NP-MRD: Showing NP-Card for (3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate (NP0220068)

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Record Information

Version

2.0

Created at

2022-09-05 21:16:27 UTC

Updated at

2022-09-05 21:16:27 UTC

NP-MRD ID

NP0220068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate

Description

(3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate is found in Ajuga reptans.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223162D          

 26 27  0  0  0  0            999 V2000
    3.3400   -1.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -2.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -2.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -1.8619    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
    0.8769   -1.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -4.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -4.9932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0231   -2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0339   -3.5541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -3.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316   -3.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -4.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -2.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -1.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485   -1.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -1.6431    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1652309052223162D          

 26 27  0  0  0  0            999 V2000
    3.3400   -1.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879   -2.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429   -2.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810   -1.8619    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
    0.8769   -1.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890   -4.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -4.9932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0231   -2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0339   -3.5541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -3.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316   -3.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -4.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7747   -2.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3770   -1.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5485   -1.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -1.6431    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)CC\C(=C\CO)C1COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O9/c1-9(20)26-17(2)5-3-10(4-6-18)11(17)8-24-16-15(23)14(22)13(21)12(7-19)25-16/h4,11-16,18-19,21-23H,3,5-8H2,1-2H3/b10-4-

> <INCHI_KEY>
GVJSQKBHGQEZPM-WMZJFQQLSA-N

> <FORMULA>
C17H28O9

> <MOLECULAR_WEIGHT>
376.402

> <EXACT_MASS>
376.173332482

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.06484787903026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate

> <JCHEM_LOGP>
-2.197920709000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19992691697895

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21092039896191

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2351356966917013

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
88.95330000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.235  -2.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.204  -3.796   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.680  -5.260   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.698  -3.476   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.637  -3.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.992  -8.236   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.539  -8.075   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.445  -9.321   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.043  -5.049   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.188  -6.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.652  -5.604   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.797  -6.634   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.261  -6.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.406  -7.189   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.086  -8.695   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.581  -4.652   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.046  -4.176   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.437  -3.622   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.757  -2.115   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.972  -4.098   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.828  -3.067   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    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₈O₉

Average Mass

376.4020 Da

Monoisotopic Mass

376.17333 Da

IUPAC Name

(3Z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate

Traditional Name

(3Z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)CC\C(=C\CO)C1COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C17H28O9/c1-9(20)26-17(2)5-3-10(4-6-18)11(17)8-24-16-15(23)14(22)13(21)12(7-19)25-16/h4,11-16,18-19,21-23H,3,5-8H2,1-2H3/b10-4-

InChI Key

GVJSQKBHGQEZPM-WMZJFQQLSA-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
Ajuga reptans	LOTUS Database	35616633

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	-2.2	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	88.95 m³·mol⁻¹	ChemAxon
Polarizability	38.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate (NP0220068)

MOL for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

3D MOL for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

3D SDF for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

3D-SDF for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

PDB for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

3D PDB for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

SMILES for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

INCHI for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

Structure for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)

3D Structure for NP0220068 ((3z)-3-(2-hydroxyethylidene)-1-methyl-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)cyclopentyl acetate)