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Showing NP-Card for Gyromitrin (NP0047795)

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Record Information
Version2.0
Created at2022-03-17 20:46:06 UTC
Updated at2022-03-17 20:46:06 UTC
NP-MRD IDNP0047795
Secondary Accession NumbersNone
Natural Product Identification
Common NameGyromitrin
DescriptionGyromitrin belongs to the class of organic compounds known as n-alkylated hydrazones. These are organonitrogen compounds containing a hydrazone group that is substituted with an alkyl group. They have the generic structure RNN=C(R')R\" (R= alkyl group; R',R\"= H or organyl group). Gyromitrin is a moderately basic compound (based on its pKa). Outside of the human body, Gyromitrin has been detected, but not quantified in, mushrooms. Gyromitrin is found in Gyromitra esculenta . This could make gyromitrin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047795 (Gyromitrin)


  Mrv0541 05061307282D          

  7  6  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
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3D MOL for NP0047795 (Gyromitrin)

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3D SDF for NP0047795 (Gyromitrin)

  Mrv0541 05061307282D          

  7  6  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=N/N(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3-

> <INCHI_KEY>
IMAGWKUTFZRWSB-HYXAFXHYSA-N

> <FORMULA>
C4H8N2O

> <MOLECULAR_WEIGHT>
100.1191

> <EXACT_MASS>
100.063662888

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.040915230312843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N'-[(1Z)-ethylidene]-N-methylformohydrazide

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.7837724643333334

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.98067511998142

> <JCHEM_PKA_STRONGEST_BASIC>
2.582069043801492

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
27.047500000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N'-[(1Z)-ethylidene]-N-methylformohydrazide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047795 (Gyromitrin)
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PDB for NP0047795 (Gyromitrin)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    6                                                            
CONECT    3    1    5                                                       
CONECT    4    6    7                                                       
CONECT    5    3    6                                                       
CONECT    6    2    4    5                                                  
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0047795 (Gyromitrin)
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SMILES for NP0047795 (Gyromitrin)
C\C=N/N(C)C=O
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INCHI for NP0047795 (Gyromitrin)
InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3-
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Synonyms
ValueSource
Acetaldehyde formylmethylhydrazoneHMDB
Acetaldehyde methylformylhydrazoneHMDB
Acetaldehyde N-formyl-N-methylhydrazoneHMDB
Acetaldehyde N-methyl-N-formylhydrazoneHMDB
Acetaldehyde N-methylformylhydrazoneHMDB
Acetaldehyde, N-formyl-N-methylhydrazoneHMDB
Acetaldehyde-N-formyl-N-methylhydrazoneHMDB
Acetaldehyde-N-methyl-N-formylhydrazoneHMDB
Acetylaldehyde-N-methyl-N-formylhydrazoneHMDB
Cetaldehyde methylformylhydrazoneHMDB
Ethylidene gyromitrinHMDB
Ethylidenemethyl-hydrazine carboxaldehydeHMDB
Ethylidenemethyl-hydrazine carboxyaldehydeHMDB
Ethylidenemethyl-hydrazinecarboxaldehydeHMDB
Ethylidenemethylhydrazinecarboxaldehyde, 9ciHMDB
Formic acid 2-ethylidene-1-methylhydrazideHMDB
Formic acid, 2-ethylidene-1-methylhydrazideHMDB
Formic acid, ethylidenemethylhydrazideHMDB
Hydrazinecarboxaldehyde, ethylidenemethyl- (9ci)HMDB
N'-ethylidene-N-formyl-N-methylhydrazineHMDB
N'-ethylidene-N-methylformic hydrazideHMDB
N'-ethylidene-N-methylformohydrazideHMDB
N'-[(1E)-ethylidene]-N-methylformic hydrazideHMDB
N'-[-ethylidene]-N-methylformic hydrazideHMDB
N-Methyl-N-formyl hydrazone OF acetaldehydeHMDB
N-Methyl-N-formylhydrazone acetaldehydeHMDB
Chemical FormulaC4H8N2O
Average Mass100.1191 Da
Monoisotopic Mass100.06366 Da
IUPAC NameN'-[(1Z)-ethylidene]-N-methylformohydrazide
Traditional NameN'-[(1Z)-ethylidene]-N-methylformohydrazide
CAS Registry Number16568-02-8
SMILES
C\C=N/N(C)C=O
InChI Identifier
InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3-
InChI KeyIMAGWKUTFZRWSB-HYXAFXHYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Gyromitra esculentaFungi
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-alkylated hydrazones. These are organonitrogen compounds containing a hydrazone group that is substituted with an alkyl group. They have the generic structure RNN=C(R')R\" (R= alkyl group; R',R\"= H or organyl group).
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassHydrazines and derivatives  
Direct ParentN-alkylated hydrazones  
Alternative Parents
Substituents
  • N-alkylated hydrazone
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.61ALOGPS
logP-0.78ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)19.98ChemAxon
pKa (Strongest Basic)2.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.05 m³·mol⁻¹ChemAxon
Polarizability10.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033952  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012167  
KNApSAcK IDC00001412  
Chemspider ID19957776  
KEGG Compound IDC08305  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGyromitrin  
METLIN IDNot Available
PubChem Compound5365327  
PDB IDNot Available
ChEBI ID5583  
Good Scents IDNot Available
References
General ReferencesNot Available