NP-MRD: Showing NP-Card for 6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid (NP0253641)

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Record Information

Version

2.0

Created at

2022-09-07 17:34:28 UTC

Updated at

2022-09-07 17:34:28 UTC

NP-MRD ID

NP0253641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid

Description

6-Hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. 6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid is found in Coelopogon abraxas and Coelopogon epiphorellus. 6-Hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503552D          

 35 36  0  0  0  0            999 V2000
   -2.1434    2.0625    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
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   -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
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M  END

     RDKit          3D

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M  END


  Mrv1533004201503552D          

 35 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0253641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=C(OC2=CC(O)=CC(CCC(=O)CC)=C2C(=O)OC)C(OC)=CC(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-5-7-8-9-18-23(25(30)31)19(29)14-21(33-3)24(18)35-20-13-17(28)12-15(10-11-16(27)6-2)22(20)26(32)34-4/h12-14,28-29H,5-11H2,1-4H3,(H,30,31)

> <INCHI_KEY>
SGQNLWJQSWFWLJ-UHFFFAOYSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.888775962890755

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
6.423965335333334

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.107339255031858

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6992007742439883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.746659127385809

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
129.53709999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    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                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   14    9   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    7   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoate	Generator
Epiphorellate 2	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Mass

488.5330 Da

Monoisotopic Mass

488.20463 Da

IUPAC Name

6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid

Traditional Name

6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=C(OC2=CC(O)=CC(CCC(=O)CC)=C2C(=O)OC)C(OC)=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C26H32O9/c1-5-7-8-9-18-23(25(30)31)19(29)14-21(33-3)24(18)35-20-13-17(28)12-15(10-11-16(27)6-2)22(20)26(32)34-4/h12-14,28-29H,5-11H2,1-4H3,(H,30,31)

InChI Key

SGQNLWJQSWFWLJ-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
Coelopogon abraxas	LOTUS Database	35616633
Coelopogon epiphorellus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoate ester
Salicylic acid or derivatives
Salicylic acid
Benzoic acid
Benzoic acid or derivatives
Phenol ether
Phenoxy compound
Benzoyl
Methoxybenzene
Anisole
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Dicarboxylic acid or derivatives
Methyl ester
Vinylogous acid
Ketone
Carboxylic acid ester
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.61	ALOGPS
logP	6.42	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	2.7	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	129.54 m³·mol⁻¹	ChemAxon
Polarizability	51.89 Å³	ChemAxon
Number of Rings	2	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

14331493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid (NP0253641)

MOL for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

3D MOL for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

3D SDF for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

3D-SDF for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

PDB for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

3D PDB for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

SMILES for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

INCHI for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

Structure for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)

3D Structure for NP0253641 (6-hydroxy-3-[5-hydroxy-2-(methoxycarbonyl)-3-(3-oxopentyl)phenoxy]-4-methoxy-2-pentylbenzoic acid)