NP-MRD: Showing NP-Card for N-Acetyl-D-galactosamine 1-phosphate (NP0334760)

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Record Information

Version

2.0

Created at

2024-09-10 19:50:35 UTC

Updated at

2024-09-10 19:50:35 UTC

NP-MRD ID

NP0334760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-D-galactosamine 1-phosphate

Description

N-Acetyl-D-galactosamine 1-phosphate, also known as galnac-1-p, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-Acetyl-D-galactosamine 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220402D          

 19 19  0  0  1  0            999 V2000
   21.8282  -11.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8282  -12.2891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.1137  -11.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1137  -12.7016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.3993  -11.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.3993  -12.2891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.5427  -11.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5427  -12.7016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1137  -13.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6848  -12.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6848  -11.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9703  -11.4641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5427  -13.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2571  -13.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8282  -13.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5427   -9.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3677  -10.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7177  -10.2266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5427  -10.2266    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  6  0  0  0
  4  9  1  1  0  0  0
  6 10  1  1  0  0  0
  5 11  1  1  0  0  0
 12 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
  8 13  1  0  0  0  0
 18 19  2  0  0  0  0
 17 19  1  0  0  0  0
 16 19  1  0  0  0  0
  7 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6+,7-,8?/m1/s1

> <INCHI_KEY>
FZLJPEPAYPUMMR-KEWYIRBNSA-N

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.1877

> <EXACT_MASS>
301.056267627

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.464379632663622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.3441404429999997

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.238176832880029

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1819802553665197

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7889787416026043

> <JCHEM_POLAR_SURFACE_AREA>
165.77999999999997

> <JCHEM_REFRACTIVITY>
57.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic 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  C   UNK     0      40.746 -21.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      40.746 -22.940   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      39.412 -20.630   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      39.412 -23.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.079 -21.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.079 -22.940   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      42.080 -20.630   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      42.080 -23.710   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      39.412 -25.250   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      36.745 -23.710   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      36.745 -20.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      35.411 -21.400   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      42.080 -25.250   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      43.413 -26.020   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      40.746 -26.020   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      42.080 -17.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      43.620 -19.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      40.540 -19.090   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0      42.080 -19.090   0.000  0.00  0.00           P+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4    8                                                  
CONECT    3    1    5                                                       
CONECT    4    2    6    9                                                  
CONECT    5    3    6   11                                                  
CONECT    6    4    5   10                                                  
CONECT    7    1   19                                                       
CONECT    8    2   13                                                       
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    5   12                                                       
CONECT   12   11                                                            
CONECT   13   14   15    8                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   19                                                            
CONECT   17   19                                                            
CONECT   18   19                                                            
CONECT   19   18   17   16    7                                             
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-Acetamido-2-deoxy-1-O-phosphono-D-galactopyranose	ChEBI
N-Acetyl-D-galactosamine 1-phosphoric acid	Generator
N- Acetyl-alpha-D-galactosamine 1-phosphate	HMDB
N- Acetyl-alpha-delta-galactosamine 1-phosphate	HMDB
GalNAc-1-p	HMDB
N-Acetylgalactosamine-1-phosphate	HMDB

Chemical Formula

C₈H₁₆NO₉P

Average Mass

301.1877 Da

Monoisotopic Mass

301.05627 Da

IUPAC Name

{[(3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

[(3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)OC1OP(O)(O)=O

InChI Identifier

InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6+,7-,8?/m1/s1

InChI Key

FZLJPEPAYPUMMR-KEWYIRBNSA-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 n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Carbonyl group
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-galactosamine 1-phosphate (CHEBI:55404 )

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	ALOGPS
logP	-3.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-0.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.9 m³·mol⁻¹	ChemAxon
Polarizability	25.46 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

HMDB0006480

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023931

KNApSAcK ID

Not Available

Chemspider ID

17216370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2241575

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833661

PDB ID

Not Available

ChEBI ID

55404

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-Acetyl-D-galactosamine 1-phosphate (NP0334760)

MOL for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

3D MOL for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

3D SDF for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

3D-SDF for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

PDB for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

3D PDB for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

SMILES for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

INCHI for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

Structure for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)

3D Structure for NP0334760 (N-Acetyl-D-galactosamine 1-phosphate)