NP-MRD: Showing NP-Card for 2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0302323)

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Record Information

Version

2.0

Created at

2022-09-10 15:48:00 UTC

Updated at

2022-09-10 15:48:01 UTC

NP-MRD ID

NP0302323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-({3,5-Dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol 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. 2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Rhodiola rosea. 2-({3,5-Dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503032D          

 34 35  0  0  0  0            999 V2000
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 31 32  1  0  0  0  0
  7 33  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004201503032D          

 34 35  0  0  0  0            999 V2000
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 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 33  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC(O)C(C)=CCOC1OC(CO)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H38O12/c1-10(2)4-5-12(25)11(3)6-7-31-21-19(30)20(16(27)14(9-24)32-21)34-22-18(29)17(28)15(26)13(8-23)33-22/h4,6,12-30H,5,7-9H2,1-3H3

> <INCHI_KEY>
KQIHNQPLDMKXDC-UHFFFAOYSA-N

> <FORMULA>
C22H38O12

> <MOLECULAR_WEIGHT>
494.534

> <EXACT_MASS>
494.236326664

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.58809764221019

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.32

> <JCHEM_LOGP>
-2.2700990623333346

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.456092889333995

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.938965361092535

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835653396

> <JCHEM_POLAR_SURFACE_AREA>
198.76

> <JCHEM_REFRACTIVITY>
117.52420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.00e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   11   32                                                  
CONECT   32   31                                                            
CONECT   33    7                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₈O₁₂

Average Mass

494.5340 Da

Monoisotopic Mass

494.23633 Da

IUPAC Name

2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC(O)C(C)=CCOC1OC(CO)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C22H38O12/c1-10(2)4-5-12(25)11(3)6-7-31-21-19(30)20(16(27)14(9-24)32-21)34-22-18(29)17(28)15(26)13(8-23)33-22/h4,6,12-30H,5,7-9H2,1-3H3

InChI Key

KQIHNQPLDMKXDC-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
Rhodiola rosea	LOTUS Database	35616633

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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Oxane
Fatty acyl
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	-1.3	ALOGPS
logP	-2.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.52 m³·mol⁻¹	ChemAxon
Polarizability	51.59 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

73236275

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0302323)

MOL for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0302323 (2-({3,5-dihydroxy-2-[(4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl)oxy]-6-(hydroxymethyl)oxan-4-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol)