NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0318487)

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Record Information

Version

2.0

Created at

2022-09-11 19:01:08 UTC

Updated at

2022-09-11 19:01:08 UTC

NP-MRD ID

NP0318487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Description

(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221012D          

 36 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112221012D          

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 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC[C@@H](CC2)C(C)(C)O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O12/c1-12(25)31-11-18-19(32-13(2)26)20(33-14(3)27)21(34-15(4)28)23(35-18)36-22(29)16-7-9-17(10-8-16)24(5,6)30/h7,17-21,23,30H,8-11H2,1-6H3/t17-,18+,19+,20-,21+,23-/m0/s1

> <INCHI_KEY>
RVQWXKAZGHLAJI-CTAFWJRSSA-N

> <FORMULA>
C24H34O12

> <MOLECULAR_WEIGHT>
514.524

> <EXACT_MASS>
514.205026535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.977359957288016

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <JCHEM_LOGP>
1.0957569879999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.4022518552903

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8731234101683792

> <JCHEM_POLAR_SURFACE_AREA>
160.96

> <JCHEM_REFRACTIVITY>
119.2163

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.233 -11.344   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.773  -8.676   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667  -4.620   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   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   15   21                                                       
CONECT   21   20   12                                                       
CONECT   22    8   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27    6   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-3,4,5-Tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid	Generator

Chemical Formula

C₂₄H₃₄O₁₂

Average Mass

514.5240 Da

Monoisotopic Mass

514.20503 Da

IUPAC Name

(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Traditional Name

(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC[C@@H](CC2)C(C)(C)O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C24H34O12/c1-12(25)31-11-18-19(32-13(2)26)20(33-14(3)27)21(34-15(4)28)23(35-18)36-22(29)16-7-9-17(10-8-16)24(5,6)30/h7,17-21,23,30H,8-11H2,1-6H3/t17-,18+,19+,20-,21+,23-/m0/s1

InChI Key

RVQWXKAZGHLAJI-CTAFWJRSSA-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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Pentacarboxylic acid or derivatives
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.1	ChemAxon
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	160.96 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	119.22 m³·mol⁻¹	ChemAxon
Polarizability	51.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

162910957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0318487)

MOL for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D MOL for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D SDF for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D-SDF for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

PDB for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D PDB for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

SMILES for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

INCHI for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

Structure for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D Structure for NP0318487 ((2s,3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)