NP-MRD: Showing NP-Card for (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate (NP0186122)

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Record Information

Version

2.0

Created at

2022-09-04 01:49:37 UTC

Updated at

2022-09-04 01:49:37 UTC

NP-MRD ID

NP0186122

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate

Description

(5-{[4,5-Dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate is found in Cucurbita pepo. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502102D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261502102D          

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  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
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 21 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
 16 37  1  0  0  0  0
 12 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186122

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(C=C1)C(=O)OCC1(O)COC(OC2C(O)C(O)C(CO)OC2OC2=CC=C(CO)C=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO12/c26-15-5-3-14(4-6-15)22(32)34-11-25(33)12-35-24(21(25)31)38-20-19(30)18(29)17(10-28)37-23(20)36-16-7-1-13(9-27)2-8-16/h1-8,17-21,23-24,27-31,33H,9-12,26H2

> <INCHI_KEY>
GDKZNHGIXKBQNU-UHFFFAOYSA-N

> <FORMULA>
C25H31NO12

> <MOLECULAR_WEIGHT>
537.518

> <EXACT_MASS>
537.184625442

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.46567917726125

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.975862531666666

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.643777202100072

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.792758221955314

> <JCHEM_PKA_STRONGEST_BASIC>
2.640107515478507

> <JCHEM_POLAR_SURFACE_AREA>
210.61999999999998

> <JCHEM_REFRACTIVITY>
128.19180000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  N   UNK     0       1.652   2.682   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.176   1.217   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.207   0.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.731  -1.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.225  -1.712   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.806  -0.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.330   0.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.251  -3.176   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.758  -3.497   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.779  -4.321   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.303  -5.786   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.364  -5.786   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.564  -9.300   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.009 -10.546   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.382 -11.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.288 -13.198   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.819 -13.037   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.724 -14.283   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.256 -14.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.161 -15.368   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.535 -16.775   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.440 -18.021   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.972 -17.860   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.003 -16.936   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.098 -15.690   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.661 -14.605   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.130 -14.766   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.503 -16.173   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.028 -16.334   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.225 -13.520   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.307 -13.681   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.851 -12.114   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.054 -10.868   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.580  -7.835   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.044  -7.359   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   37                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   21                                                       
CONECT   29   19   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   18   36                                                  
CONECT   36   35                                                            
CONECT   37   16   12   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoic acid	Generator

Chemical Formula

C₂₅H₃₁NO₁₂

Average Mass

537.5180 Da

Monoisotopic Mass

537.18463 Da

IUPAC Name

(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate

Traditional Name

(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate

CAS Registry Number

Not Available

SMILES

NC1=CC=C(C=C1)C(=O)OCC1(O)COC(OC2C(O)C(O)C(CO)OC2OC2=CC=C(CO)C=C2)C1O

InChI Identifier

InChI=1S/C25H31NO12/c26-15-5-3-14(4-6-15)22(32)34-11-25(33)12-35-24(21(25)31)38-20-19(30)18(29)17(10-28)37-23(20)36-16-7-1-13(9-27)2-8-16/h1-8,17-21,23-24,27-31,33H,9-12,26H2

InChI Key

GDKZNHGIXKBQNU-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
Cucurbita pepo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Disaccharide
O-glycosyl compound
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Aniline or substituted anilines
Benzyl alcohol
Phenol ether
Monocyclic benzene moiety
Benzenoid
Oxane
Primary aromatic amine
Tertiary alcohol
Oxolane
Amino acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Aromatic alcohol
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Alcohol
Amine
Primary amine
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	-0.5	ALOGPS
logP	-0.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	2.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	210.62 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.19 m³·mol⁻¹	ChemAxon
Polarizability	54.47 Å³	ChemAxon
Number of Rings	4	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

72992449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate (NP0186122)

MOL for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

3D MOL for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

3D SDF for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

3D-SDF for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

PDB for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

3D PDB for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

SMILES for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

INCHI for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

Structure for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)

3D Structure for NP0186122 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-aminobenzoate)