0.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4533   -0.8022   -0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6819    0.9234   -0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9626    0.8704    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043    2.0312    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0564    1.9485    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420    3.0927    0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6967    0.7396    0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9836   -0.4676    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049   -1.6222    0.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -0.3587    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -1.4955   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366   -2.6391   -0.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5017   -3.9038    0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2110   -3.8315    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -2.4712    1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875    2.1758    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0954    3.7586    0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9292    2.0347   -0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4296   -2.3819   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2139   -1.8301   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289    2.9984    0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269    3.9987    0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714    0.6764    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139   -2.5347   -0.0137 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 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 23  3  1  0
 13  5  1  0
 22 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
  6 28  1  0
  8 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1652310051715552D          

 24 26  0  0  0  0            999 V2000
    3.5724   -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
    3.5724   -0.4125    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
    0.0000    0.0000    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
    4.2868    0.0000    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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
    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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  5  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  2  0  0  0  0
 23  1  1  0  0  0  0
 23 16  1  0  0  0  0
 24 11  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O8/c1-23-16-14(22)12-8(18)4-7(17)5-11(12)24-15(16)6-2-9(19)13(21)10(20)3-6/h2-5,17-21H,1H3

> <INCHI_KEY>
XWTLYULBWZQAAZ-UHFFFAOYSA-N

> <FORMULA>
C16H12O8

> <MOLECULAR_WEIGHT>
332.264

> <EXACT_MASS>
332.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.449126284194648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-methoxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.9655615316666664

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.746299642587529

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372945878024028

> <JCHEM_PKA_STRONGEST_BASIC>
-4.87518756721642

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
83.5943

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
annulatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       6.668  -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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   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       8.002   1.540   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   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       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    6    9                                                       
CONECT    3    6   10                                                       
CONECT    4    7    8                                                       
CONECT    5    7   11                                                       
CONECT    6    2    3   15                                                  
CONECT    7    4    5   17                                                  
CONECT    8    4   12   18                                                  
CONECT    9    2   13   19                                                  
CONECT   10    3   13   20                                                  
CONECT   11    5   12   24                                                  
CONECT   12    8   11   14                                                  
CONECT   13    9   10   21                                                  
CONECT   14   12   16   22                                                  
CONECT   15    6   16   24                                                  
CONECT   16   14   15   23                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23    1   16                                                       
CONECT   24   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₈

Average Mass

332.2640 Da

Monoisotopic Mass

332.05322 Da

IUPAC Name

5,7-dihydroxy-3-methoxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

annulatin

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H12O8/c1-23-16-14(22)12-8(18)4-7(17)5-11(12)24-15(16)6-2-9(19)13(21)10(20)3-6/h2-5,17-21H,1H3

InChI Key

XWTLYULBWZQAAZ-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
Aegialitis annulata	Plant	KNApSAcK
Cereus jamacaru	-	KNApSAcK
Goniothalamus thwaitesii	Plant	KNApSAcK
Mammillaria elongata	Plant	KNApSAcK
Oenothera rosea	LOTUS Database	35616633
Oenothera speciosa	Plant	KNApSAcK
Solanum spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
3-methoxychromone
Chromone
1-benzopyran
Benzopyran
Benzenetriol
Pyrogallol derivative
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112779 )

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	1.97	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.59 m³·mol⁻¹	ChemAxon
Polarizability	31.45 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

HMDB0152192

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Annulatin

METLIN ID

Not Available

PubChem Compound

44259709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Annulatin (NP0053014)

MOL for NP0053014 (Annulatin)

3D MOL for NP0053014 (Annulatin)

3D SDF for NP0053014 (Annulatin)

3D-SDF for NP0053014 (Annulatin)

PDB for NP0053014 (Annulatin)

3D PDB for NP0053014 (Annulatin)

SMILES for NP0053014 (Annulatin)

INCHI for NP0053014 (Annulatin)

Structure for NP0053014 (Annulatin)

3D Structure for NP0053014 (Annulatin)