NP-MRD: Showing NP-Card for (2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid (NP0174448)

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Record Information

Version

2.0

Created at

2022-09-03 11:42:20 UTC

Updated at

2022-09-03 11:42:21 UTC

NP-MRD ID

NP0174448

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid

Description

(2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid is found in Agaricus bisporus.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.5583    0.7043    1.7007 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7622   -0.0394    0.4914 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5253   -0.0935   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3680   -0.7433    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.7689   -0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2522   -0.2926   -1.7422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -1.3316   -0.1614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629   -1.3632   -0.9945 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3891   -0.7720   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562   -0.1409    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7501    0.4326    0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8474    0.3985    0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1518    1.0119    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2222    2.3566    0.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6918   -0.2305   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -0.8023   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8835    0.5236   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2351    0.0261   -1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5675    1.6269    0.1557 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    0.4574    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769    0.5286    2.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0816   -1.0659    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305    0.9363   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.6476   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -0.2044    1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -1.7834    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168   -1.7377    0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963   -1.8240   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6887   -0.1162    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8644    0.9233    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9298    0.4307   -0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3063    0.9228    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3148    2.6498   -0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5610   -0.2605   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038   -1.2867   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5204    1.5754    0.4672 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  1  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
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 19 36  1  0
M  END

 
  Mrv1533006081517552D          
 
 19 19  0  0  1  0            999 V2000
   12.4414   -6.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1559   -5.7751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8703   -6.1876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5848   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2993   -6.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0138   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7283   -6.1876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4428   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1573   -6.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4428   -4.9501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7283   -7.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5848   -4.9503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7393   -5.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0247   -6.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0246   -7.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7267   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4412   -7.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3052   -7.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5923   -7.0231    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  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  1  0  0  0
  4 12  2  0  0  0  0
  1 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  1 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0174448

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCC(=O)NNC1=CC=C(CO)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1

> <INCHI_KEY>
SRSPQXBFDCGXIZ-JTQLQIEISA-N

> <FORMULA>
C12H17N3O4

> <MOLECULAR_WEIGHT>
267.285

> <EXACT_MASS>
267.121906039

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.270917527231113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{N'-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid

> <ALOGPS_LOGP>
-1.28

> <JCHEM_LOGP>
-2.666401775187285

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.184374850406527

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0123265829787615

> <JCHEM_PKA_STRONGEST_BASIC>
9.3119428326923

> <JCHEM_POLAR_SURFACE_AREA>
124.67999999999999

> <JCHEM_REFRACTIVITY>
69.6064

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
agaritine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      23.224 -11.550   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      24.558 -10.780   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      25.891 -11.550   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      27.225 -10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.559 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.892 -10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.226 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.560 -10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      33.894 -11.550   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      32.560  -9.240   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      31.226 -13.090   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      27.225  -9.241   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.913 -10.793   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.579 -11.563   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.579 -13.103   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.890 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.224 -13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.236 -13.878   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.906 -13.110   0.000  0.00  0.00           O+0
CONECT    1    2   13   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    4                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    1                                                       
CONECT   18   15   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-5-{2-[4-(hydroxymethyl)phenyl]hydrazino}-5-oxopentanoic acid	ChEBI
beta-N-[gamma-L(+)-Glutamyl]-4-hydroxymethylphenylhydrazine	ChEBI
L-Glutamic acid, 5-(2-(4-(hydroxymethyl)phenyl)hydrazide)	ChEBI
(2S)-2-Amino-5-{2-[4-(hydroxymethyl)phenyl]hydrazino}-5-oxopentanoate	Generator
b-N-[g-L(+)-Glutamyl]-4-hydroxymethylphenylhydrazine	Generator
Β-N-[γ-L(+)-glutamyl]-4-hydroxymethylphenylhydrazine	Generator
L-Glutamate, 5-(2-(4-(hydroxymethyl)phenyl)hydrazide)	Generator

Chemical Formula

C₁₂H₁₇N₃O₄

Average Mass

267.2850 Da

Monoisotopic Mass

267.12191 Da

IUPAC Name

(2S)-2-amino-4-{N'-[4-(hydroxymethyl)phenyl]hydrazinecarbonyl}butanoic acid

Traditional Name

agaritine

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)NNC1=CC=C(CO)C=C1)C(O)=O

InChI Identifier

InChI=1S/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1

InChI Key

SRSPQXBFDCGXIZ-JTQLQIEISA-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 bisporus	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
L-alpha-amino acid
Benzyl alcohol
Phenylhydrazine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid hydrazide
Carboxylic acid salt
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Primary amine
Primary alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Aromatic alcohol
Primary aliphatic amine
Organic zwitterion
Organic salt
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbohydrazide (CHEBI:15336 )
benzyl alcohols (CHEBI:15336 )
non-proteinogenic L-alpha-amino acid (CHEBI:15336 )
L-glutamic acid derivative (CHEBI:15336 )

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	-1.3	ALOGPS
logP	-2.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	124.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.61 m³·mol⁻¹	ChemAxon
Polarizability	27.27 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001525

Chemspider ID

Not Available

KEGG Compound ID

C01550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Agaritine

METLIN ID

Not Available

PubChem Compound

439516

PDB ID

Not Available

ChEBI ID

15336

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid (NP0174448)

MOL for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

3D MOL for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

3D SDF for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

3D-SDF for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

PDB for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

3D PDB for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

SMILES for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

INCHI for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

Structure for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)

3D Structure for NP0174448 ((2s)-2-amino-4-{[4-(hydroxymethyl)phenyl]-c-hydroxycarbonohydrazonoyl}butanoic acid)