NP-MRD: Showing NP-Card for [(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate (NP0165047)

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Record Information

Version

2.0

Created at

2022-09-03 00:03:48 UTC

Updated at

2022-09-03 00:03:48 UTC

NP-MRD ID

NP0165047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate

Description

Gabosine K belongs to the class of organic compounds known as cyclitols and derivatives. Cyclitols and derivatives are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms. These of also include derivatives where the hydrogen atom of one or more of the hydroxyl groups is replaced with another atom. [(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate was first documented in 2013 (PMID: 23879653). Based on a literature review very few articles have been published on Gabosine K (PMID: 28276688).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    4.2516   -0.9308   -0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149   -0.4489   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4134   -1.2096    0.7158 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5445    0.8124   -0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4109    1.3561    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350    0.7283   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -0.3090   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.8082   -1.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9986    0.0075   -2.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945   -0.8719    0.1247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5372   -0.2825   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -0.0006    1.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6854   -0.7283    1.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742    1.2259    0.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9745    2.2851    1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946   -1.2002    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326   -0.1410   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495   -1.8422   -1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989    1.3669    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424    2.4258   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8029   -0.7560   -1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274   -1.8588   -1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9889    0.0001   -2.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4728   -1.9078    0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652   -0.3073    0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4758    0.2590    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4148   -1.4804    1.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778    1.5392   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4989    3.0774    1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  7 21  1  0
  8 22  1  6
  9 23  1  0
 10 24  1  1
 11 25  1  0
 12 26  1  1
 13 27  1  0
 14 28  1  6
 15 29  1  0
M  END


  Mrv1652309032202032D          

 15 15  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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  2  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
    0.0000    0.0000    0.0000 C   0  0  1  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 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0165047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C[C@H](O)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O6/c1-4(10)15-3-5-2-6(11)8(13)9(14)7(5)12/h2,6-9,11-14H,3H2,1H3/t6-,7-,8-,9-/m0/s1

> <INCHI_KEY>
QBVXDOMUJIZMRX-JBDRJPRFSA-N

> <FORMULA>
C9H14O6

> <MOLECULAR_WEIGHT>
218.205

> <EXACT_MASS>
218.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.7062947072394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4S,5S,6S)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-2.5904085693333325

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.571877093512313

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.654308432829957

> <JCHEM_PKA_STRONGEST_BASIC>
-3.360856897610434

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
49.376799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4S,5S,6S)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₄O₆

Average Mass

218.2050 Da

Monoisotopic Mass

218.07904 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C[C@H](O)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C9H14O6/c1-4(10)15-3-5-2-6(11)8(13)9(14)7(5)12/h2,6-9,11-14H,3H2,1H3/t6-,7-,8-,9-/m0/s1

InChI Key

QBVXDOMUJIZMRX-JBDRJPRFSA-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 cyclitols and derivatives. Cyclitols and derivatives are compounds containing a cycloalkane moiety with one hydroxyl group on each of three or more ring atoms. These of also include derivatives where the hydrogen atom of one or more of the hydroxyl groups is replaced with another atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclitols and derivatives

Alternative Parents

Substituents

Cyclitol or derivatives
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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

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

8618777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10443358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mondal S, Prathap A, Sureshan KM: Vinylogy in orthoester hydrolysis: total syntheses of cyclophellitol, valienamine, gabosine K, valienone, gabosine G, 1-epi-streptol, streptol, and uvamalol A. J Org Chem. 2013 Aug 2;78(15):7690-700. doi: 10.1021/jo401272j. Epub 2013 Jul 24. [PubMed:23879653 ]
Yuan P, Liu X, Yang X, Zhang Y, Chen X: Total Syntheses of (+)-Gabosine P, (+)-Gabosine Q, (+)-Gabosine E, (-)-Gabosine G, (-)-Gabosine I, (-)-Gabosine K, (+)-Streptol, and (-)-Uvamalol A by a Diversity-Oriented Approach Featuring Tunable Deprotection Manipulation. J Org Chem. 2017 Apr 7;82(7):3692-3701. doi: 10.1021/acs.joc.7b00181. Epub 2017 Mar 20. [PubMed:28276688 ]
LOTUS database [Link]

Showing NP-Card for [(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate (NP0165047)

MOL for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

3D MOL for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

3D SDF for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

3D-SDF for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

PDB for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

3D PDB for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

SMILES for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

INCHI for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

Structure for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)

3D Structure for NP0165047 ([(3s,4s,5s,6s)-3,4,5,6-tetrahydroxycyclohex-1-en-1-yl]methyl acetate)