NP-MRD: Showing NP-Card for (2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol (NP0213232)

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Record Information

Version

2.0

Created at

2022-09-05 12:09:15 UTC

Updated at

2022-09-05 12:09:15 UTC

NP-MRD ID

NP0213232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol

Description

CHEMBL2442253 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,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol is found in Suregada glomerulata. Based on a literature review very few articles have been published on CHEMBL2442253.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.2503    1.8563   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708    0.7779   -0.3820 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1165    0.0794   -0.5666 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2070    0.8217    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4308    0.1718    0.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302   -1.3725   -0.2558 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8280   -2.1117   -1.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140   -1.7355    0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270   -1.2925    0.2950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5308   -2.0261   -0.8637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    0.1621    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7067    0.8542    1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    2.1897    1.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6719    2.4853   -1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0817    2.4902   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831    1.4183   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    0.1892   -1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    0.7627    1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847    1.8619   -0.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423    0.3625    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193   -1.7183    0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -3.0426   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260   -1.1614    1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0996   -2.8280    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -1.5446    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -1.5268   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0640    0.3750   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464    0.7585    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6641    0.3843    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132    2.3592    0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  6
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  1
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  1
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 13 30  1  0
M  END


  Mrv1652309052214092D          

 13 13  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   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   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  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
    0.0000    0.8250    0.0000 C   0  0  1  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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@@H](CO)[C@H](O)C[C@H](O)[C@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H17NO4/c1-9-5(3-10)7(12)2-8(13)6(9)4-11/h5-8,10-13H,2-4H2,1H3/t5-,6+,7+,8-

> <INCHI_KEY>
CDGKBGOAPNEEAH-SOSBWXJGSA-N

> <FORMULA>
C8H17NO4

> <MOLECULAR_WEIGHT>
191.227

> <EXACT_MASS>
191.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
19.900147695076537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,5R,6S)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol

> <JCHEM_LOGP>
-2.4427355066666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.586291133383366

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.036436225443516

> <JCHEM_PKA_STRONGEST_BASIC>
8.213514554338788

> <JCHEM_POLAR_SURFACE_AREA>
84.16000000000001

> <JCHEM_REFRACTIVITY>
46.7345

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,5R,6S)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₇NO₄

Average Mass

191.2270 Da

Monoisotopic Mass

191.11576 Da

IUPAC Name

(2R,3S,5R,6S)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol

Traditional Name

(2R,3S,5R,6S)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol

CAS Registry Number

Not Available

SMILES

CN1[C@@H](CO)[C@H](O)C[C@H](O)[C@H]1CO

InChI Identifier

InChI=1S/C8H17NO4/c1-9-5(3-10)7(12)2-8(13)6(9)4-11/h5-8,10-13H,2-4H2,1H3/t5-,6+,7+,8-

InChI Key

CDGKBGOAPNEEAH-SOSBWXJGSA-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
Suregada glomerulata	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
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Azacycle
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen 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	-2.4	ChemAxon
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	84.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.73 m³·mol⁻¹	ChemAxon
Polarizability	19.9 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

30838233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72204015

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol (NP0213232)

MOL for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

3D MOL for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

3D SDF for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

3D-SDF for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

PDB for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

3D PDB for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

SMILES for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

INCHI for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

Structure for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)

3D Structure for NP0213232 ((2r,3s,5r,6s)-2,6-bis(hydroxymethyl)-1-methylpiperidine-3,5-diol)