NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0218030)

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Record Information

Version

1.0

Created at

2022-09-05 18:33:37 UTC

Updated at

2022-09-05 18:33:37 UTC

NP-MRD ID

NP0218030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(3R,6S)-3,7-Dimethyl-6-(beta-D-glucopyranosyloxy)-1-octene-3,7-diol belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Diplospora dubia. Based on a literature review very few articles have been published on (3R,6S)-3,7-Dimethyl-6-(beta-D-glucopyranosyloxy)-1-octene-3,7-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220332D          

 24 24  0  0  1  0            999 V2000
   -2.1434    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   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
    0.0000    2.4750    0.0000 C   0  0  2  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
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    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 O   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
   -0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  6  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218030

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O8/c1-5-16(4,22)7-6-10(15(2,3)21)24-14-13(20)12(19)11(18)9(8-17)23-14/h5,9-14,17-22H,1,6-8H2,2-4H3/t9-,10+,11-,12+,13-,14+,16+/m1/s1

> <INCHI_KEY>
KOPYZLMAIKVLRO-YECZKKJWSA-N

> <FORMULA>
C16H30O8

> <MOLECULAR_WEIGHT>
350.408

> <EXACT_MASS>
350.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.16242438939217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(3S,6R)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-1.2637820036666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.160509288253731

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205695187072116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.928375087407284

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
84.96750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(3S,6R)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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      -4.001   1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.231   2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.771   5.184   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335   3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.540   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.540   6.160   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
(3R,6S)-3,7-Dimethyl-6-(b-D-glucopyranosyloxy)-1-octene-3,7-diol	Generator
(3R,6S)-3,7-Dimethyl-6-(β-D-glucopyranosyloxy)-1-octene-3,7-diol	Generator

Chemical Formula

C₁₆H₃₀O₈

Average Mass

350.4080 Da

Monoisotopic Mass

350.19407 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(3S,6R)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{[(3S,6R)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H30O8/c1-5-16(4,22)7-6-10(15(2,3)21)24-14-13(20)12(19)11(18)9(8-17)23-14/h5,9-14,17-22H,1,6-8H2,2-4H3/t9-,10+,11-,12+,13-,14+,16+/m1/s1

InChI Key

KOPYZLMAIKVLRO-YECZKKJWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diplospora dubia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
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	-1.3	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	84.97 m³·mol⁻¹	ChemAxon
Polarizability	36.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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

62569234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38351994

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,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0218030)

MOL for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0218030 ((2s,3r,4s,5s,6r)-2-{[(3s,6r)-2,6-dihydroxy-2,6-dimethyloct-7-en-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)