NP-MRD: Showing NP-Card for 3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate (NP0245864)

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Record Information

Version

2.0

Created at

2022-09-07 07:06:20 UTC

Updated at

2022-09-07 07:06:20 UTC

NP-MRD ID

NP0245864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate

Description

2,4',5-Trihydroxy-6-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-methylcyclopent-3-ene-1-carboxylate belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton. Based on a literature review very few articles have been published on 2,4',5-trihydroxy-6-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-methylcyclopent-3-ene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072209062D          

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M  END

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M  END


  Mrv1652309072209062D          

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 28 30  2  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
  5 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)CC(=O)OC1=C(C(O)=C(OC(=O)C2CC=C(C)C2)C(=C1O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H28O9/c1-15-3-4-19(13-15)29(36)38-28-24(18-7-11-21(32)12-8-18)25(34)27(37-22(33)14-16(2)30)23(26(28)35)17-5-9-20(31)10-6-17/h3,5-12,16,19,30-32,34-35H,4,13-14H2,1-2H3/t16-,19?/m0/s1

> <INCHI_KEY>
VVDOLPJEDSUPSQ-UCFFOFKASA-N

> <FORMULA>
C29H28O9

> <MOLECULAR_WEIGHT>
520.534

> <EXACT_MASS>
520.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
53.691176830060456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4',6-trihydroxy-5-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate

> <JCHEM_LOGP>
5.954670084666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.679691145250178

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.128904362005358

> <JCHEM_PKA_STRONGEST_BASIC>
-2.621000702805927

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
139.33899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4',6-trihydroxy-5-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.803   1.195   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.803  -0.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.557  -1.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.033  -2.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.573  -2.715   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.478  -3.961   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.010  -3.800   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.852  -5.368   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.757  -6.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.288  -6.452   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.915  -5.046   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.194  -7.698   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.725  -7.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.352  -6.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.883  -5.970   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.788  -7.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.320  -7.054   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.162  -8.622   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.630  -8.783   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.567  -9.105   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.472 -10.351   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.846 -11.758   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.315 -11.919   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.751 -13.004   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.125 -14.411   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.593 -14.572   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.030 -15.657   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.036  -9.266   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.409 -10.673   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.131  -8.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.599  -8.181   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.973  -9.588   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.441  -9.749   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.536  -8.503   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.004  -8.664   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.162  -7.096   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.694  -6.935   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.049  -1.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    9   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
2,4',5-Trihydroxy-6-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-methylcyclopent-3-ene-1-carboxylic acid	Generator

Chemical Formula

C₂₉H₂₈O₉

Average Mass

520.5340 Da

Monoisotopic Mass

520.17333 Da

IUPAC Name

3,4',6-trihydroxy-5-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate

Traditional Name

3,4',6-trihydroxy-5-{[(3S)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@H](O)CC(=O)OC1=C(C(O)=C(OC(=O)C2CC=C(C)C2)C(=C1O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C29H28O9/c1-15-3-4-19(13-15)29(36)38-28-24(18-7-11-21(32)12-8-18)25(34)27(37-22(33)14-16(2)30)23(26(28)35)17-5-9-20(31)10-6-17/h3,5-12,16,19,30-32,34-35H,4,13-14H2,1-2H3/t16-,19?/m0/s1

InChI Key

VVDOLPJEDSUPSQ-UCFFOFKASA-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

Not Available

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
Phenol
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	5.95	ChemAxon
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.34 m³·mol⁻¹	ChemAxon
Polarizability	53.69 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

78441576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139589375

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-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate (NP0245864)

MOL for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

3D MOL for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

3D SDF for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

3D-SDF for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

PDB for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

3D PDB for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

SMILES for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

INCHI for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

Structure for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)

3D Structure for NP0245864 (3,4',6-trihydroxy-5-{[(3s)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-methylcyclopent-3-ene-1-carboxylate)