NP-MRD: Showing NP-Card for [(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid (NP0262332)

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Record Information

Version

2.0

Created at

2022-09-08 05:04:53 UTC

Updated at

2022-09-08 05:04:53 UTC

NP-MRD ID

NP0262332

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid

Description

2-[(2-Amino-1-hydroxy-3-methylbutylidene)amino]-2-(4,5-dihydroxypiperidin-2-yl)acetic acid belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Based on a literature review very few articles have been published on 2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-2-(4,5-dihydroxypiperidin-2-yl)acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
    4.4094    1.4451   -0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9943    0.9224   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6921    1.2609    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.5830   -0.4502 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4921   -0.9339   -1.7802 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725   -1.2281   -0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117   -2.6058   -0.2295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396   -0.5785    0.2590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4696   -1.2638    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4758   -1.9250    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -1.8536    2.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -2.6187    2.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -0.4072    0.4617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8597    0.1466   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    0.9295   -1.0930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0920    0.0610   -1.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125    1.6211    0.1008 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0035    1.3856    0.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9960    1.2730    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787    0.7290    1.3367 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1386    0.6923   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137    2.3786   -0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5686    1.5419   -1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    1.3963   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    2.2121    1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    1.3247    1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    0.4374    1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8401   -0.9480    0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -0.5179   -2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294   -1.9732   -1.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7772   -2.9902   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -2.0780   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -3.5451    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -1.0086    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -0.7411   -1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    0.7723   -1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    1.6841   -1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852   -0.8118   -1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5376    2.7421   -0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0628    0.4708    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520    2.1566    2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382    0.5295    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736    0.4986    2.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
 20 13  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  1
  5 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  6
 13 34  1  1
 14 35  1  0
 14 36  1  0
 15 37  1  6
 16 38  1  0
 17 39  1  6
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 12 33  1  0
M  END


  Mrv1652309082207042D          

 20 20  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262332

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(N)C(O)=NC(C1CC(O)C(O)CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23N3O5/c1-5(2)9(13)11(18)15-10(12(19)20)6-3-7(16)8(17)4-14-6/h5-10,14,16-17H,3-4,13H2,1-2H3,(H,15,18)(H,19,20)

> <INCHI_KEY>
QSPWYGGTCUYMRY-UHFFFAOYSA-N

> <FORMULA>
C12H23N3O5

> <MOLECULAR_WEIGHT>
289.332

> <EXACT_MASS>
289.163770853

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.47798441748576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-2-(4,5-dihydroxypiperidin-2-yl)acetic acid

> <JCHEM_LOGP>
-6.174625571372479

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.5104723710792887

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7688457964565387

> <JCHEM_PKA_STRONGEST_BASIC>
9.722274311909997

> <JCHEM_POLAR_SURFACE_AREA>
148.4

> <JCHEM_REFRACTIVITY>
69.7794

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.667   6.160   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-[(2-Amino-1-hydroxy-3-methylbutylidene)amino]-2-(4,5-dihydroxypiperidin-2-yl)acetate	Generator

Chemical Formula

C₁₂H₂₃N₃O₅

Average Mass

289.3320 Da

Monoisotopic Mass

289.16377 Da

IUPAC Name

2-[(2-amino-1-hydroxy-3-methylbutylidene)amino]-2-(4,5-dihydroxypiperidin-2-yl)acetic acid

Traditional Name

[(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(N)C(O)=NC(C1CC(O)C(O)CN1)C(O)=O

InChI Identifier

InChI=1S/C12H23N3O5/c1-5(2)9(13)11(18)15-10(12(19)20)6-3-7(16)8(17)4-14-6/h5-10,14,16-17H,3-4,13H2,1-2H3,(H,15,18)(H,19,20)

InChI Key

QSPWYGGTCUYMRY-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Piperidine
Amino acid
Secondary alcohol
Amino acid or derivatives
1,2-diol
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
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	-6.2	ChemAxon
pKa (Strongest Acidic)	2.77	ChemAxon
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.78 m³·mol⁻¹	ChemAxon
Polarizability	29.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

163061614

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-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid (NP0262332)

MOL for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

3D MOL for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

3D SDF for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

3D-SDF for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

PDB for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

3D PDB for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

SMILES for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

INCHI for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

Structure for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)

3D Structure for NP0262332 ([(2-amino-1-hydroxy-3-methylbutylidene)amino](4,5-dihydroxypiperidin-2-yl)acetic acid)