NP-MRD: Showing NP-Card for Homoanserine (NP0087406)

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Record Information

Version

2.0

Created at

2022-05-11 16:48:49 UTC

Updated at

2022-05-11 16:48:49 UTC

NP-MRD ID

NP0087406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homoanserine

Description

Homoanserine 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. Homoanserine was first documented in 1967 (PMID: 6078589). Homoanserine is a very strong basic compound (based on its pKa) (PMID: 3780724).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -4.4950    1.4691    0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4623    0.5787    1.1492 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817    0.0409    2.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052   -0.7323    2.5544 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -0.6550    1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    0.1517    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    0.5753   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7794    0.0797   -1.4552 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4365    0.4193   -0.8053 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -0.5674   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1800   -1.7583   -0.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6903   -0.2624    0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -1.5055    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8098   -1.1039    1.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.5212    2.3229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395    0.6568   -2.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650    1.3028   -3.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795    0.5052   -3.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2601    0.8864    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9533    2.0167    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873    2.2122   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2568    0.1893    3.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -1.1691    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773    0.2545   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.6871   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228   -1.0416   -1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    1.4014   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    0.2310    1.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3078    0.4420   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725   -2.1649    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -2.0279   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3871   -0.3825    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4163   -2.0355    1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951    0.5200    2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401   -0.9491    2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    1.2563   -4.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 18  1  0
 16 17  2  0
  6  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
  9 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
M  END


  Mrv0541 02231220282D          

 18 18  0  0  1  0            999 V2000
   11.9479  -10.2137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8616   -9.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6153   -9.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1674   -9.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7548  -10.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3348  -10.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0904  -11.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9109  -11.2251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3958  -10.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2464  -11.9788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0669  -12.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4026  -12.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5518  -11.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3724  -11.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8572  -10.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6777  -10.9026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0602   -9.8040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2163  -10.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
  8 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  2  0  0  0  0
 18  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC=C1C[C@H](NC(=O)CCCN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N4O3/c1-15-7-13-6-8(15)5-9(11(17)18)14-10(16)3-2-4-12/h6-7,9H,2-5,12H2,1H3,(H,14,16)(H,17,18)/t9-/m0/s1

> <INCHI_KEY>
HXBKNURIXGGFCX-VIFPVBQESA-N

> <FORMULA>
C11H18N4O3

> <MOLECULAR_WEIGHT>
254.2856

> <EXACT_MASS>
254.137890462

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.236386430304282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(4-aminobutanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-3.979975149409272

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.868423390861945

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5181907166805684

> <JCHEM_PKA_STRONGEST_BASIC>
9.99104393457487

> <JCHEM_POLAR_SURFACE_AREA>
110.24

> <JCHEM_REFRACTIVITY>
65.21360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(4-aminobutanamido)-3-(3-methylimidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      22.303 -19.066   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      22.142 -17.534   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      23.549 -16.907   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      24.579 -18.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.809 -19.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.158 -20.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.435 -20.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.967 -20.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.872 -19.708   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      26.593 -22.360   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      28.125 -22.521   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      28.751 -23.928   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      29.030 -21.275   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.562 -21.436   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.467 -20.191   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      32.998 -20.352   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      26.246 -18.301   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      28.404 -19.869   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    7                                                  
CONECT    6    1                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   17   18                                                  
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
L-N-(4-Aminobutyryl)-3-methyl-histidine	HMDB
N-(4-Amino-1-oxobutyl)-3-methyl-L-histidine	HMDB
N-(4-Aminobutyryl)-1-methyl-imidazole-5-alanine	HMDB
(2S)-2-[(4-Amino-1-hydroxybutylidene)amino]-3-(1-methyl-1H-imidazol-5-yl)propanoate	HMDB

Chemical Formula

C₁₁H₁₈N₄O₃

Average Mass

254.2856 Da

Monoisotopic Mass

254.13789 Da

IUPAC Name

(2S)-2-(4-aminobutanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-(4-aminobutanamido)-3-(3-methylimidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CN1C=NC=C1C[C@H](NC(=O)CCCN)C(O)=O

InChI Identifier

InChI=1S/C11H18N4O3/c1-15-7-13-6-8(15)5-9(11(17)18)14-10(16)3-2-4-12/h6-7,9H,2-5,12H2,1H3,(H,14,16)(H,17,18)/t9-/m0/s1

InChI Key

HXBKNURIXGGFCX-VIFPVBQESA-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 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
N-acyl-l-alpha-amino acid
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Fatty amide
N-acyl-amine
N-substituted imidazole
Fatty acyl
Heteroaromatic compound
Azole
Imidazole
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Amino acid or derivatives
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic oxide
Primary aliphatic amine
Carbonyl group
Primary amine
Hydrocarbon derivative
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	-2.8	ALOGPS
logP	-4	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	9.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.24 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.21 m³·mol⁻¹	ChemAxon
Polarizability	26.24 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

HMDB0005767

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023757

KNApSAcK ID

Not Available

Chemspider ID

17216339

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20849429

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kunze N, Kleinkauf H, Bauer K: Characterization of two carnosine-degrading enzymes from rat brain. Partial purification and characterization of a carnosinase and a beta-alanyl-arginine hydrolase. Eur J Biochem. 1986 Nov 3;160(3):605-13. doi: 10.1111/j.1432-1033.1986.tb10081.x. [PubMed:3780724 ]
Nakajima T, Wolfgram F, Clark WG: The isolation of homoanserine from bovine brain. J Neurochem. 1967 Dec;14(12):1107-12. doi: 10.1111/j.1471-4159.1967.tb06156.x. [PubMed:6078589 ]

Showing NP-Card for Homoanserine (NP0087406)

MOL for NP0087406 (Homoanserine)

3D MOL for NP0087406 (Homoanserine)

3D SDF for NP0087406 (Homoanserine)

3D-SDF for NP0087406 (Homoanserine)

PDB for NP0087406 (Homoanserine)

3D PDB for NP0087406 (Homoanserine)

SMILES for NP0087406 (Homoanserine)

INCHI for NP0087406 (Homoanserine)

Structure for NP0087406 (Homoanserine)

3D Structure for NP0087406 (Homoanserine)