NP-MRD: Showing NP-Card for dhurrin (NP0249922)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 12:37:02 UTC

Updated at

2022-09-07 12:37:02 UTC

NP-MRD ID

NP0249922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dhurrin

Description

Taxiphyllin, also known as phyllanthin?, Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Taxiphyllin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Taxiphyllin has been detected, but not quantified in, several different foods, such as canola, dates, sea-buckthornberries, highbush blueberries, and black walnuts. This could make taxiphyllin a potential biomarker for the consumption of these foods. dhurrin is found in Bambusa vulgaris, Campylospermum flavum, Cercocarpus ledifolius, Chamaebatia foliolosa, Henriettea fascicularis, Hydrangea macrophylla, Ostrya virginiana, Sorghum arundinaceum, Sorghum bicolor and Suckleya suckleyana. dhurrin was first documented in 1979 (PMID: 16660850). Taxiphyllin is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.3618    1.2757   -2.9336 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0364    0.9375   -1.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5993    0.4662   -0.5136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4865   -0.3355   -0.7410 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6960    0.2947   -0.3578 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4159    0.5129   -1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554    1.0088   -1.4414 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4556    0.5080   -2.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7590    0.9893   -2.6201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492    0.7496   -0.2087 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3097    1.8377    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6418    0.5256    1.0230 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0048    1.6669    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -0.4577    0.6320 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8625   -0.9032    1.7503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7265   -0.3488   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -0.0892   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0670   -0.8342   -0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9577   -1.8533    0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0625   -2.5878    1.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974   -2.1179    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -1.3722    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4037    1.4044    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4166    1.2820    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    2.1301   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5106   -0.6111   -2.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0060    0.7923   -3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825    1.9370   -2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1248   -0.1267   -0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613    1.5521    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2916    0.0473    1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8512    1.5722    2.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -1.2956    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739   -1.8749    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    0.7197   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0784   -0.6336   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5526   -2.2137    2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863   -2.9250    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -1.6294    1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  5 14  1  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  7  1  0
 22 16  1  0
  9 28  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  6
  5 24  1  1
  3 23  1  1
 17 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 14 33  1  6
 15 34  1  0
 12 31  1  1
 13 32  1  0
 10 29  1  6
 11 30  1  0
M  END


  Mrv0541 02241205482D          

 22 23  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  3  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC(C#N)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2

> <INCHI_KEY>
NVLTYOJHPBMILU-UHFFFAOYSA-N

> <FORMULA>
C14H17NO7

> <MOLECULAR_WEIGHT>
311.2873

> <EXACT_MASS>
311.100501903

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
30.199048395983226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-1.1206164559999992

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208896083272556

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.456334194181542

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084265018608

> <JCHEM_POLAR_SURFACE_AREA>
143.4

> <JCHEM_REFRACTIVITY>
72.0773

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dhurrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   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       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.668  -3.850   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(R)-4-Hydroxymandelonitrile beta-D-glucoside	HMDB
(R)-p-Hydroxymandelonitrile-D-glucopyranoside	HMDB
Phyllanthin?	HMDB
Phyllanthoside?	HMDB

Chemical Formula

C₁₄H₁₇NO₇

Average Mass

311.2873 Da

Monoisotopic Mass

311.10050 Da

IUPAC Name

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

Traditional Name

dhurrin

CAS Registry Number

Not Available

SMILES

OCC1OC(OC(C#N)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2

InChI Key

NVLTYOJHPBMILU-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
Bambusa vulgaris	LOTUS Database	35616633
Campylospermum flavum	LOTUS Database	35616633
Cercocarpus ledifolius	LOTUS Database	35616633
Chamaebatia foliolosa	LOTUS Database	35616633
Henriettea fascicularis	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Ostrya virginiana	LOTUS Database	35616633
Sorghum arundinaceum	LOTUS Database	35616633
Sorghum bicolor	LOTUS Database	35616633
Suckleya suckleyana	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
Hexose monosaccharide
O-glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-1103 )

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	-0.77	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	143.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	30.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030704

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4475719

PDB ID

Not Available

ChEBI ID

16267

Good Scents ID

Not Available

References

General References

Kojima M, Poulton JE, Thayer SS, Conn EE: Tissue Distributions of Dhurrin and of Enzymes Involved in Its Metabolism in Leaves of Sorghum bicolor. Plant Physiol. 1979 Jun;63(6):1022-8. doi: 10.1104/pp.63.6.1022. [PubMed:16660850 ]
LOTUS database [Link]

Showing NP-Card for dhurrin (NP0249922)

MOL for NP0249922 (dhurrin)

3D MOL for NP0249922 (dhurrin)

3D SDF for NP0249922 (dhurrin)

3D-SDF for NP0249922 (dhurrin)

PDB for NP0249922 (dhurrin)

3D PDB for NP0249922 (dhurrin)

SMILES for NP0249922 (dhurrin)

INCHI for NP0249922 (dhurrin)

Structure for NP0249922 (dhurrin)

3D Structure for NP0249922 (dhurrin)