NP-MRD: Showing NP-Card for (2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol (NP0267559)

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Record Information

Version

2.0

Created at

2022-09-08 12:22:41 UTC

Updated at

2022-09-08 12:22:41 UTC

NP-MRD ID

NP0267559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol

Description

Nephthoside belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on nephthoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214222D          

 38 39  0  0  1  0            999 V2000
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 37 38  1  0  0  0  0
M  END

     RDKit          3D

 86 87  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309082214222D          

 38 39  0  0  1  0            999 V2000
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   -0.7145   -2.8875    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
   -1.4289   -1.6500    0.0000 C   0  0  1  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   -1.2375    0.0000 C   0  0  1  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   -1.6500    0.0000 C   0  0  2  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   -2.8875    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  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
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  6  0  0  0
 23 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 21 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O)=C(C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-21(2)10-7-11-22(3)12-8-13-23(4)14-9-15-24(5)16-17-26-19-29(25(6)18-27(26)33)38-32-31(36)30(35)28(34)20-37-32/h10,12,14,16,18-19,28,30-36H,7-9,11,13,15,17,20H2,1-6H3/b22-12+,23-14+,24-16+/t28-,30-,31+,32+/m1/s1

> <INCHI_KEY>
ONIXMLBJNWJBFW-POXPZTCHSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
63.02939589388876

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R)-2-{4-hydroxy-2-methyl-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol

> <JCHEM_LOGP>
6.949513235000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.236342557777562

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.753056718286228

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526598505763652

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
156.89350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R)-2-{4-hydroxy-2-methyl-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      14.670  16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32                                                            
CONECT   34   23   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   21   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O)=C(C)C=C1O

InChI Identifier

InChI=1S/C32H48O6/c1-21(2)10-7-11-22(3)12-8-13-23(4)14-9-15-24(5)16-17-26-19-29(25(6)18-27(26)33)38-32-31(36)30(35)28(34)20-37-32/h10,12,14,16,18-19,28,30-36H,7-9,11,13,15,17,20H2,1-6H3/b22-12+,23-14+,24-16+/t28-,30-,31+,32+/m1/s1

InChI Key

ONIXMLBJNWJBFW-POXPZTCHSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Pentose monosaccharide
4-alkoxyphenol
Phenoxy compound
M-cresol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	6.95	ChemAxon
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	13	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

8705603

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10530208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol (NP0267559)

MOL for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

3D MOL for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

3D SDF for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

3D-SDF for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

PDB for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

3D PDB for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

SMILES for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

INCHI for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

Structure for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)

3D Structure for NP0267559 ((2s,3s,4r,5r)-2-{4-hydroxy-2-methyl-5-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenoxy}oxane-3,4,5-triol)