NP-MRD: Showing NP-Card for D(+)-Glucosamine Hydrochloride (NP0331790)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-09-05 20:04:49 UTC

Updated at

2024-09-03 04:16:56 UTC

NP-MRD ID

NP0331790

Natural Product DOI

https://doi.org/10.57994/0866

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D(+)-Glucosamine Hydrochloride

Description

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004221604002D          

 18 17  0  0  1  0            999 V2000
    1.5550    0.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    0.1941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5884   -0.6309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1261    0.6066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5884    0.1941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1261   -1.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -1.0434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550    1.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261    1.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029    0.6066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261   -1.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -0.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    1.0191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -0.2184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884    1.0191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1261   -0.2184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5884   -1.4559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  3  7  1  6  0  0  0
  8  1  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  6  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  1  0  0  0  0
  2 14  1  6  0  0  0
  3 15  1  1  0  0  0
  4 16  1  1  0  0  0
  5 17  1  6  0  0  0
 18  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Cl.[H][C@]1(N)C([H])(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1

> <INCHI_KEY>
QKPLRMLTKYXDST-NSEZLWDYSA-N

> <FORMULA>
C6H14ClNO5

> <MOLECULAR_WEIGHT>
215.63

> <EXACT_MASS>
215.0560503

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
16.48421020530823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

> <ALOGPS_LOGP>
-2.73

> <JCHEM_LOGP>
-3.0394210146666665

> <ALOGPS_LOGS>
0.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.974072372694078

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.726975176724002

> <JCHEM_PKA_STRONGEST_BASIC>
8.229727434444008

> <JCHEM_POLAR_SURFACE_AREA>
116.17000000000002

> <JCHEM_REFRACTIVITY>
37.5809

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucosamine hydrochloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.903   1.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.569   0.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.098  -1.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.235   1.132   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.098   0.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.235  -1.948   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.432  -1.948   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.903   2.672   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.235   2.672   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.432   1.132   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.235  -3.488   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.569  -1.178   0.000  0.00  0.00           O+0
HETATM   13 Cl   UNK     0       6.643   0.000   0.000  0.00  0.00          Cl+0
HETATM   14  H   UNK     0       1.569   1.902   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.432  -0.408   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.098   1.902   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.235  -0.408   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.098  -2.718   0.000  0.00  0.00           H+0
CONECT    1    2    8                                                       
CONECT    2    1    4   12   14                                             
CONECT    3    5    6    7   15                                             
CONECT    4    2    5    9   16                                             
CONECT    5    3    4   10   17                                             
CONECT    6    3   11   12   18                                             
CONECT    7    3                                                            
CONECT    8    1                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    2    6                                                       
CONECT   14    2                                                            
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆H₁₄ClNO₅

Average Mass

215.6300 Da

Monoisotopic Mass

215.05605 Da

IUPAC Name

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Traditional Name

glucosamine hydrochloride

CAS Registry Number

Not Available

SMILES

Cl.[H][C@]1(N)C([H])(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1

InChI Key

QKPLRMLTKYXDST-NSEZLWDYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-05	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, D₂O, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Amino saccharide
Oxane
1,2-aminoalcohol
Hemiacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Primary alcohol
Primary amine
Hydrochloride
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-2.7	ALOGPS
logP	-3	ChemAxon
logS	0.49	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.58 m³·mol⁻¹	ChemAxon
Polarizability	16.48 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2723635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for D(+)-Glucosamine Hydrochloride (NP0331790)

MOL for NP0331790 (D(+)-Glucosamine Hydrochloride)

3D MOL for NP0331790 (D(+)-Glucosamine Hydrochloride)

3D SDF for NP0331790 (D(+)-Glucosamine Hydrochloride)

3D-SDF for NP0331790 (D(+)-Glucosamine Hydrochloride)

PDB for NP0331790 (D(+)-Glucosamine Hydrochloride)

3D PDB for NP0331790 (D(+)-Glucosamine Hydrochloride)

SMILES for NP0331790 (D(+)-Glucosamine Hydrochloride)

INCHI for NP0331790 (D(+)-Glucosamine Hydrochloride)

Structure for NP0331790 (D(+)-Glucosamine Hydrochloride)

3D Structure for NP0331790 (D(+)-Glucosamine Hydrochloride)