NP-MRD: Showing NP-Card for (2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid (NP0251314)

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Record Information

Version

2.0

Created at

2022-09-07 14:28:29 UTC

Updated at

2022-09-07 14:28:29 UTC

NP-MRD ID

NP0251314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid

Description

(2S)-2-amino-6-{[(2E)-1-hydroxy-3-(1H-imidazol-5-yl)prop-2-en-1-ylidene]amino}hexanoic acid belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review very few articles have been published on (2S)-2-amino-6-{[(2E)-1-hydroxy-3-(1H-imidazol-5-yl)prop-2-en-1-ylidene]amino}hexanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072216282D          

 19 19  0  0  1  0            999 V2000
    3.3958   -2.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3958   -3.5940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6813   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668   -3.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379   -3.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -4.0065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -3.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8911   -2.7690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -4.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200   -5.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -6.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -6.2360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -5.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737   -4.9085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247   -3.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1102   -4.8315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 12 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCCCN=C(O)\C=C\C1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N4O3/c13-10(12(18)19)3-1-2-6-15-11(17)5-4-9-7-14-8-16-9/h4-5,7-8,10H,1-3,6,13H2,(H,14,16)(H,15,17)(H,18,19)/b5-4+/t10-/m0/s1

> <INCHI_KEY>
AKKJTDUPURYGPZ-YEZKRMTDSA-N

> <FORMULA>
C12H18N4O3

> <MOLECULAR_WEIGHT>
266.301

> <EXACT_MASS>
266.137890456

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.441269093772355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-{[(2E)-1-hydroxy-3-(1H-imidazol-5-yl)prop-2-en-1-ylidene]amino}hexanoic acid

> <JCHEM_LOGP>
-3.4620528292469297

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.502683316062182

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.136737239804801

> <JCHEM_PKA_STRONGEST_BASIC>
9.527468921611085

> <JCHEM_POLAR_SURFACE_AREA>
124.58999999999999

> <JCHEM_REFRACTIVITY>
71.02349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-6-{[(2E)-1-hydroxy-3-(3H-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0       6.339  -5.169   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.339  -6.709   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.005  -7.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.671  -6.709   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.338  -7.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.004  -6.709   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.330  -7.479   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.663  -6.709   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.663  -5.169   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.997  -7.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.997  -9.019   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.331  -9.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.492 -11.320   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -5.998 -11.641   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -6.768 -10.307   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -5.738  -9.162   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.672  -7.479   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.006  -6.709   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.672  -9.019   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-6-{[(2E)-1-hydroxy-3-(1H-imidazol-5-yl)prop-2-en-1-ylidene]amino}hexanoate	Generator

Chemical Formula

C₁₂H₁₈N₄O₃

Average Mass

266.3010 Da

Monoisotopic Mass

266.13789 Da

IUPAC Name

(2S)-2-amino-6-{[(2E)-1-hydroxy-3-(1H-imidazol-5-yl)prop-2-en-1-ylidene]amino}hexanoic acid

Traditional Name

(2S)-2-amino-6-{[(2E)-1-hydroxy-3-(3H-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCCN=C(O)\C=C\C1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C12H18N4O3/c13-10(12(18)19)3-1-2-6-15-11(17)5-4-9-7-14-8-16-9/h4-5,7-8,10H,1-3,6,13H2,(H,14,16)(H,15,17)(H,18,19)/b5-4+/t10-/m0/s1

InChI Key

AKKJTDUPURYGPZ-YEZKRMTDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Fatty acyl
Azole
Heteroaromatic compound
Imidazole
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
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	-3.5	ChemAxon
pKa (Strongest Acidic)	2.14	ChemAxon
pKa (Strongest Basic)	9.53	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	8	ChemAxon
Refractivity	71.02 m³·mol⁻¹	ChemAxon
Polarizability	28.44 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

Not Available

Chemspider ID

10480044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21777527

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid (NP0251314)

MOL for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

3D MOL for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

3D SDF for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

3D-SDF for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

PDB for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

3D PDB for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

SMILES for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

INCHI for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

Structure for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)

3D Structure for NP0251314 ((2s)-2-amino-6-{[(2e)-1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid)