NP-MRD: Showing NP-Card for 2-(3-Carboxy-3-aminopropyl)-L-histidine (NP0091532)

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Record Information

Version

1.0

Created at

2022-05-11 18:40:38 UTC

Updated at

2022-05-11 18:40:38 UTC

NP-MRD ID

NP0091532

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-Carboxy-3-aminopropyl)-L-histidine

Description

2-(3-Carboxy-3-aminopropyl)-L-histidine, also known as 2-(3-amino-3-carboxypropyl)-L-histidine, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 2-(3-Carboxy-3-aminopropyl)-L-histidine is a very strong basic compound (based on its pKa). 2-(3-Carboxy-3-aminopropyl)-L-histidine exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.7833    2.0081    0.6574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7658    1.2284   -0.0288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8058    0.7608    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214   -0.0442    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -1.4092    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5473   -1.7478   -0.2302 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -0.6249   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5286   -0.6273   -1.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -0.7723    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405   -0.7809   -0.4447 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2146    0.4538   -1.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478   -0.9259    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230   -1.9391    1.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9235    0.0096    0.8241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5352    0.4203    0.0020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3435    0.0868   -0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5921   -0.1096   -0.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -0.8025   -1.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5240    3.0214    0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    1.8539    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854    1.8426   -0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.1515    1.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189    1.6405    1.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -2.0988    0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    0.3133   -1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077   -1.4466   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637    0.0831    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3610   -1.7240    0.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -1.6494   -1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739    1.2311   -0.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2103    0.4482   -1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9476    0.9327    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    1.4208   -0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162   -1.2044   -2.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 16  1  0
 16 18  1  0
 16 17  2  0
  4 15  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
 15  7  1  0
 11 30  1  0
 11 31  1  0
 10 29  1  6
  9 27  1  0
  9 28  1  0
  8 25  1  0
  8 26  1  0
  5 24  1  0
  3 22  1  0
  3 23  1  0
  2 21  1  6
  1 19  1  0
  1 20  1  0
 18 34  1  0
 15 33  1  0
 14 32  1  0
M  END


  Mrv0541 02241201492D          

 18 18  0  0  1  0            999 V2000
   13.7856   -6.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5309   -6.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0830   -5.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8280   -4.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3125   -3.9780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8280   -3.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434   -3.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0434   -4.3905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3760   -3.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6224   -3.4160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9549   -2.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0411   -2.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2013   -3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5361   -4.2367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5925   -6.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8472   -7.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1447   -6.3864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2334   -7.4405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1

> <INCHI_KEY>
CJCSNWWKPUXVRD-MLWJPKLSSA-N

> <FORMULA>
C10H16N4O4

> <MOLECULAR_WEIGHT>
256.2584

> <EXACT_MASS>
256.11715502

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
25.5437504836479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid

> <ALOGPS_LOGP>
-4.08

> <JCHEM_LOGP>
-6.493360252363875

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.232660542859342

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.629480153597954

> <JCHEM_PKA_STRONGEST_BASIC>
9.77576919184479

> <JCHEM_POLAR_SURFACE_AREA>
155.32

> <JCHEM_REFRACTIVITY>
61.1437

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      25.733 -12.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.258 -11.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.288 -10.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.812  -8.671   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      26.717  -7.426   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      25.812  -6.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.348  -6.656   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      24.348  -8.196   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      23.102  -5.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.695  -6.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.449  -5.471   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      20.610  -3.940   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      19.042  -6.097   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      21.534  -7.909   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      27.239 -13.065   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      27.715 -14.530   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      28.270 -11.921   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      24.702 -13.889   0.000  0.00  0.00           N+0
CONECT    1    2   15   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    4    7                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    1   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-(3-Amino-3-carboxypropyl)-L-histidine	HMDB
2-Amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoate	HMDB
2-Amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid	HMDB
2-(3-Carboxy-3-aminopropyl)-L-histidine	ChEBI

Chemical Formula

C₁₀H₁₆N₄O₄

Average Mass

256.2584 Da

Monoisotopic Mass

256.11716 Da

IUPAC Name

2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid

Traditional Name

2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

InChI Identifier

InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1

InChI Key

CJCSNWWKPUXVRD-MLWJPKLSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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

Histidine and derivatives

Alternative Parents

Substituents

Histidine or derivatives
Alpha-amino acid
L-alpha-amino acid
Imidazolyl carboxylic acid derivative
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17144 )
L-histidine derivative (CHEBI:17144 )

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	-4.1	ALOGPS
logP	-6.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.63	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	61.14 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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