NP-MRD: Showing NP-Card for 2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0290856)

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Record Information

Version

2.0

Created at

2022-09-09 21:43:47 UTC

Updated at

2022-09-09 21:43:47 UTC

NP-MRD ID

NP0290856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(X)-2-Heptanol glucoside 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 (x)-2-Heptanol glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (x)-2-Heptanol glucoside has been detected, but not quantified in, herbs and spices. 2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Lessingia glandulifera. This could make (X)-2-heptanol glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
    3.1417    2.2793   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0315    1.1812    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169    0.0915   -0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.5676   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2613   -1.1768    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577   -1.8703   -0.1106 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2074   -2.9749   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474   -0.9377   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629   -0.8150    0.3109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0720    0.4005    0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9624    1.3214    0.4369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7987    2.6190    1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832    3.5943    0.7655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013    0.8696    0.5804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1328    1.4546   -0.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140   -0.6287    0.4476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7405   -1.0087   -0.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389   -1.1959   -0.3225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4644   -2.5846   -0.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0838    1.9473   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4552    2.5020   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051    3.1569    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    1.6503    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6805    0.7606    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    0.4159   -1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237   -0.7185   -0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.2322   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -1.2873   -1.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571   -0.3490    0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -1.8692    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5882   -2.3393    0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6559   -2.6078   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.5239   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804   -3.7154   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8838   -1.5719    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7351    1.5308   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7758    3.0358    1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.4824    2.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939    3.3114    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7853    1.2304    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0304    1.7513   -0.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581   -1.0545    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6467   -1.3501   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575   -0.7931   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3914   -2.8784   -0.1980 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  1
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  1
 11 36  1  6
 12 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 16 42  1  1
 17 43  1  0
 18 44  1  6
 19 45  1  0
M  END


  Mrv0541 05061308122D          

 19 19  0  0  0  0            999 V2000
    0.7145    4.5375    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
    1.4289    4.9500    0.0000 C   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
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
 19  9  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H26O6/c1-3-4-5-6-8(2)18-13-12(17)11(16)10(15)9(7-14)19-13/h8-17H,3-7H2,1-2H3

> <INCHI_KEY>
NZLSMMMVSHTELV-UHFFFAOYSA-N

> <FORMULA>
C13H26O6

> <MOLECULAR_WEIGHT>
278.3419

> <EXACT_MASS>
278.172938564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.434073169058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.3401986550000001

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200101152348306

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21058993791913

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835402761526

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
68.16900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      14.671  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.003  13.090   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    9   14                                                       
CONECT    8    2    6   18                                                  
CONECT    9    7   10   19                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   18   19                                                  
CONECT   14    7                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18    8   13                                                       
CONECT   19    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₆O₆

Average Mass

278.3419 Da

Monoisotopic Mass

278.17294 Da

IUPAC Name

2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CCCCCC(C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H26O6/c1-3-4-5-6-8(2)18-13-12(17)11(16)10(15)9(7-14)19-13/h8-17H,3-7H2,1-2H3

InChI Key

NZLSMMMVSHTELV-UHFFFAOYSA-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
Lessingia glandulifera	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
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	0.58	ALOGPS
logP	0.34	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.17 m³·mol⁻¹	ChemAxon
Polarizability	30.43 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

HMDB0035028

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013634

KNApSAcK ID

Not Available

Chemspider ID

11194046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14138808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0290856)

MOL for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0290856 (2-(heptan-2-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol)