NP-MRD: Showing NP-Card for n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid (NP0218989)

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Record Information

Version

2.0

Created at

2022-09-05 19:49:44 UTC

Updated at

2022-09-05 19:49:44 UTC

NP-MRD ID

NP0218989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid

Description

Mycotoxin T 2 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. Mycotoxin T 2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mycotoxin T 2 has been detected, but not quantified in, a few different foods, such as fats and oils, green vegetables, and herbs and spices. This could make mycotoxin T 2 a potential biomarker for the consumption of these foods. n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid is found in Moringa oleifera. T-2 mycotoxin is able to inhibit DNA and RNA synthesis in vivo and in vitro and can induce apoptosis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210072D          

 24 25  0  0  0  0            999 V2000
   -2.1579    1.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    0.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    1.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    1.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -0.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    2.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    3.0832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    2.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280    3.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0178    1.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436    2.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579    3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280   -1.8447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991   -1.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991   -1.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -0.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138    0.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -0.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147   -2.2576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0138   -3.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)NCC1=CC=C(OC2OC(C)C(O)C(O)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO7/c1-3-22-16(21)17-8-10-4-6-11(7-5-10)24-15-14(20)13(19)12(18)9(2)23-15/h4-7,9,12-15,18-20H,3,8H2,1-2H3,(H,17,21)

> <INCHI_KEY>
UNNZZQOFLFJJJZ-UHFFFAOYSA-N

> <FORMULA>
C16H23NO7

> <MOLECULAR_WEIGHT>
341.3563

> <EXACT_MASS>
341.147452095

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.42666837963944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl N-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)carbamate

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.3692364973333329

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.20941045192837

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20621820520545

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003585840474

> <JCHEM_POLAR_SURFACE_AREA>
117.48000000000002

> <JCHEM_REFRACTIVITY>
82.929

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl N-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)carbamate

> <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  C   UNK     0      -4.028   2.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.028   1.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.695   0.410   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.364   1.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.364   2.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.695   3.490   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.695  -1.131   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.695   5.031   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.333   5.755   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.002   4.980   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.359   5.704   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.033   3.438   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.695   4.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.028   5.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.359  -1.902   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.359  -3.443   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.026  -4.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.305  -3.443   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.305  -1.902   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.026  -1.134   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.026   0.407   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.641  -1.131   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.641  -4.214   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.026  -5.755   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3   15                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    7   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   15   19   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   18                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
N-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidate	Generator

Chemical Formula

C₁₆H₂₃NO₇

Average Mass

341.3563 Da

Monoisotopic Mass

341.14745 Da

IUPAC Name

ethyl N-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)carbamate

Traditional Name

ethyl N-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)carbamate

CAS Registry Number

Not Available

SMILES

CCOC(=O)NCC1=CC=C(OC2OC(C)C(O)C(O)C2O)C=C1

InChI Identifier

InChI=1S/C16H23NO7/c1-3-22-16(21)17-8-10-4-6-11(7-5-10)24-15-14(20)13(19)12(18)9(2)23-15/h4-7,9,12-15,18-20H,3,8H2,1-2H3,(H,17,21)

InChI Key

UNNZZQOFLFJJJZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Moringa oleifera	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
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Carbamic acid ester
Carbonic acid derivative
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Organonitrogen compound
Organic nitrogen compound
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	0.35	ALOGPS
logP	0.37	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.48 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.93 m³·mol⁻¹	ChemAxon
Polarizability	35.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032864

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010842

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

T-2 mycotoxin

METLIN ID

Not Available

PubChem Compound

131751337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid (NP0218989)

MOL for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

3D MOL for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

3D SDF for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

3D-SDF for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

PDB for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

3D PDB for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

SMILES for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

INCHI for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

Structure for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)

3D Structure for NP0218989 (n-({4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}methyl)ethoxycarboximidic acid)