NP-MRD: Showing NP-Card for 2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid (NP0249040)

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Record Information

Version

2.0

Created at

2022-09-07 11:29:39 UTC

Updated at

2022-09-07 11:29:39 UTC

NP-MRD ID

NP0249040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid

Description

Agaritinal belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid is found in Agaricus campestris. Agaritinal is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.3853    0.3871   -1.1610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    0.6356    0.1446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3616    0.5148    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842   -0.8552   -0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182   -1.0190   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3325   -0.0792    0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1180   -2.2829   -0.3830 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -2.5153   -0.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -1.4369   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.0009    1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6630    0.0327    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    0.6688    0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283    1.7581    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6172    2.3520   -0.7540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8052    0.2513   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -0.7869   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2372    2.0146    0.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674    2.4264    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9806    2.8425   -0.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224    0.7043   -1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9012   -0.4993   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3034   -0.1015    0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779    1.2791   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0199    0.7302    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -1.1815   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071   -1.6200    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905   -3.0971   -0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -3.4981   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807   -1.4830    1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875    0.3908    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4310    2.0843    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159    0.7495   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6248   -1.1043   -2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508    2.7391   -1.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  2  0
  2 17  1  0
 17 19  1  0
 17 18  2  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 19 34  1  0
M  END


  Mrv0541 09121202162D          

 19 19  0  0  0  0            999 V2000
    0.3708   -2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -2.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732   -0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8557    0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    1.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    2.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    0.8246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2884    1.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    0.4946    0.0000 O   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  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  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  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(=O)NNC1=CC=C(C=O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,7,10,14H,5-6,13H2,(H,15,17)(H,18,19)

> <INCHI_KEY>
OLPOUQMVOMXOGV-UHFFFAOYSA-N

> <FORMULA>
C12H15N3O4

> <MOLECULAR_WEIGHT>
265.2652

> <EXACT_MASS>
265.106255983

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.467208402764335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[N'-(4-formylphenyl)hydrazinecarbonyl]butanoic acid

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-2.1866470740049695

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.267076927335932

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8628078247650501

> <JCHEM_PKA_STRONGEST_BASIC>
9.311963611956147

> <JCHEM_POLAR_SURFACE_AREA>
121.52000000000001

> <JCHEM_REFRACTIVITY>
69.3745

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[N'-(4-formylphenyl)hydrazinecarbonyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-12         0                                  
HETATM    1  C   UNK     0       0.692  -4.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.924  -3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.924  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.538  -1.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.846  -1.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.692  -3.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.078  -4.003   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.078  -5.543   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.310  -0.769   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.464   0.769   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -3.464   3.233   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.078   4.003   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.924   5.543   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -1.308   1.539   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.846   3.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.538   3.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.924   3.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.232   1.539   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.846   0.923   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10                                                       
CONECT   10    9   18                                                       
CONECT   11   12                                                            
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   12   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   10   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
N2-(g-Glutamyl)-4-formylphenylhydrazine	HMDB
2-Amino-4-[(4-formylphenyl)-C-hydroxycarbonohydrazonoyl]butanoate	Generator

Chemical Formula

C₁₂H₁₅N₃O₄

Average Mass

265.2652 Da

Monoisotopic Mass

265.10626 Da

IUPAC Name

2-amino-4-[N'-(4-formylphenyl)hydrazinecarbonyl]butanoic acid

Traditional Name

2-amino-4-[N'-(4-formylphenyl)hydrazinecarbonyl]butanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCC(=O)NNC1=CC=C(C=O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C12H15N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,7,10,14H,5-6,13H2,(H,15,17)(H,18,19)

InChI Key

OLPOUQMVOMXOGV-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
Agaricus campestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
Benzaldehyde
Benzoyl
Phenylhydrazine
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid hydrazide
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	-0.33	ALOGPS
logP	-2.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.37 m³·mol⁻¹	ChemAxon
Polarizability	26.47 Å³	ChemAxon
Number of Rings	1	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

HMDB0040694

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020496

KNApSAcK ID

Not Available

Chemspider ID

8420081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10244594

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid (NP0249040)

MOL for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

3D MOL for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

3D SDF for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

3D-SDF for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

PDB for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

3D PDB for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

SMILES for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

INCHI for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

Structure for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)

3D Structure for NP0249040 (2-amino-4-[(4-formylphenyl)-c-hydroxycarbonohydrazonoyl]butanoic acid)