NP-MRD: Showing NP-Card for Acetylcarnosine (NP0339108)

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Record Information

Version

2.0

Created at

2024-09-11 19:43:23 UTC

Updated at

2024-09-11 19:43:23 UTC

NP-MRD ID

NP0339108

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetylcarnosine

Description

Acetylcarnosine 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. Acetylcarnosine is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 19 19  0  0  1  0            999 V2000
   12.3273  -20.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4988  -21.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8857  -22.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2835  -21.8892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8966  -21.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6812  -21.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2943  -21.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0789  -21.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1228  -20.2331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7358  -19.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5643  -18.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1774  -18.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0912  -17.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8449  -17.1660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3969  -17.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9844  -18.4936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5204  -19.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6920  -20.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1335  -19.3839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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 17  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  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
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339108

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NCCC(=O)N[C@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m1/s1

> <INCHI_KEY>
BKAYIFDRRZZKNF-SECBINFHSA-N

> <FORMULA>
C11H16N4O4

> <MOLECULAR_WEIGHT>
268.2691

> <EXACT_MASS>
268.11715502

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.10082441935205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
-3.212802230713907

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.85443438342254

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6061761262114427

> <JCHEM_PKA_STRONGEST_BASIC>
6.7509798518152

> <JCHEM_POLAR_SURFACE_AREA>
124.18

> <JCHEM_REFRACTIVITY>
65.00569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-(3-acetamidopropanamido)-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      23.011 -38.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.331 -40.384   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      22.187 -41.414   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      24.796 -40.860   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      25.940 -39.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.405 -40.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.549 -39.275   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.014 -39.751   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      28.229 -37.768   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      29.373 -36.738   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.053 -35.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.198 -34.201   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.037 -32.670   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      31.444 -32.043   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      32.474 -33.188   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      31.704 -34.521   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      30.838 -37.214   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      31.158 -38.720   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      31.983 -36.183   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15                                                       
CONECT   17   10   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
N-Acetylcarnosine	HMDB
(2R)-2-({1-hydroxy-3-[(1-hydroxyethylidene)amino]propylidene}amino)-3-(1H-imidazol-5-yl)propanoate	Generator

Chemical Formula

C₁₁H₁₆N₄O₄

Average Mass

268.2691 Da

Monoisotopic Mass

268.11716 Da

IUPAC Name

(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2R)-2-(3-acetamidopropanamido)-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NCCC(=O)N[C@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m1/s1

InChI Key

BKAYIFDRRZZKNF-SECBINFHSA-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 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
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Azole
Heteroaromatic compound
Imidazole
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
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	-0.93	ALOGPS
logP	-3.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.18 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.01 m³·mol⁻¹	ChemAxon
Polarizability	26.1 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

HMDB0012881

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029196

KNApSAcK ID

Not Available

Chemspider ID

8396518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetylcarnosine

METLIN ID

Not Available

PubChem Compound

10221026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acetylcarnosine (NP0339108)

MOL for NP0339108 (Acetylcarnosine)

3D MOL for NP0339108 (Acetylcarnosine)

3D SDF for NP0339108 (Acetylcarnosine)

3D-SDF for NP0339108 (Acetylcarnosine)

PDB for NP0339108 (Acetylcarnosine)

3D PDB for NP0339108 (Acetylcarnosine)

SMILES for NP0339108 (Acetylcarnosine)

INCHI for NP0339108 (Acetylcarnosine)

Structure for NP0339108 (Acetylcarnosine)

3D Structure for NP0339108 (Acetylcarnosine)