NP-MRD: Showing NP-Card for 2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile (NP0224010)

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Record Information

Version

2.0

Created at

2022-09-06 02:15:37 UTC

Updated at

2022-09-06 02:15:37 UTC

NP-MRD ID

NP0224010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

Description

2-(3-Hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. 2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile is found in Hydrangea macrophylla. 2-(3-Hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521252D          

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M  END

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M  END


  Mrv1533004231521252D          

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M  END
> <DATABASE_ID>
NP0224010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)C(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO13/c1-31-10-3-2-8(4-9(10)24)11(5-22)33-21-19(30)17(28)15(26)13(35-21)7-32-20-18(29)16(27)14(25)12(6-23)34-20/h2-4,11-21,23-30H,6-7H2,1H3

> <INCHI_KEY>
UCDZCGGWKCRURM-UHFFFAOYSA-N

> <FORMULA>
C21H29NO13

> <MOLECULAR_WEIGHT>
503.457

> <EXACT_MASS>
503.163889998

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.68149404513457

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-3.0491233673333333

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.911498301011722

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.741687171552114

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
231.77999999999997

> <JCHEM_REFRACTIVITY>
110.95380000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002 -21.560   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335 -23.100   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334 -20.790   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -5.335 -15.400   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12   33                                                  
CONECT   33   32                                                            
CONECT   34   10   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉NO₁₃

Average Mass

503.4570 Da

Monoisotopic Mass

503.16389 Da

IUPAC Name

2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

Traditional Name

2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1O)C(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C#N

InChI Identifier

InChI=1S/C21H29NO13/c1-31-10-3-2-8(4-9(10)24)11(5-22)33-21-19(30)17(28)15(26)13(35-21)7-32-20-18(29)16(27)14(25)12(6-23)34-20/h2-4,11-21,23-30H,6-7H2,1H3

InChI Key

UCDZCGGWKCRURM-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
Hydrangea macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Disaccharide
O-glycosyl compound
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Secondary alcohol
Oxacycle
Nitrile
Carbonitrile
Organoheterocyclic compound
Ether
Acetal
Polyol
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
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	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.78 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.95 m³·mol⁻¹	ChemAxon
Polarizability	47.68 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile (NP0224010)

MOL for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D MOL for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D SDF for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D-SDF for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

PDB for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D PDB for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

SMILES for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

INCHI for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

Structure for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)

3D Structure for NP0224010 (2-(3-hydroxy-4-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile)