NP-MRD: Showing NP-Card for Isookanin (NP0055613)

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Record Information

Version

2.0

Created at

2022-04-28 01:36:37 UTC

Updated at

2022-04-28 01:36:37 UTC

NP-MRD ID

NP0055613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isookanin

Description

Isookanin belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Isookanin is found in Acacia confusa, Acacia melanoxylon, Acacia papyrocarpa, Acacia spp. , Albizia julibrissin and Canarium album. Isookanin was first documented in 2021 (PMID: 33787148). Based on a literature review a small amount of articles have been published on Isookanin (PMID: 34747287) (PMID: 34209556) (PMID: 34208772) (PMID: 33419109).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
    1.0416   -3.6436   -0.4731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8883   -2.4385   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635   -1.8193   -0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726   -0.4500   -0.7750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6180    0.3868   -0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369    1.7406   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    2.4872   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582    1.9153    0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039    2.7192    1.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339    0.5619    0.8767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7680   -0.0636    1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6652   -0.1761    0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    0.2783   -0.5061 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -0.2331   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -1.5964   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -2.1233    0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3615   -1.2806    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580    0.0875    0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3243    0.9452    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214    0.5880    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    1.9370   -0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1661   -2.5161   -0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7247   -1.8216    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.5750   -1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8095    2.1868   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6877    3.5567   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5514    2.2822    1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -1.0585    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -1.2504    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573   -3.1916    0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154   -1.7252    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1731    1.9347    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683    2.3555   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 12  1  0
 12 10  2  0
 10 11  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 14  2  0
 14 13  1  0
 10  8  1  0
 13  4  1  0
 14 15  1  0
  9 27  1  0
  7 26  1  0
  6 25  1  0
 12 29  1  0
 11 28  1  0
  4 24  1  6
  3 22  1  0
  3 23  1  0
 16 30  1  0
 17 31  1  0
 19 32  1  0
 21 33  1  0
M  END


  Mrv1652304282203362D          

 21 23  0  0  1  0            999 V2000
   -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
    0.0000   -1.6500    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
    0.7145   -0.4125    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
    0.0000    0.8250    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
    2.1434   -0.4125    0.0000 C   0  0  1  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
    1.4289   -2.4750    0.0000 O   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
    2.8579    0.8250    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    0.8250    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
    3.5724   -0.4125    0.0000 C   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    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  6  0  0  0
 13 14  2  0  0  0  0
 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
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=CC=C(O)C(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-9-3-1-7(5-12(9)19)13-6-11(18)8-2-4-10(17)14(20)15(8)21-13/h1-5,13,16-17,19-20H,6H2/t13-/m0/s1

> <INCHI_KEY>
ZPVNWCMRCGXRJD-ZDUSSCGKSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.298515669803564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.8815427286666666

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.238526991271323

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.983755288506488

> <JCHEM_PKA_STRONGEST_BASIC>
-5.005852968951803

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.27070000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2550 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

(2S)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=CC=C(O)C(O)=C2O1

InChI Identifier

InChI=1S/C15H12O6/c16-9-3-1-7(5-12(9)19)13-6-11(18)8-2-4-10(17)14(20)15(8)21-13/h1-5,13,16-17,19-20H,6H2/t13-/m0/s1

InChI Key

ZPVNWCMRCGXRJD-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, 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
Acacia confusa	LOTUS Database	35616633
Acacia melanoxylon	LOTUS Database	35616633
Acacia papyrocarpa	LOTUS Database	35616633
Acacia spp.	Plant	KNApSAcK
Albizia julibrissin	LOTUS Database	35616633
Canarium album	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
Hydroxyflavonoid
8-hydroxyflavonoid
7-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.14	ALOGPS
logP	1.88	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.27 m³·mol⁻¹	ChemAxon
Polarizability	27.3 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

C00008281

Chemspider ID

65014382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91196552

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Luo L, Zhang YS, Liu XY, Wang SZ, Li ZM, Yao XC: [Study on rat intestinal absorption characteristics of total flavonoids from Coreopsis tinctoria]. Zhongguo Zhong Yao Za Zhi. 2021 Mar;46(6):1490-1497. doi: 10.19540/j.cnki.cjcmm.20200706.202. [PubMed:33787148 ]
Cai FJ, Li CH, Sun XH, Wang L, Tian JL, Zhao W, Kong DG, Liu Q, Zhou HL: A new dihydroflavone and a new polyacetylene glucoside from Bidens parviflora. J Asian Nat Prod Res. 2021 Nov 8:1-8. doi: 10.1080/10286020.2021.1998010. [PubMed:34747287 ]
Zannella C, Giugliano R, Chianese A, Buonocore C, Vitale GA, Sanna G, Sarno F, Manzin A, Nebbioso A, Termolino P, Altucci L, Galdiero M, de Pascale D, Franci G: Antiviral Activity of Vitis vinifera Leaf Extract against SARS-CoV-2 and HSV-1. Viruses. 2021 Jun 29;13(7). pii: v13071263. doi: 10.3390/v13071263. [PubMed:34209556 ]
Xin Y, Roh K, Cho E, Park D, Whang W, Jung E: Isookanin Inhibits PGE2-Mediated Angiogenesis by Inducing Cell Arrest through Inhibiting the Phosphorylation of ERK1/2 and CREB in HMEC-1 Cells. Int J Mol Sci. 2021 Jun 16;22(12). pii: ijms22126466. doi: 10.3390/ijms22126466. [PubMed:34208772 ]
Xin YJ, Choi S, Roh KB, Cho E, Ji H, Weon JB, Park D, Whang WK, Jung E: Anti-Inflammatory Activity and Mechanism of Isookanin, Isolated by Bioassay-Guided Fractionation from Bidens pilosa L. Molecules. 2021 Jan 6;26(2). pii: molecules26020255. doi: 10.3390/molecules26020255. [PubMed:33419109 ]

Showing NP-Card for Isookanin (NP0055613)

MOL for NP0055613 (Isookanin)

3D MOL for NP0055613 (Isookanin)

3D SDF for NP0055613 (Isookanin)

3D-SDF for NP0055613 (Isookanin)

PDB for NP0055613 (Isookanin)

3D PDB for NP0055613 (Isookanin)

SMILES for NP0055613 (Isookanin)

INCHI for NP0055613 (Isookanin)

Structure for NP0055613 (Isookanin)

3D Structure for NP0055613 (Isookanin)