NP-MRD: Showing NP-Card for 4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid (NP0150620)

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Record Information

Version

2.0

Created at

2022-09-02 06:47:29 UTC

Updated at

2022-09-02 06:47:29 UTC

NP-MRD ID

NP0150620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid

Description

CHEMBL4098715, also known as trivaric acid, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid is found in Ramalina americana. Based on a literature review very few articles have been published on CHEMBL4098715.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208472D          

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M  END

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  Mrv1652309022208472D          

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    0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  2  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  6 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
  4 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(O)=CC(O)=C1C(=O)OC1=CC(O)=C(C(=O)OC2=CC(O)=C(C(O)=O)C(CCC)=C2)C(CCC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O10/c1-4-7-16-10-19(31)13-22(32)26(16)29(37)40-21-12-18(9-6-3)27(24(34)15-21)30(38)39-20-11-17(8-5-2)25(28(35)36)23(33)14-20/h10-15,31-34H,4-9H2,1-3H3,(H,35,36)

> <INCHI_KEY>
PABQFZVSLPCEQH-UHFFFAOYSA-N

> <FORMULA>
C30H32O10

> <MOLECULAR_WEIGHT>
552.576

> <EXACT_MASS>
552.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
57.512168400273154

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
9.897114420666666

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.532729315467996

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7983537565111734

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0076837792392555

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
147.5732

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.338 -14.630   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.005 -19.250   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   30                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   14   30                                                       
CONECT   30   29   10   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34    6   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    4   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
Trivaric acid	MeSH

Chemical Formula

C₃₀H₃₂O₁₀

Average Mass

552.5760 Da

Monoisotopic Mass

552.19955 Da

IUPAC Name

4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid

Traditional Name

4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCC1=CC(O)=CC(O)=C1C(=O)OC1=CC(O)=C(C(=O)OC2=CC(O)=C(C(O)=O)C(CCC)=C2)C(CCC)=C1

InChI Identifier

InChI=1S/C30H32O10/c1-4-7-16-10-19(31)13-22(32)26(16)29(37)40-21-12-18(9-6-3)27(24(34)15-21)30(38)39-20-11-17(8-5-2)25(28(35)36)23(33)14-20/h10-15,31-34H,4-9H2,1-3H3,(H,35,36)

InChI Key

PABQFZVSLPCEQH-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
Ramalina americana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Phenol ester
Salicylic acid or derivatives
Salicylic acid
Benzoate ester
Phenylpropane
Benzoic acid
Benzoic acid or derivatives
Benzoyl
Resorcinol
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	5.2	ALOGPS
logP	9.9	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	147.57 m³·mol⁻¹	ChemAxon
Polarizability	57.51 Å³	ChemAxon
Number of Rings	3	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

76765780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102307785

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid (NP0150620)

MOL for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

3D MOL for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

3D SDF for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

3D-SDF for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

PDB for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

3D PDB for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

SMILES for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

INCHI for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

Structure for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)

3D Structure for NP0150620 (4-[4-(2,4-dihydroxy-6-propylbenzoyloxy)-2-hydroxy-6-propylbenzoyloxy]-2-hydroxy-6-propylbenzoic acid)