NP-MRD: Showing NP-Card for Nordenletin (NP0063213)

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Record Information

Version

2.0

Created at

2022-04-28 07:40:43 UTC

Updated at

2022-04-28 07:40:44 UTC

NP-MRD ID

NP0063213

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nordenletin

Description

(6R)-5-hydroxy-6-{5-hydroxy-2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-10-yl}-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Nordenletin is found in Citrus hassaku . Based on a literature review very few articles have been published on (6R)-5-hydroxy-6-{5-hydroxy-2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-10-yl}-8,8-dimethyl-10-(2-methylbut-3-en-2-yl)-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209402D          

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M  END

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M  END


  Mrv1652304282209402D          

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    2.8579    3.3000    0.0000 C   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044   -1.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  2  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 21 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 10 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  9 38  1  0  0  0  0
 36 39  1  0  0  0  0
 36 40  1  0  0  0  0
  8 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1=C2OC(=O)C=CC2=C(O)C2=C1OC(C)(C)C[C@H]2C1=C2OC(=O)C=CC2=C(O)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H32O8/c1-8-31(2,3)24-29-17(10-12-21(35)39-29)26(37)22-19(15-33(6,7)41-30(22)24)23-27-16(9-11-20(34)38-27)25(36)18-13-14-32(4,5)40-28(18)23/h8-14,19,36-37H,1,15H2,2-7H3/t19-/m1/s1

> <INCHI_KEY>
FHJQQVOVOMBWAA-LJQANCHMSA-N

> <FORMULA>
C33H32O8

> <MOLECULAR_WEIGHT>
556.611

> <EXACT_MASS>
556.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.42260697159925

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R)-9-hydroxy-11-{5-hydroxy-2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-10-yl}-13,13-dimethyl-2-(2-methylbut-3-en-2-yl)-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
6.017363790333333

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.069243037781357

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.421873901504137

> <JCHEM_PKA_STRONGEST_BASIC>
-4.610497784348951

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000002

> <JCHEM_REFRACTIVITY>
156.7798

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11R)-9-hydroxy-11-{5-hydroxy-2,2-dimethyl-8-oxopyrano[3,2-g]chromen-10-yl}-13,13-dimethyl-2-(2-methylbut-3-en-2-yl)-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-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      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+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  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+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       8.818   2.846   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.541   1.594   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.096  -2.016   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.461   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.541   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.851  -1.774   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.128  -3.026   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   41                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   14   21   30                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30   20   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33                                                            
CONECT   35   10   36                                                       
CONECT   36   35   37   39   40                                             
CONECT   37   36   38                                                       
CONECT   38   37    9                                                       
CONECT   39   36                                                            
CONECT   40   36                                                            
CONECT   41    8                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₂O₈

Average Mass

556.6110 Da

Monoisotopic Mass

556.20972 Da

IUPAC Name

(11R)-9-hydroxy-11-{5-hydroxy-2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-10-yl}-13,13-dimethyl-2-(2-methylbut-3-en-2-yl)-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

Traditional Name

(11R)-9-hydroxy-11-{5-hydroxy-2,2-dimethyl-8-oxopyrano[3,2-g]chromen-10-yl}-13,13-dimethyl-2-(2-methylbut-3-en-2-yl)-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C2OC(=O)C=CC2=C(O)C2=C1OC(C)(C)C[C@H]2C1=C2OC(=O)C=CC2=C(O)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C33H32O8/c1-8-31(2,3)24-29-17(10-12-21(35)39-29)26(37)22-19(15-33(6,7)41-30(22)24)23-27-16(9-11-20(34)38-27)25(36)18-13-14-32(4,5)40-28(18)23/h8-14,19,36-37H,1,15H2,2-7H3/t19-/m1/s1

InChI Key

FHJQQVOVOMBWAA-LJQANCHMSA-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
Citrus hassaku	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranocoumarin
Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
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	5.6	ALOGPS
logP	6.02	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	156.78 m³·mol⁻¹	ChemAxon
Polarizability	58.42 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163022482

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nordenletin (NP0063213)

MOL for NP0063213 (Nordenletin)

3D MOL for NP0063213 (Nordenletin)

3D SDF for NP0063213 (Nordenletin)

3D-SDF for NP0063213 (Nordenletin)

PDB for NP0063213 (Nordenletin)

3D PDB for NP0063213 (Nordenletin)

SMILES for NP0063213 (Nordenletin)

INCHI for NP0063213 (Nordenletin)

Structure for NP0063213 (Nordenletin)

3D Structure for NP0063213 (Nordenletin)