NP-MRD: Showing NP-Card for 3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate (NP0191413)

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Record Information

Version

2.0

Created at

2022-09-04 08:21:55 UTC

Updated at

2022-09-04 08:21:55 UTC

NP-MRD ID

NP0191413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate

Description

2,4',5-Trihydroxy-6-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-(acetyloxy)butanoate 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-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate is found in Paxillus curtisii. 2,4',5-Trihydroxy-6-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-(acetyloxy)butanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511352D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251511352D          

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 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
  8 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
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  2  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
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC(=O)OC1=C(O)C(C2=CC=C(O)C=C2)=C(OC(=O)CC(C)OC(C)=O)C(O)=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O11/c1-14(29)12-21(33)38-27-23(17-4-8-19(31)9-5-17)26(36)28(39-22(34)13-15(2)37-16(3)30)24(25(27)35)18-6-10-20(32)11-7-18/h4-11,14-15,29,31-32,35-36H,12-13H2,1-3H3

> <INCHI_KEY>
PJBCIDYFSJCFFF-UHFFFAOYSA-N

> <FORMULA>
C28H28O11

> <MOLECULAR_WEIGHT>
540.521

> <EXACT_MASS>
540.163161722

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.92976579294484

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-4-[(3-hydroxybutanoyl)oxy]-3,6-bis(4-hydroxyphenyl)phenyl 3-(acetyloxy)butanoate

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
4.681762042333333

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.679879133570257

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.129055822839852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.621000702805927

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
137.31109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-4-[(3-hydroxybutanoyl)oxy]-3,6-bis(4-hydroxyphenyl)phenyl 3-(acetyloxy)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   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  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   12   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    8   26                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
CONECT   33   11   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
2,4',5-Trihydroxy-6-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl 3-(acetyloxy)butanoic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₁

Average Mass

540.5210 Da

Monoisotopic Mass

540.16316 Da

IUPAC Name

2,5-dihydroxy-4-[(3-hydroxybutanoyl)oxy]-3,6-bis(4-hydroxyphenyl)phenyl 3-(acetyloxy)butanoate

Traditional Name

2,5-dihydroxy-4-[(3-hydroxybutanoyl)oxy]-3,6-bis(4-hydroxyphenyl)phenyl 3-(acetyloxy)butanoate

CAS Registry Number

Not Available

SMILES

CC(O)CC(=O)OC1=C(O)C(C2=CC=C(O)C=C2)=C(OC(=O)CC(C)OC(C)=O)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C28H28O11/c1-14(29)12-21(33)38-27-23(17-4-8-19(31)9-5-17)26(36)28(39-22(34)13-15(2)37-16(3)30)24(25(27)35)18-6-10-20(32)11-7-18/h4-11,14-15,29,31-32,35-36H,12-13H2,1-3H3

InChI Key

PJBCIDYFSJCFFF-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
Paxillus curtisii	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
Tricarboxylic acid or derivatives
Phenoxy compound
Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	3.51	ALOGPS
logP	4.68	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.31 m³·mol⁻¹	ChemAxon
Polarizability	54.93 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

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

56663877

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-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate (NP0191413)

MOL for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

3D MOL for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

3D SDF for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

3D-SDF for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

PDB for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

3D PDB for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

SMILES for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

INCHI for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

Structure for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)

3D Structure for NP0191413 (3,4',6-trihydroxy-5-[(3-hydroxybutanoyl)oxy]-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-2-yl 3-(acetyloxy)butanoate)