NP-MRD: Showing NP-Card for 2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate (NP0302300)

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Record Information

Version

2.0

Created at

2022-09-10 15:45:50 UTC

Updated at

2022-09-10 15:45:50 UTC

NP-MRD ID

NP0302300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate

Description

Curtisian U belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton. 2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate is found in Paxillus curtisii. Based on a literature review very few articles have been published on Curtisian U.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102217452D          

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   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  6  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  1  0  0  0
 27 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302300

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O12/c1-15(31)13-23(37)41-29-25(19-5-9-21(35)10-6-19)28(40-18(4)34)30(42-24(38)14-16(2)32)26(27(29)39-17(3)33)20-7-11-22(36)12-8-20/h5-12,15-16,31-32,35-36H,13-14H2,1-4H3/t15-,16-/m1/s1

> <INCHI_KEY>
ASLFGEZJFDFJAM-HZPDHXFCSA-N

> <FORMULA>
C30H30O12

> <MOLECULAR_WEIGHT>
582.558

> <EXACT_MASS>
582.173726406

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
58.811420112500144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3R)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3R)-3-hydroxybutanoate

> <JCHEM_LOGP>
2.7622892239999994

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.77333285419289

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.169131488213432

> <JCHEM_PKA_STRONGEST_BASIC>
-2.621000704519779

> <JCHEM_POLAR_SURFACE_AREA>
186.11999999999998

> <JCHEM_REFRACTIVITY>
146.46259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3R)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3R)-3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.499  -6.021   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.833  -5.251   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.965  -2.479   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.667  -4.620   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   35                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27    5   36                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₁₂

Average Mass

582.5580 Da

Monoisotopic Mass

582.17373 Da

IUPAC Name

2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3R)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3R)-3-hydroxybutanoate

Traditional Name

2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3R)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3R)-3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H30O12/c1-15(31)13-23(37)41-29-25(19-5-9-21(35)10-6-19)28(40-18(4)34)30(42-24(38)14-16(2)32)26(27(29)39-17(3)33)20-7-11-22(36)12-8-20/h5-12,15-16,31-32,35-36H,13-14H2,1-4H3/t15-,16-/m1/s1

InChI Key

ASLFGEZJFDFJAM-HZPDHXFCSA-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
Tetracarboxylic acid or derivatives
Biphenyl
Phenol ester
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Fatty acid ester
Phenol
Hydroxy acid
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
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	2.76	ChemAxon
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	186.12 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	146.46 m³·mol⁻¹	ChemAxon
Polarizability	58.81 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

24614790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45268317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate (NP0302300)

MOL for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

3D MOL for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

3D SDF for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

3D-SDF for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

PDB for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

3D PDB for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

SMILES for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

INCHI for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

Structure for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)

3D Structure for NP0302300 (2,5-bis(acetyloxy)-4'-hydroxy-6-{[(3r)-3-hydroxybutanoyl]oxy}-4-(4-hydroxyphenyl)-[1,1'-biphenyl]-3-yl (3r)-3-hydroxybutanoate)