NP-MRD: Showing NP-Card for 10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one (NP0190438)

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Record Information

Version

2.0

Created at

2022-09-04 07:06:32 UTC

Updated at

2022-09-04 07:06:32 UTC

NP-MRD ID

NP0190438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one

Description

10-({2,2-Dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. 10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one is found in Citrus hassaku. 10-({2,2-Dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-2H,8H,9H,10H-pyrano[2,3-h]chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518332D          

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M  END

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  Mrv1533004231518332D          

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M  END
> <DATABASE_ID>
NP0190438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC3=C(C=CC(=O)O3)C(OC3C(O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O8/c1-27(2)12-11-16-19(35-27)13-18-15(7-10-20(29)32-18)24(16)34-25-22-17(36-28(3,4)26(25)31)8-5-14-6-9-21(30)33-23(14)22/h5-13,25-26,31H,1-4H3

> <INCHI_KEY>
KULXGDVSYFDVNX-UHFFFAOYSA-N

> <FORMULA>
C28H24O8

> <MOLECULAR_WEIGHT>
488.492

> <EXACT_MASS>
488.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.42509596175055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-({2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-4-one

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
3.8582862803333335

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.828232744754057

> <JCHEM_PKA_STRONGEST_BASIC>
-3.748730997444576

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000002

> <JCHEM_REFRACTIVITY>
131.6923

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       7.475  -1.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.485   0.267   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.431   2.604   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.485   4.887   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.475   3.173   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   36                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32   16   23                                                  
CONECT   34   14    5   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₄O₈

Average Mass

488.4920 Da

Monoisotopic Mass

488.14712 Da

IUPAC Name

14-({2,2-dimethyl-8-oxo-2H,8H-pyrano[3,2-g]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-4-one

Traditional Name

14-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,5,7,9-tetraen-4-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC3=C(C=CC(=O)O3)C(OC3C(O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)=C2C=C1

InChI Identifier

InChI=1S/C28H24O8/c1-27(2)12-11-16-19(35-27)13-18-15(7-10-20(29)32-18)24(16)34-25-22-17(36-28(3,4)26(25)31)8-5-14-6-9-21(30)33-23(14)22/h5-13,25-26,31H,1-4H3

InChI Key

KULXGDVSYFDVNX-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.31	ALOGPS
logP	3.86	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.69 m³·mol⁻¹	ChemAxon
Polarizability	48.43 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

73821005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one (NP0190438)

MOL for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D MOL for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D SDF for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D-SDF for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

PDB for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D PDB for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

SMILES for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

INCHI for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

Structure for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D Structure for NP0190438 (10-({2,2-dimethyl-8-oxopyrano[3,2-g]chromen-5-yl}oxy)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)