NP-MRD: Showing NP-Card for 5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione (NP0149260)

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Record Information

Version

2.0

Created at

2022-09-02 05:07:47 UTC

Updated at

2022-09-02 05:07:47 UTC

NP-MRD ID

NP0149260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione

Description

5,13,17-Trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]Nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. 5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione is found in Parmotrema arnoldii. 5,13,17-Trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]Nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518392D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161518392D          

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  6  8  1  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
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 14 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
 16 37  1  0  0  0  0
 25 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0149260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)CC1=CC(O)=CC2=C1C(=O)OC1=C(O2)C2=C(C(=O)OC(O)(CCCCC)C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O9/c1-3-5-7-9-17(29)11-16-12-18(30)13-21-23(16)26(32)36-22-14-20(31)24-19(25(22)35-21)15-28(34,37-27(24)33)10-8-6-4-2/h12-14,30-31,34H,3-11,15H2,1-2H3

> <INCHI_KEY>
WXVYEDQSVKIIFW-UHFFFAOYSA-N

> <FORMULA>
C28H32O9

> <MOLECULAR_WEIGHT>
512.555

> <EXACT_MASS>
512.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.10710324910421

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
6.475289517666669

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.324080628833181

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.006591819490223

> <JCHEM_PKA_STRONGEST_BASIC>
-3.79244489835099

> <JCHEM_POLAR_SURFACE_AREA>
139.59000000000003

> <JCHEM_REFRACTIVITY>
135.06289999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.685  -2.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.018  -2.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.352  -2.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.686  -2.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.019  -2.976   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.353  -2.206   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.353  -0.666   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.687  -2.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.020  -2.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.020  -0.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.354   0.104   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.354   1.644   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.688  -0.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.688  -2.206   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.121  -2.769   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      21.575  -4.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.708  -5.513   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.172  -5.628   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.125  -4.499   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.653  -4.953   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.354  -2.976   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.376  -6.900   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.912  -7.015   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      23.580  -8.403   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.779  -5.743   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.315  -5.858   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      25.983  -7.246   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      26.182  -4.586   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      25.514  -3.198   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      26.997  -2.781   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      25.361  -1.666   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.611  -0.767   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.458   0.766   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.708   1.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      29.112   1.031   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.978  -3.083   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      23.111  -4.355   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    9   14                                                  
CONECT   22   17   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   37                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31   36                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   29   37                                                       
CONECT   37   36   16   25                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₉

Average Mass

512.5550 Da

Monoisotopic Mass

512.20463 Da

IUPAC Name

5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione

Traditional Name

5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(11),3(8),4,6,12,14(19)-hexaene-9,15-dione

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)CC1=CC(O)=CC2=C1C(=O)OC1=C(O2)C2=C(C(=O)OC(O)(CCCCC)C2)C(O)=C1

InChI Identifier

InChI=1S/C28H32O9/c1-3-5-7-9-17(29)11-16-12-18(30)13-21-23(16)26(32)36-22-14-20(31)24-19(25(22)35-21)15-28(34,37-27(24)33)10-8-6-4-2/h12-14,30-31,34H,3-11,15H2,1-2H3

InChI Key

WXVYEDQSVKIIFW-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
Parmotrema arnoldii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Benzopyran
Isochromane
2-benzopyran
1-hydroxy-2-unsubstituted benzenoid
1,4-dioxepine
Dioxepine
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	4.57	ALOGPS
logP	6.48	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	135.06 m³·mol⁻¹	ChemAxon
Polarizability	54.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

102267539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione (NP0149260)

MOL for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

3D MOL for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

3D SDF for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

3D-SDF for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

PDB for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

3D PDB for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

SMILES for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

INCHI for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

Structure for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)

3D Structure for NP0149260 (5,13,17-trihydroxy-7-(2-oxoheptyl)-17-pentyl-2,10,16-trioxatetracyclo[9.8.0.0³,⁸.0¹⁴,¹⁹]nonadeca-1(19),3(8),4,6,11,13-hexaene-9,15-dione)