NP-MRD: Showing NP-Card for 3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate (NP0191871)

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Record Information

Version

2.0

Created at

2022-09-04 08:57:41 UTC

Updated at

2022-09-04 08:57:41 UTC

NP-MRD ID

NP0191871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate

Description

3,4',6-Trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton. 3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate is found in Thelephora aurantiotincta and Thelephora terrestris. Based on a literature review very few articles have been published on 3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210572D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042210572D          

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    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 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  1  0  0  0  0
 14 15  2  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
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 13 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](C)CC(=O)OC1=C(O)C(C2=CC=C(O)C=C2)=C(OC(=O)CC2=CC=CC=C2)C(O)=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H32O8/c1-19(2)20(3)17-26(36)40-32-28(22-9-13-24(34)14-10-22)31(39)33(41-27(37)18-21-7-5-4-6-8-21)29(30(32)38)23-11-15-25(35)16-12-23/h4-16,19-20,34-35,38-39H,17-18H2,1-3H3/t20-/m1/s1

> <INCHI_KEY>
AHONBSJSZASARD-HXUWFJFHSA-N

> <FORMULA>
C33H32O8

> <MOLECULAR_WEIGHT>
556.611

> <EXACT_MASS>
556.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
59.920981267026676

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate

> <JCHEM_LOGP>
8.566008391333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.67984321167798

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.129024266573284

> <JCHEM_PKA_STRONGEST_BASIC>
-4.436882631498535

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
154.16679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21   13   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   10   35                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
3,4',6-Trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoic acid	Generator

Chemical Formula

C₃₃H₃₂O₈

Average Mass

556.6110 Da

Monoisotopic Mass

556.20972 Da

IUPAC Name

3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate

Traditional Name

3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3R)-3,4-dimethylpentanoate

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)CC(=O)OC1=C(O)C(C2=CC=C(O)C=C2)=C(OC(=O)CC2=CC=CC=C2)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C33H32O8/c1-19(2)20(3)17-26(36)40-32-28(22-9-13-24(34)14-10-22)31(39)33(41-27(37)18-21-7-5-4-6-8-21)29(30(32)38)23-11-15-25(35)16-12-23/h4-16,19-20,34-35,38-39H,17-18H2,1-3H3/t20-/m1/s1

InChI Key

AHONBSJSZASARD-HXUWFJFHSA-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
Thelephora aurantiotincta	LOTUS Database	35616633
Thelephora terrestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Terphenyls

Direct Parent

P-terphenyls

Alternative Parents

Substituents

Para-terphenyl
Biphenyl
Phenol ester
Phenoxy compound
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Dicarboxylic acid or derivatives
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen 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	8.57	ChemAxon
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	154.17 m³·mol⁻¹	ChemAxon
Polarizability	59.92 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

162896035

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate (NP0191871)

MOL for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

3D MOL for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

3D SDF for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

3D-SDF for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

PDB for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

3D PDB for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

SMILES for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

INCHI for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

Structure for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)

3D Structure for NP0191871 (3,4',6-trihydroxy-4-(4-hydroxyphenyl)-5-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-2-yl (3r)-3,4-dimethylpentanoate)