NP-MRD: Showing NP-Card for pholiotic acid (NP0025231)

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Record Information

Version

2.0

Created at

2021-06-19 17:24:37 UTC

Updated at

2021-06-29 23:50:01 UTC

NP-MRD ID

NP0025231

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pholiotic acid

Provided By

JEOL Database JEOL Logo

Description

pholiotic acid is found in Pholiota Spumosa. pholiotic acid was first documented in 2007 (Clericuzio, M., et al.). Based on a literature review very few articles have been published on N,N'-[(2R)-2-[[(3S)-3,5-Dihydroxy-3-methyl-1,5-dioxopentyl]oxy]butane-1,4-diyl]bis(cinnamamide).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119243D          

 69 70  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119243D          

 69 70  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0025231

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C(=O)O[C@@]([H])(C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N2O7/c1-28(36,18-26(33)34)19-27(35)37-23(20-30-25(32)15-13-22-10-6-3-7-11-22)16-17-29-24(31)14-12-21-8-4-2-5-9-21/h2-15,23,36H,16-20H2,1H3,(H,29,31)(H,30,32)(H,33,34)/b14-12+,15-13+/t23-,28+/m1/s1

> <INCHI_KEY>
KIIAOYYFHUSITN-MGVJZABTSA-N

> <FORMULA>
C28H32N2O7

> <MOLECULAR_WEIGHT>
508.571

> <EXACT_MASS>
508.220951378

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.263624857206366

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-{[(2R)-1,4-bis[(2E)-3-phenylprop-2-enamido]butan-2-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.2799691613333324

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.65709224526272

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.199607804512284

> <JCHEM_PKA_STRONGEST_BASIC>
-0.03595754477274726

> <JCHEM_POLAR_SURFACE_AREA>
142.03

> <JCHEM_REFRACTIVITY>
139.06199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-{[(2R)-1,4-bis[(2E)-3-phenylprop-2-enamido]butan-2-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.508  -5.290  -2.050  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.661  -4.943  -3.280  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.482  -6.191  -3.999  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.228  -4.511  -2.918  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.117  -3.207  -2.184  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.874  -2.810  -1.314  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.045  -2.494  -2.573  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.348  -3.982  -4.263  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.226  -2.916  -3.656  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.401  -3.089  -3.366  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.552  -1.745  -3.529  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.327  -0.584  -3.154  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.569   0.677  -3.606  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.082   0.737  -3.267  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.811   1.286  -1.957  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.795   0.816  -1.162  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.116  -0.172  -1.422  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.602   1.634   0.062  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.296   1.264   0.988  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.565   1.998   2.235  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.376   2.839   2.846  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.078   3.494   4.045  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.160   3.306   4.655  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.098   2.459   4.070  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.800   1.807   2.870  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.752  -0.577  -1.674  0.00  0.00           C+0
HETATM   27  N   UNK     0      -3.697  -0.866  -0.729  0.00  0.00           N+0
HETATM   28  C   UNK     0      -3.656  -0.296   0.518  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.372   0.630   0.879  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.642  -0.921   1.403  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.576  -0.590   2.702  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.587  -1.141   3.640  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.151  -0.344   4.706  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.217  -0.827   5.625  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.278  -2.122   5.501  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.163  -2.935   4.459  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.094  -2.449   3.537  0.00  0.00           C+0
HETATM   38  H   UNK     0      -3.004  -6.047  -1.437  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.721  -4.426  -1.417  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.465  -5.731  -2.352  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.357  -6.600  -4.130  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.739  -5.280  -2.307  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.636  -4.447  -3.841  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.043  -1.645  -2.051  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.996  -4.544  -4.950  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.614  -3.509  -4.930  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.254  -0.591  -3.746  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.089   1.578  -3.260  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.626   0.689  -4.703  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.593  -0.233  -3.391  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.594   1.424  -3.968  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.342   2.093  -1.657  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.204   2.526   0.169  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.887   0.362   0.836  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.363   2.984   2.413  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.818   4.144   4.505  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.390   3.813   5.588  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.062   2.302   4.547  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.547   1.146   2.436  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.502  -1.356  -1.504  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.230   0.377  -1.426  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.059  -1.634  -0.943  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.954  -1.627   0.957  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.265   0.147   3.111  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.521   0.672   4.821  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.124  -0.188   6.436  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.004  -2.499   6.216  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.214  -3.950   4.365  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.433  -3.111   2.744  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    8    1    4    3                                             
CONECT    3    2   41                                                       
CONECT    4    2    5   42   43                                             
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5   44                                                       
CONECT    8    9    2   45   46                                             
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9                                                       
CONECT   12   11   26   13   47                                             
CONECT   13   12   14   48   49                                             
CONECT   14   13   15   50   51                                             
CONECT   15   14   16   52                                                  
CONECT   16   18   15   17                                                  
CONECT   17   16                                                            
CONECT   18   16   19   53                                                  
CONECT   19   18   20   54                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   55                                                  
CONECT   22   21   23   56                                                  
CONECT   23   22   24   57                                                  
CONECT   24   23   25   58                                                  
CONECT   25   24   20   59                                                  
CONECT   26   27   12   60   61                                             
CONECT   27   28   26   62                                                  
CONECT   28   30   27   29                                                  
CONECT   29   28                                                            
CONECT   30   28   31   63                                                  
CONECT   31   32   30   64                                                  
CONECT   32   37   33   31                                                  
CONECT   33   32   34   65                                                  
CONECT   34   33   35   66                                                  
CONECT   35   36   34   67                                                  
CONECT   36   35   37   68                                                  
CONECT   37   32   36   69                                                  
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   21                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  140    0
END

RDKit          3D

69 70  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂N₂O₇

Average Mass

508.5710 Da

Monoisotopic Mass

508.22095 Da

IUPAC Name

(3S)-5-{[(2R)-1,4-bis[(2E)-3-phenylprop-2-enamido]butan-2-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

(3S)-5-{[(2R)-1,4-bis[(2E)-3-phenylprop-2-enamido]butan-2-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C(=O)O[C@@]([H])(C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

InChI Identifier

InChI=1S/C28H32N2O7/c1-28(36,18-26(33)34)19-27(35)37-23(20-30-25(32)15-13-22-10-6-3-7-11-22)16-17-29-24(31)14-12-21-8-4-2-5-9-21/h2-15,23,36H,16-20H2,1H3,(H,29,31)(H,30,32)(H,33,34)/b14-12+,15-13+/t23-,28+/m1/s1

InChI Key

KIIAOYYFHUSITN-MGVJZABTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pholiota Spumosa	JEOL database	Clericuzio, M., et al, Eur. J. Org. Chem. 2007, 5551..

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen 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	2.41	ALOGPS
logP	2.28	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-0.036	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.03 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	139.06 m³·mol⁻¹	ChemAxon
Polarizability	53.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

28284633

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23652613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Clericuzio, M., et al. (2007). Clericuzio, M., et al, Eur. J. Org. Chem. 2007, 5551... Eur. J. Org. Chem..

Showing NP-Card for pholiotic acid (NP0025231)

MOL for NP0025231 (pholiotic acid )

3D MOL for NP0025231 (pholiotic acid )

3D SDF for NP0025231 (pholiotic acid )

3D-SDF for NP0025231 (pholiotic acid )

PDB for NP0025231 (pholiotic acid )

3D PDB for NP0025231 (pholiotic acid )

SMILES for NP0025231 (pholiotic acid )

INCHI for NP0025231 (pholiotic acid )

Structure for NP0025231 (pholiotic acid )

3D Structure for NP0025231 (pholiotic acid )