NP-MRD: Showing NP-Card for (2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate (NP0156218)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 13:23:57 UTC

Updated at

2022-09-02 13:23:57 UTC

NP-MRD ID

NP0156218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate

Description

(2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. (2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate is found in Grifola frondosa. Based on a literature review very few articles have been published on (2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    3.2364    1.5388    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    1.4186   -0.2703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    0.3212   -0.1871 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6596   -0.4369   -1.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -0.8004   -1.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6760   -1.6130   -0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -1.8951   -0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -2.0897    0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0476    0.9136   -0.0197 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0876    1.6706    1.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1372    3.0354    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -0.1157   -0.0941 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0013   -0.7371   -1.3722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    0.2851    0.1396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6988    0.8908    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.1265    2.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -0.9639    0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0844   -1.1709   -0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8222   -2.4512   -1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3165   -0.2409   -1.7418 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    2.4528    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697    0.6793    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456    1.7955    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397   -0.2420    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4014    0.2155   -2.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -1.3744   -1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3561   -2.8359   -0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888   -1.0233   -0.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588   -2.0185   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    1.6176   -0.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    3.3977    0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0302    3.3704    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    3.5472    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227   -0.9865    0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -1.4743   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825    0.9396   -0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2915    1.8888    1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8295    1.0518    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837   -0.3474    2.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450   -2.5173   -2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6319   -2.5052   -0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1368   -3.3173   -0.9512 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  6
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
M  END


  Mrv1652309022215232D          

 20 19  0  0  1  0            999 V2000
    7.8079    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2368    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0156218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H](COC(C)=O)[C@H](OC)[C@H](O)[C@H](CO)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O8/c1-7(14)19-6-10(17-3)12(18-4)11(16)9(5-13)20-8(2)15/h9-13,16H,5-6H2,1-4H3/t9-,10+,11+,12-/m0/s1

> <INCHI_KEY>
LYWQZAIMCDNLTC-QCNOEVLYSA-N

> <FORMULA>
C12H22O8

> <MOLECULAR_WEIGHT>
294.3

> <EXACT_MASS>
294.131467668

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.80238374320732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-1.5615150206666657

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.677584822678728

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.022728828853282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9890133708126347

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
66.209

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      14.575   8.415   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.241   7.645   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.574   6.105   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.575   3.795   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.908   3.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.908   7.645   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.242   3.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.576   3.025   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      18.576   6.105   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4R,5S)-5-(Acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetic acid	Generator

Chemical Formula

C₁₂H₂₂O₈

Average Mass

294.3000 Da

Monoisotopic Mass

294.13147 Da

IUPAC Name

(2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate

Traditional Name

(2R,3R,4R,5S)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H](COC(C)=O)[C@H](OC)[C@H](O)[C@H](CO)OC(C)=O

InChI Identifier

InChI=1S/C12H22O8/c1-7(14)19-6-10(17-3)12(18-4)11(16)9(5-13)20-8(2)15/h9-13,16H,5-6H2,1-4H3/t9-,10+,11+,12-/m0/s1

InChI Key

LYWQZAIMCDNLTC-QCNOEVLYSA-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
Grifola frondosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Dicarboxylic acid or derivatives
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.36	ALOGPS
logP	-1.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	66.21 m³·mol⁻¹	ChemAxon
Polarizability	28.8 Å³	ChemAxon
Number of Rings	0	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

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

162926710

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,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate (NP0156218)

MOL for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

3D MOL for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

3D SDF for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

3D-SDF for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

PDB for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

3D PDB for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

SMILES for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

INCHI for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

Structure for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)

3D Structure for NP0156218 ((2r,3r,4r,5s)-5-(acetyloxy)-4,6-dihydroxy-2,3-dimethoxyhexyl acetate)