NP-MRD: Showing NP-Card for Ophrysanin (NP0054549)

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Record Information

Version

2.0

Created at

2022-04-28 00:52:11 UTC

Updated at

2022-04-28 00:52:11 UTC

NP-MRD ID

NP0054549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophrysanin

Description

Ophrysanin is found in Anacamptis pyramidalis , Barlia spp., Cephalanthera spp., Epipactis atrorubens, Himantoglossum adriaticum, Limodorum abortivum, Neottianthe cucullata, Nigritella spp., Ophrys spp., Orchis spp., Serapias spp. and Traunsteinera globosa.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202522D          

 37 40  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 14 26  1  6  0  0  0
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  8 28  1  0  0  0  0
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 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
  3 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
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   -2.3546    1.1720    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 36  1  0
 36  8  1  0
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  7  6  1  0
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  2  1  2  0
  8  9  1  0
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 17 18  2  0
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 21 22  1  0
 22 23  2  0
 23 24  1  0
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 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
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 32 33  1  0
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 34 35  1  0
 34 36  1  0
 23 12  1  0
 31 24  1  0
 21 14  1  0
 37 58  1  0
 36 57  1  6
  8 41  1  1
  7 39  1  0
  7 40  1  0
  3 38  1  0
 10 42  1  1
 13 43  1  0
 16 44  1  0
 17 45  1  0
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 25 48  1  0
 26 49  1  0
 28 50  1  0
 30 51  1  0
 31 52  1  0
 32 53  1  1
 33 54  1  0
 34 55  1  6
 35 56  1  0
M  CHG  1  22   1
M  END


  Mrv1652304282202522D          

 37 40  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
  3 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0054549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)C(O)=O)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C(O)=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O14/c24-9-4-12(26)10-6-15(20(35-14(10)5-9)8-1-2-11(25)13(27)3-8)36-23-19(30)18(29)17(28)16(37-23)7-34-22(33)21(31)32/h1-6,16-19,23,28-30H,7H2,(H4-,24,25,26,27,31,32)/p+1/t16-,17-,18-,19+,23-/m1/s1

> <INCHI_KEY>
ADNURPZCKUPWPT-YHSXXIMFSA-O

> <FORMULA>
C23H21O14

> <MOLECULAR_WEIGHT>
521.406

> <EXACT_MASS>
521.092581776

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.79517143059732

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3S,4R,5S,6R)-6-{[(carboxycarbonyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.442999999999999

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.388339876487792

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8002589226044532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64911231307918

> <JCHEM_POLAR_SURFACE_AREA>
236.80999999999995

> <JCHEM_REFRACTIVITY>
127.20389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3S,4R,5S,6R)-6-{[(carboxycarbonyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   15                                                            
CONECT   26   14                                                            
CONECT   27   13                                                            
CONECT   28    8   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32                                                            
CONECT   35   31                                                            
CONECT   36    3                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₁O₁₄

Average Mass

521.4060 Da

Monoisotopic Mass

521.09258 Da

IUPAC Name

3-{[(2S,3S,4R,5S,6R)-6-{[(carboxycarbonyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3S,4R,5S,6R)-6-{[(carboxycarbonyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)C(O)=O)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C(O)=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H20O14/c24-9-4-12(26)10-6-15(20(35-14(10)5-9)8-1-2-11(25)13(27)3-8)36-23-19(30)18(29)17(28)16(37-23)7-34-22(33)21(31)32/h1-6,16-19,23,28-30H,7H2,(H4-,24,25,26,27,31,32)/p+1/t16-,17-,18-,19+,23-/m1/s1

InChI Key

ADNURPZCKUPWPT-YHSXXIMFSA-O

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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anacamptis pyramidalis	Plant	KNApSAcK
Barlia spp.	Plant	KNApSAcK
Cephalanthera spp.	Plant	KNApSAcK
Epipactis atrorubens	Plant	KNApSAcK
Himantoglossum adriaticum	Plant	KNApSAcK
Limodorum abortivum	Plant	KNApSAcK
Neottianthe cucullata	Plant	KNApSAcK
Nigritella spp.	Plant	KNApSAcK
Ophrys spp.	Plant	KNApSAcK
Orchis spp.	Plant	KNApSAcK
Serapias spp.	Plant	KNApSAcK
Traunsteinera globosa	Plant	KNApSAcK

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	1.74	ALOGPS
logP	1.44	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	236.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.2 m³·mol⁻¹	ChemAxon
Polarizability	47.8 Å³	ChemAxon
Number of Rings	4	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

Not Available

Showing NP-Card for Ophrysanin (NP0054549)

MOL for NP0054549 (Ophrysanin)

3D MOL for NP0054549 (Ophrysanin)

3D SDF for NP0054549 (Ophrysanin)

3D-SDF for NP0054549 (Ophrysanin)

PDB for NP0054549 (Ophrysanin)

3D PDB for NP0054549 (Ophrysanin)

SMILES for NP0054549 (Ophrysanin)

INCHI for NP0054549 (Ophrysanin)

Structure for NP0054549 (Ophrysanin)

3D Structure for NP0054549 (Ophrysanin)