NP-MRD: Showing NP-Card for 3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid (NP0279726)

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Record Information

Version

2.0

Created at

2022-09-09 05:13:27 UTC

Updated at

2022-09-09 05:13:27 UTC

NP-MRD ID

NP0279726

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid

Description

ZINC85909260 belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid is found in Blackwellomyces pseudomilitaris and Picea rubens. Based on a literature review very few articles have been published on ZINC85909260.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207132D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092207132D          

 40 42  0  0  1  0            999 V2000
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    2.4655   -7.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505   -7.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -7.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -6.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -6.1034    0.0000 O   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
  3  4  2  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  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
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 12 34  1  0  0  0  0
 34 35  2  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0279726

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C\C1=C(C[C@H](CC)CC2=C(C[C@H](CC)CC3=C(CCC(O)=O)C(=O)OC3=O)C(=O)OC2=O)C(=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O11/c1-4-7-8-17-19(26(34)38-24(17)32)11-15(5-2)13-21-22(29(37)40-28(21)36)14-16(6-3)12-20-18(9-10-23(30)31)25(33)39-27(20)35/h7-8,15-16H,4-6,9-14H2,1-3H3,(H,30,31)/b8-7+/t15-,16+/m0/s1

> <INCHI_KEY>
PHRCULZLDFTOFU-APPUJDCNSA-N

> <FORMULA>
C29H32O11

> <MOLECULAR_WEIGHT>
556.564

> <EXACT_MASS>
556.19446185

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.92037913761483

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{4-[(2R)-2-({4-[(2R)-2-({4-[(1E)-but-1-en-1-yl]-2,5-dioxo-2,5-dihydrofuran-3-yl}methyl)butyl]-2,5-dioxo-2,5-dihydrofuran-3-yl}methyl)butyl]-2,5-dioxo-2,5-dihydrofuran-3-yl}propanoic acid

> <JCHEM_LOGP>
6.018616923666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.172812821257508

> <JCHEM_PKA_STRONGEST_BASIC>
-6.376756856389369

> <JCHEM_POLAR_SURFACE_AREA>
167.40999999999997

> <JCHEM_REFRACTIVITY>
140.03119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{4-[(2R)-2-({4-[(2R)-2-({4-[(1E)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.165  -6.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.499  -7.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.499  -8.654   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.832  -9.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.832 -10.964   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.078 -11.869   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.543 -11.393   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.687 -12.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.367 -13.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.512 -14.960   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.152 -11.948   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.472 -10.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.879  -9.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.213 -10.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.546  -9.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.880 -10.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.880 -12.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.546  -8.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.880  -7.505   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.041  -5.973   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.897  -4.943   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.432  -5.419   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.287  -4.388   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.608  -2.882   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.823  -4.864   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.547  -5.653   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.174  -4.246   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      17.317  -6.987   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.287  -8.131   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.607  -9.638   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.718  -8.283   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.862  -7.253   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.212  -7.963   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.442  -9.297   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.910  -9.458   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.602 -13.333   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.508 -14.579   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       3.062 -13.333   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.586 -11.869   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.122 -11.393   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   34                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   19   30                                                  
CONECT   30   29                                                            
CONECT   31   13   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   12   35                                                  
CONECT   35   34                                                            
CONECT   36    6   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38    5   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₁₁

Average Mass

556.5640 Da

Monoisotopic Mass

556.19446 Da

IUPAC Name

3-{4-[(2R)-2-({4-[(2R)-2-({4-[(1E)-but-1-en-1-yl]-2,5-dioxo-2,5-dihydrofuran-3-yl}methyl)butyl]-2,5-dioxo-2,5-dihydrofuran-3-yl}methyl)butyl]-2,5-dioxo-2,5-dihydrofuran-3-yl}propanoic acid

Traditional Name

3-{4-[(2R)-2-({4-[(2R)-2-({4-[(1E)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C\C1=C(C[C@H](CC)CC2=C(C[C@H](CC)CC3=C(CCC(O)=O)C(=O)OC3=O)C(=O)OC2=O)C(=O)OC1=O

InChI Identifier

InChI=1S/C29H32O11/c1-4-7-8-17-19(26(34)38-24(17)32)11-15(5-2)13-21-22(29(37)40-28(21)36)14-16(6-3)12-20-18(9-10-23(30)31)25(33)39-27(20)35/h7-8,15-16H,4-6,9-14H2,1-3H3,(H,30,31)/b8-7+/t15-,16+/m0/s1

InChI Key

PHRCULZLDFTOFU-APPUJDCNSA-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
Blackwellomyces pseudomilitaris	LOTUS Database	35616633
Picea rubens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Carboxylic acid anhydride
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	6.02	ChemAxon
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	167.41 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	140.03 m³·mol⁻¹	ChemAxon
Polarizability	54.92 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

97046415

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-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid (NP0279726)

MOL for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

3D MOL for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

3D SDF for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

3D-SDF for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

PDB for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

3D PDB for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

SMILES for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

INCHI for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

Structure for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)

3D Structure for NP0279726 (3-{4-[(2r)-2-({4-[(2r)-2-({4-[(1e)-but-1-en-1-yl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}methyl)butyl]-2,5-dioxofuran-3-yl}propanoic acid)