NP-MRD: Showing NP-Card for (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+ (NP0024227)

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Record Information

Version

2.0

Created at

2021-06-19 16:39:52 UTC

Updated at

2021-06-29 23:48:25 UTC

NP-MRD ID

NP0024227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+

Provided By

JEOL Database JEOL Logo

Description

(1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+ is found in Anethum graveolens L. (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+ was first documented in 2002 (Ishikawa, T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118393D          

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     RDKit          3D

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M  END


  Mrv1652306192118393D          

 68 70  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0024227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@@]2([H])C([H])([H])[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2(O[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[C@]1([H])OC([H])([H])[C@@](O[H])(C([H])([H])O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O11/c1-10(2)11-4-5-20(3,27)13(6-11)31-18-15(25)14(24)16(12(7-22)30-18)32-19-17(26)21(28,8-23)9-29-19/h11-19,22-28H,1,4-9H2,2-3H3/t11-,12-,13+,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
GFGMBFZXYDTVRW-FENRXTRFSA-N

> <FORMULA>
C21H36O11

> <MOLECULAR_WEIGHT>
464.508

> <EXACT_MASS>
464.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.49556569689776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-{[(1S,2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4-diol

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-1.890007134666667

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.361725639911253

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.720778179114575

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9813780709212736

> <JCHEM_POLAR_SURFACE_AREA>
178.53

> <JCHEM_REFRACTIVITY>
107.8344

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-{[(1S,2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.871  -3.293   0.565  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.827  -3.215   1.409  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.041  -2.723   2.820  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.382  -3.561   1.047  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.028  -4.904   1.678  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.482  -5.275   1.372  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.819  -5.231  -0.128  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.319  -5.481  -0.324  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.153  -6.307  -0.804  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.398  -3.878  -0.761  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.206  -2.822  -0.219  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.670  -1.899  -1.213  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.576  -1.216  -1.819  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.018  -0.299  -2.831  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.766   0.282  -3.502  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.027   1.087  -2.577  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.887   0.813  -2.214  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.360   1.651  -3.276  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.415   3.030  -2.917  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.442   3.691  -3.678  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.879   4.879  -4.258  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.566   5.157  -3.539  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.638   5.846  -4.385  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.763   5.991  -2.262  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.495   6.228  -1.639  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.093   3.732  -3.273  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.095   3.657  -2.250  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.069   0.183  -1.461  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.771   1.185  -0.707  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.586  -0.897  -0.492  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.729  -1.553   0.082  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.080  -3.574  -0.467  0.00  0.00           C+0
HETATM   33  H   UNK     0       3.874  -3.020   0.883  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.778  -3.631  -0.461  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.078  -2.417   2.998  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.801  -3.505   3.545  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.405  -1.854   3.019  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.246  -2.773   1.487  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.091  -4.867   2.768  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.639  -5.702   1.326  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.138  -4.588   1.922  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.667  -6.282   1.767  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.579  -5.460  -1.388  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.598  -6.475   0.043  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.934  -4.740   0.197  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.220  -6.327  -0.536  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.525  -3.947  -1.850  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.240  -2.463  -1.963  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.578  -0.851  -3.596  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.028   0.907  -4.361  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.102  -0.518  -3.847  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.279   0.467  -1.883  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.294   1.391  -1.493  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.666   3.151  -1.858  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.722   4.694  -5.327  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.598   5.700  -4.170  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.938   6.178  -3.785  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.177   6.974  -2.509  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.426   5.512  -1.535  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.094   5.341  -1.498  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.654   3.309  -4.185  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.626   2.799  -2.384  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.798  -0.226  -2.172  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.453   0.698  -0.203  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.050  -0.428   0.343  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.364  -2.270   0.637  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.347  -2.596  -0.886  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.700  -4.321  -0.977  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    4    1    3                                                  
CONECT    3    2   35   36   37                                             
CONECT    4    5   32    2   38                                             
CONECT    5    6    4   39   40                                             
CONECT    6    7    5   41   42                                             
CONECT    7    6   10    9    8                                             
CONECT    8    7   43   44   45                                             
CONECT    9    7   46                                                       
CONECT   10   32    7   11   47                                             
CONECT   11   10   12                                                       
CONECT   12   13   30   11   48                                             
CONECT   13   14   12                                                       
CONECT   14   17   13   15   49                                             
CONECT   15   16   14   50   51                                             
CONECT   16   15   52                                                       
CONECT   17   28   14   18   53                                             
CONECT   18   17   19                                                       
CONECT   19   26   20   18   54                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   55   56                                             
CONECT   22   26   23   24   21                                             
CONECT   23   22   57                                                       
CONECT   24   25   22   58   59                                             
CONECT   25   24   60                                                       
CONECT   26   22   19   27   61                                             
CONECT   27   26   62                                                       
CONECT   28   30   17   29   63                                             
CONECT   29   28   64                                                       
CONECT   30   28   31   12   65                                             
CONECT   31   30   66                                                       
CONECT   32    4   10   67   68                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   19                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   32                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

RDKit          3D

68 70  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₆O₁₁

Average Mass

464.5080 Da

Monoisotopic Mass

464.22576 Da

IUPAC Name

(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-{[(1S,2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4-diol

Traditional Name

(2S,3R,4R,5S,6R)-5-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-{[(1S,2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4-diol

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@@]2([H])C([H])([H])[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2(O[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[C@]1([H])OC([H])([H])[C@@](O[H])(C([H])([H])O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C21H36O11/c1-10(2)11-4-5-20(3,27)13(6-11)31-18-15(25)14(24)16(12(7-22)30-18)32-19-17(26)21(28,8-23)9-29-19/h11-19,22-28H,1,4-9H2,2-3H3/t11-,12-,13+,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

GFGMBFZXYDTVRW-FENRXTRFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anethum graveolens	JEOL database	Ishikawa, T., et al, Chem. Pharm. Bull. 50, 501 (2002)

Chemical Taxonomy

Classification

Not classified

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	-1.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.72	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.83 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Ishikawa, T., et al. (2002). Ishikawa, T., et al, Chem. Pharm. Bull. 50, 501 (2002). Chem. Pharm. Bull..

Showing NP-Card for (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+ (NP0024227)

MOL for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

3D MOL for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

3D SDF for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

3D-SDF for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

PDB for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

3D PDB for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

SMILES for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

INCHI for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

Structure for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)

3D Structure for NP0024227 ( (1S,2S,4R)-p-menth-8-ene-1,2-diol 2-O-beta-D-apiofuranosyl-(1-6)-beta-D-+)