NP-MRD: Showing NP-Card for 2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid (NP0322303)

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Record Information

Version

2.0

Created at

2022-09-12 01:00:07 UTC

Updated at

2022-09-12 01:00:07 UTC

NP-MRD ID

NP0322303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid

Description

2,6-Dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. 2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid is found in Cistanche tubulosa. 2,6-Dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241506042D          

 24 24  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  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  0  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  0  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
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    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
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(O)=O)=CCOC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O8/c1-9(4-3-5-10(2)15(21)22)6-7-23-16-14(20)13(19)12(18)11(8-17)24-16/h5-6,11-14,16-20H,3-4,7-8H2,1-2H3,(H,21,22)

> <INCHI_KEY>
ASZSYMZCLJJNIT-UHFFFAOYSA-N

> <FORMULA>
C16H26O8

> <MOLECULAR_WEIGHT>
346.376

> <EXACT_MASS>
346.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.22073581801311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid

> <ALOGPS_LOGP>
-0.32

> <JCHEM_LOGP>
-0.07675975066666632

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210523761628352

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.736527171574387

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835511357308

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
85.31259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   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       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
2,6-Dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoate	Generator

Chemical Formula

C₁₆H₂₆O₈

Average Mass

346.3760 Da

Monoisotopic Mass

346.16277 Da

IUPAC Name

2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid

Traditional Name

2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(O)=O)=CCOC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H26O8/c1-9(4-3-5-10(2)15(21)22)6-7-23-16-14(20)13(19)12(18)11(8-17)24-16/h5-6,11-14,16-20H,3-4,7-8H2,1-2H3,(H,21,22)

InChI Key

ASZSYMZCLJJNIT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cistanche tubulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Terpene glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Sugar acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acid
Oxane
Monosaccharide
Fatty acyl
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Primary 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	-0.32	ALOGPS
logP	-0.077	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.31 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid (NP0322303)

MOL for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

3D MOL for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

3D SDF for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

3D-SDF for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

PDB for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

3D PDB for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

SMILES for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

INCHI for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

Structure for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)

3D Structure for NP0322303 (2,6-dimethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octa-2,6-dienoic acid)