NP-MRD: Showing NP-Card for (2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol (NP0155062)

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Record Information

Version

2.0

Created at

2022-09-02 12:03:52 UTC

Updated at

2022-09-02 12:03:52 UTC

NP-MRD ID

NP0155062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

Description

Alpha-Homonojirimycin belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. (2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol is found in Hyacinthus orientalis, Lonchocarpus heptaphyllus and Omphalea diandra. Alpha-Homonojirimycin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09041212562D          

 18 18  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.6002    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.7752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  4  2  1  6  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  6  0  0  0
 13  7  1  0  0  0  0
  3 14  1  6  0  0  0
  4 15  1  1  0  0  0
  5 16  1  1  0  0  0
  6 17  1  1  0  0  0
 18  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155062

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H15NO5/c9-1-3-5(11)7(13)6(12)4(2-10)8-3/h3-13H,1-2H2/t3-,4-,5-,6+,7?/m1/s1

> <INCHI_KEY>
CLVUFWXGNIFGNC-QTSLKERKSA-N

> <FORMULA>
C7H15NO5

> <MOLECULAR_WEIGHT>
193.1977

> <EXACT_MASS>
193.095022595

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
18.54844397131349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-3.516078125

> <ALOGPS_LOGS>
0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.866726858780108

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.839470828340176

> <JCHEM_PKA_STRONGEST_BASIC>
7.60127730030343

> <JCHEM_POLAR_SURFACE_AREA>
113.18

> <JCHEM_REFRACTIVITY>
42.536899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.02e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    9                                                       
CONECT    2    4   10                                                       
CONECT    3    1    5    8   14                                             
CONECT    4    2    6    8   15                                             
CONECT    5    3    7   11   16                                             
CONECT    6    4    7   12   17                                             
CONECT    7    5    6   13   18                                             
CONECT    8    3    4                                                       
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    5                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
a-Homonojirimycin	Generator
Α-homonojirimycin	Generator
Homonojirimycin	MeSH
Homo-nojirimycin	MeSH

Chemical Formula

C₇H₁₅NO₅

Average Mass

193.1977 Da

Monoisotopic Mass

193.09502 Da

IUPAC Name

(2R,3R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

Traditional Name

(2R,3R,5S,6R)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H15NO5/c9-1-3-5(11)7(13)6(12)4(2-10)8-3/h3-13H,1-2H2/t3-,4-,5-,6+,7?/m1/s1

InChI Key

CLVUFWXGNIFGNC-QTSLKERKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Hyacinthus orientalis	LOTUS Database	35616633
Lonchocarpus latifolius	LOTUS Database	35616633
Omphalea diandra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Polyol
Secondary amine
Azacycle
Primary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Hydrocarbon derivative
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	-2.3	ALOGPS
logP	-3.5	ChemAxon
logS	0.19	ALOGPS
pKa (Strongest Acidic)	12.84	ChemAxon
pKa (Strongest Basic)	7.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	113.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.54 m³·mol⁻¹	ChemAxon
Polarizability	18.55 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

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

159496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol (NP0155062)

MOL for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

3D MOL for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

3D SDF for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

3D-SDF for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

PDB for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

3D PDB for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

SMILES for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

INCHI for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

Structure for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)

3D Structure for NP0155062 ((2r,3r,5s,6r)-2,6-bis(hydroxymethyl)piperidine-3,4,5-triol)