NP-MRD: Showing NP-Card for 2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid (NP0281662)

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Record Information

Version

2.0

Created at

2022-09-09 08:08:46 UTC

Updated at

2022-09-09 08:08:46 UTC

NP-MRD ID

NP0281662

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid

Description

Oxypinnatanine 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. Oxypinnatanine is a very strong basic compound (based on its pKa). Outside of the human body, Oxypinnatanine has been detected, but not quantified in, root vegetables. 2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid is found in Hemerocallis fulva. This could make oxypinnatanine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061304462D          

 18 18  0  0  0  0            999 V2000
    8.0414    4.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289    5.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779    4.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609    3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894    3.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634    3.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923    3.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068    4.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357    4.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    4.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634    2.9519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213    3.7769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4456    2.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068    5.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344    3.7769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    5.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8220    5.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  2  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  4  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 17 10  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281662

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC(O)C(\O)=N\C1OCC=C1CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O6/c11-6(10(16)17)3-7(14)8(15)12-9-5(4-13)1-2-18-9/h1,6-7,9,13-14H,2-4,11H2,(H,12,15)(H,16,17)

> <INCHI_KEY>
FKPGGSOHTXQOGP-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O6

> <MOLECULAR_WEIGHT>
260.2438

> <EXACT_MASS>
260.100836254

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
24.676276447364106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-hydroxy-4-[(Z)-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-3.07

> <JCHEM_LOGP>
-4.3301403184756015

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.254688974655627

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.815938721946881

> <JCHEM_PKA_STRONGEST_BASIC>
9.160835701170967

> <JCHEM_POLAR_SURFACE_AREA>
145.6

> <JCHEM_REFRACTIVITY>
60.16430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-hydroxy-4-[(Z)-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      15.011   8.338   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.241   9.672   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.239   7.820   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.300   5.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.980   7.194   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.905   7.050   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.572   7.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.906   7.820   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.573   7.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.571   7.820   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.905   5.510   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      11.240   7.050   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      15.765   5.212   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.572   5.510   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.906   9.360   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.238   7.050   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.571   9.360   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.734   9.352   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1   18                                                       
CONECT    3    6    7                                                       
CONECT    4    5   13                                                       
CONECT    5    1    4    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    3    8   14                                                  
CONECT    8    7   12   15                                                  
CONECT    9    5   12   18                                                  
CONECT   10    6   16   17                                                  
CONECT   11    6                                                            
CONECT   12    8    9                                                       
CONECT   13    4                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
N-[2,5-Dihydro-3-(hydroxymethyl)-2-furanyl]-4-hydroxyglutamine, 9ci	HMDB
2-Amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl}butanoate	Generator

Chemical Formula

C₁₀H₁₆N₂O₆

Average Mass

260.2438 Da

Monoisotopic Mass

260.10084 Da

IUPAC Name

2-amino-4-hydroxy-4-[(Z)-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

2-amino-4-hydroxy-4-[(Z)-[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-C-hydroxycarbonimidoyl]butanoic acid

CAS Registry Number

Not Available

SMILES

NC(CC(O)C(\O)=N\C1OCC=C1CO)C(O)=O

InChI Identifier

InChI=1S/C10H16N2O6/c11-6(10(16)17)3-7(14)8(15)12-9-5(4-13)1-2-18-9/h1,6-7,9,13-14H,2-4,11H2,(H,12,15)(H,16,17)

InChI Key

FKPGGSOHTXQOGP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hemerocallis fulva	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
Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Fatty amide
Fatty acyl
N-acyl-amine
1,3-aminoalcohol
Dihydrofuran
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary aliphatic amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Primary amine
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-3.1	ALOGPS
logP	-4.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.16 m³·mol⁻¹	ChemAxon
Polarizability	24.68 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

HMDB0029403

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000492

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14779021

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-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid (NP0281662)

MOL for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

3D MOL for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

3D SDF for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

3D-SDF for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

PDB for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

3D PDB for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

SMILES for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

INCHI for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

Structure for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)

3D Structure for NP0281662 (2-amino-4-hydroxy-4-{[3-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-c-hydroxycarbonimidoyl}butanoic acid)