NP-MRD: Showing NP-Card for {3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid (NP0321709)

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Record Information

Version

1.0

Created at

2022-09-12 00:03:59 UTC

Updated at

2022-09-12 00:03:59 UTC

NP-MRD ID

NP0321709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid

Description

2-{3-Oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. {3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid is found in Pimenta dioica. 2-{3-Oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500082D          

 38 40  0  0  0  0            999 V2000
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   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004181500082D          

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  5  6  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  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
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  2  0  0  0  0
 20 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OCCC=CCC2C(CC(O)=O)CCC2=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O13/c26-15-6-5-12(10-19(29)30)14(15)4-2-1-3-7-36-25-23(34)22(33)21(32)18(38-25)11-37-24(35)13-8-16(27)20(31)17(28)9-13/h1-2,8-9,12,14,18,21-23,25,27-28,31-34H,3-7,10-11H2,(H,29,30)

> <INCHI_KEY>
YNGJOPKAULIOQY-UHFFFAOYSA-N

> <FORMULA>
C25H32O13

> <MOLECULAR_WEIGHT>
540.518

> <EXACT_MASS>
540.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.961344264434175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
0.7914004989999996

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.10796476602828

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.462530432825825

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490924340554898

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
128.6632

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.580 -17.075   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.044 -16.599   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.189 -17.630   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.868 -19.136   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.653 -17.154   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.104 -18.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.564 -18.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.088 -17.075   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.377 -16.599   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10                                                       
CONECT   19    5   20                                                       
CONECT   20   19   21   37                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   27   36                                                  
CONECT   36   35                                                            
CONECT   37   20    2   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetate	Generator

Chemical Formula

C₂₅H₃₂O₁₃

Average Mass

540.5180 Da

Monoisotopic Mass

540.18429 Da

IUPAC Name

2-{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid

Traditional Name

{3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OCCC=CCC2C(CC(O)=O)CCC2=O)C(O)C1O

InChI Identifier

InChI=1S/C25H32O13/c26-15-6-5-12(10-19(29)30)14(15)4-2-1-3-7-36-25-23(34)22(33)21(32)18(38-25)11-37-24(35)13-8-16(27)20(31)17(28)9-13/h1-2,8-9,12,14,18,21-23,25,27-28,31-34H,3-7,10-11H2,(H,29,30)

InChI Key

YNGJOPKAULIOQY-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
Pimenta dioica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Jasmonic acid
Fatty acyl glycoside of mono- or disaccharide
Galloyl ester
Alkyl glycoside
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1.14	ALOGPS
logP	0.79	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	128.66 m³·mol⁻¹	ChemAxon
Polarizability	53.96 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

74342823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid (NP0321709)

MOL for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

3D MOL for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

3D SDF for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

3D-SDF for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

PDB for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

3D PDB for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

SMILES for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

INCHI for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

Structure for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)

3D Structure for NP0321709 ({3-oxo-2-[5-({3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl}oxy)pent-2-en-1-yl]cyclopentyl}acetic acid)