NP-MRD: Showing NP-Card for (3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol (NP0207797)

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Record Information

Version

2.0

Created at

2022-09-05 04:33:09 UTC

Updated at

2022-09-05 04:33:09 UTC

NP-MRD ID

NP0207797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol

Description

Allosamizoline belongs to the class of organic compounds known as oxazolines. These are organic compounds containing 1,3-oxazoline, a five-membered ring with a nitrogen and an oxygen atoms at the 1- and 3-position, respectively. Additionally, it contains two double bonds. Allosamizoline is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.4668    1.6904    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    0.3198    0.2579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9504   -0.6694    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6873   -0.0304   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1769   -1.2071   -0.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924   -1.2406   -0.4946 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4692    0.1752   -0.9379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6988    0.8274   -0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.6206   -0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6185    1.4540   -1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878    1.6793   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668   -0.6917    0.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3138   -0.5628    1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -1.5232    0.6275 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4882   -2.8605    0.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    2.3936    0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877    2.0285    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0557    1.7655   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223   -1.6269    0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0066   -0.4515    0.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8406   -0.9252    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2780   -1.9745   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381    0.2441   -2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582    1.1493    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1366    2.4086   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    0.9145   -1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233    2.6607   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7583   -1.1037   -0.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0643   -1.1927    0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980   -1.0870    1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3286   -3.1842    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  6  1  0
  6  5  1  0
  5  4  2  0
  4  8  1  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  9 12  1  0
  7  6  1  0
 12 28  1  6
 13 29  1  0
 14 30  1  1
 15 31  1  0
  6 22  1  6
  7 23  1  6
  9 24  1  1
 10 25  1  0
 10 26  1  0
 11 27  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
M  END


  Mrv0541 05031423592D          

 20 21  0  0  1  0            999 V2000
    3.2917    0.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  2  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
    0.7846   -1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -2.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7216   -1.7348    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025    0.5203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -1.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0719    0.8219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.9049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  6  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  4  1  0  0  0  0
  8  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
  6 13  1  1  0  0  0
  7 14  1  6  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
  4 16  1  1  0  0  0
  5 17  1  6  0  0  0
  6 18  1  6  0  0  0
  7 19  1  1  0  0  0
  8 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0207797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O)[C@]([H])(O)[C@@]2([H])N=C(O[C@@]2([H])[C@]1([H])CO)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O4/c1-11(2)9-10-5-7(14)6(13)4(3-12)8(5)15-9/h4-8,12-14H,3H2,1-2H3/t4-,5-,6-,7-,8+/m1/s1

> <INCHI_KEY>
MKJAYSJDHSEFRI-PVFLNQBWSA-N

> <FORMULA>
C9H16N2O4

> <MOLECULAR_WEIGHT>
216.2343

> <EXACT_MASS>
216.11100701

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
21.7321021119486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazole-4,5-diol

> <ALOGPS_LOGP>
-1.56

> <JCHEM_LOGP>
-1.7314759463333336

> <ALOGPS_LOGS>
-0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.593104311205632

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.122265753582663

> <JCHEM_PKA_STRONGEST_BASIC>
6.81159964423901

> <JCHEM_POLAR_SURFACE_AREA>
85.52000000000001

> <JCHEM_REFRACTIVITY>
51.6807

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazole-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         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  C   UNK     0       0.000   0.000   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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+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
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    4   12                                                       
CONECT    4    3    6    8   16                                             
CONECT    5    7    8   10   17                                             
CONECT    6    4    7   13   18                                             
CONECT    7    5    6   14   19                                             
CONECT    8    4    5   15   20                                             
CONECT    9   10   11   15                                                  
CONECT   10    5    9                                                       
CONECT   11    1    2    9                                                  
CONECT   12    3                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8    9                                                       
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₆N₂O₄

Average Mass

216.2343 Da

Monoisotopic Mass

216.11101 Da

IUPAC Name

(3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazole-4,5-diol

Traditional Name

(3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazole-4,5-diol

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)[C@]([H])(O)[C@@]2([H])N=C(O[C@@]2([H])[C@]1([H])CO)N(C)C

InChI Identifier

InChI=1S/C9H16N2O4/c1-11(2)9-10-5-7(14)6(13)4(3-12)8(5)15-9/h4-8,12-14H,3H2,1-2H3/t4-,5-,6-,7-,8+/m1/s1

InChI Key

MKJAYSJDHSEFRI-PVFLNQBWSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolines. These are organic compounds containing 1,3-oxazoline, a five-membered ring with a nitrogen and an oxygen atoms at the 1- and 3-position, respectively. Additionally, it contains two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Oxazolines

Direct Parent

Oxazolines

Alternative Parents

Substituents

Cyclic alcohol
Oxazoline
Isourea
Secondary alcohol
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Hydrocarbon derivative
Primary alcohol
Organopnictogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-1.6	ALOGPS
logP	-1.7	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	13.12	ChemAxon
pKa (Strongest Basic)	6.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.52 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	51.68 m³·mol⁻¹	ChemAxon
Polarizability	21.73 Å³	ChemAxon
Number of Rings	2	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

DB04404

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

5287673

PDB ID

AMI

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol (NP0207797)

MOL for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

3D MOL for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

3D SDF for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

3D-SDF for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

PDB for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

3D PDB for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

SMILES for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

INCHI for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

Structure for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)

3D Structure for NP0207797 ((3ar,4r,5r,6r,6as)-2-(dimethylamino)-6-(hydroxymethyl)-3ah,4h,5h,6h,6ah-cyclopenta[d][1,3]oxazole-4,5-diol)