NP-MRD: Showing NP-Card for 2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid (NP0330926)

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Record Information

Version

1.0

Created at

2022-09-12 16:45:01 UTC

Updated at

2022-09-12 16:45:01 UTC

NP-MRD ID

NP0330926

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid

Description

Phosphoglucomutase belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Phosphoglucomutase is a very strong basic compound (based on its pKa). In humans, phosphoglucomutase is involved in the metabolic disorder called the sucrase-isomaltase deficiency pathway. This glucose 1-phosphate molecule is not itself a useful metabolic intermediate, but phosphoglucomutase catalyzes the conversion of this glucose 1-phosphate to glucose 6-phosphate (see below for the mechanism of this reaction). Outside of the human body, Phosphoglucomutase has been detected, but not quantified in, soy beans. This could make phosphoglucomutase a potential biomarker for the consumption of these foods. Substrate-velocity relationships and induced transport tests have revealed that the dephosphorylated enzyme then facilitates the transfer of a phosphoryl group from the glucose-1,6-bisphosphate intermediate to the enzyme, regenerating phosphorylated phosphoglucomutase and yielding glucose 6-phosphate (in the forward direction). The burial of the active site (including Ser-116, the critical residue on the enzyme that is phosphorylated and dephosphorylated) in the hydrophobic interior of the enzyme serves to exclude water from counterproductively hydrolyzing critical phosphoester bonds while still allowing the substrate to access the active site. If glycogenolysis is taking place in the liver, glucose 6-phosphate can be converted to glucose by the enzyme glucose 6-phosphatase; the glucose produced in the liver is then released to the bloodstream for use in other organs. Human muscle contains two phosphoglucomutases with nearly identical catalytic properties, PGM I and PGM II. 2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid is found in Daphnia magna, Homo sapiens and Mus musculus. PGM deficiency is an extremely rare condition that does not have a set of well-characterized physiological symptoms.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.8945    1.0950   -0.9797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9513    0.2289    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103   -0.9438    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -0.5068   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3345    0.2944   -1.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7339   -0.8574    0.7652 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6626   -0.5636    0.8341 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1182    0.4283   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    0.7526   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976    0.1551   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    0.7673   -0.4715 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    1.7307    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072    1.7412    0.6248 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -1.7711    0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.7493    0.9197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9039   -3.0017    0.6213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    2.0655   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5947    0.7564   -1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514    0.8143    1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9894   -0.1511    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -1.5529    0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241   -1.5291   -0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3082   -0.1155   -2.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180   -0.0610    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4854    1.3421   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.0309   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.6813   -1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1668    2.3855    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408    2.3582    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -3.4002   -0.3046 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
  4  6  2  0
  6  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
  7 14  1  0
 14 16  1  0
 14 15  2  0
 13  9  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652305221920072D          

 16 16  0  0  0  0            999 V2000
    1.9967    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    5.6518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  4  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330926

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC(O)=NC(CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)

> <INCHI_KEY>
CQOVPNPJLQNMDC-UHFFFAOYSA-N

> <FORMULA>
C9H14N4O3

> <MOLECULAR_WEIGHT>
226.2325

> <EXACT_MASS>
226.106590334

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.252921619588207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3-amino-1-hydroxypropylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-3.04

> <JCHEM_LOGP>
-4.93652586789241

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.206338085074754

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4160674025545408

> <JCHEM_PKA_STRONGEST_BASIC>
10.303835206622441

> <JCHEM_POLAR_SURFACE_AREA>
124.59000000000002

> <JCHEM_REFRACTIVITY>
56.0836

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-amino-1-hydroxypropylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       3.727   8.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.061   9.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.727   6.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.727   3.620   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.061  10.550   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.393   5.930   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       5.061   5.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.061   4.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.727   2.080   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1   10                                                       
CONECT    3    6    7                                                       
CONECT    4    6   11                                                       
CONECT    5   11   12                                                       
CONECT    6    3    4   12                                                  
CONECT    7    3    9   13                                                  
CONECT    8    1   13   14                                                  
CONECT    9    7   15   16                                                  
CONECT   10    2                                                            
CONECT   11    4    5                                                       
CONECT   12    5    6                                                       
CONECT   13    7    8                                                       
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
Ribonuclease, pancreatic	MeSH
RNase a	MeSH
Ribonuclease I	MeSH
Ribonuclease a	MeSH
Ribonuclease (pancreatic)	MeSH
RNase I	MeSH
Pancreatic rnase	MeSH
Pancreatic ribonuclease	MeSH
RNase, pancreatic	MeSH

Chemical Formula

C₉H₁₄N₄O₃

Average Mass

226.2325 Da

Monoisotopic Mass

226.10659 Da

IUPAC Name

2-[(3-amino-1-hydroxypropylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

2-[(3-amino-1-hydroxypropylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

NCCC(O)=NC(CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)

InChI Key

CQOVPNPJLQNMDC-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
Daphnia magna	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Primary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Primary aliphatic amine
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	-3	ALOGPS
logP	-4.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.08 m³·mol⁻¹	ChemAxon
Polarizability	22.25 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

FDB005612

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phosphoglucomutase

METLIN ID

Not Available

PubChem Compound

9369

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid (NP0330926)

MOL for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D MOL for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D SDF for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D-SDF for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

PDB for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D PDB for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

SMILES for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

INCHI for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

Structure for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)

3D Structure for NP0330926 (2-[(3-amino-1-hydroxypropylidene)amino]-3-(3h-imidazol-4-yl)propanoic acid)