NP-MRD: Showing NP-Card for 3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B (NP0086339)

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Record Information

Version

2.0

Created at

2022-04-29 06:38:56 UTC

Updated at

2022-04-29 06:38:56 UTC

NP-MRD ID

NP0086339

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B

Description

3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B is found in Physalis alkekengi var. franchetii . Based on a literature review very few articles have been published on (1R,2S,5R,8S,9R,12R,17R,18R,21S,24R,26S,27S)-5-hydroxy-12-methoxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]Nonacosa-13,15-diene-4,10,22,29-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208382D          

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    1.8970    0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    1.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2559    2.3413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896    1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    2.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3034    2.8755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6747    3.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    3.6753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153    3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137    4.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  1  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 28 32  1  6  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 24 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  6  0  0  0
 33 37  1  0  0  0  0
 38 37  1  6  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
 21 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C(=O)[C@]34O[C@@]11[C@](O)(CC[C@@]5([H])[C@@]3([H])C=CC3=C[C@@H](CC(=O)[C@]53C)OC)C(=O)O[C@@]1(C)[C@H]1C[C@]2(C)[C@@]([H])(CO4)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O10/c1-24-11-19-26(3)29-20(24)21(31)28(39-29,36-12-17(24)22(32)37-19)16-6-5-13-9-14(35-4)10-18(30)25(13,2)15(16)7-8-27(29,34)23(33)38-26/h5-6,9,14-17,19-20,34H,7-8,10-12H2,1-4H3/t14-,15-,16+,17-,19+,20-,24+,25-,26-,27-,28+,29-/m0/s1

> <INCHI_KEY>
UKFIOFFQSFYJFW-PDQAFJBESA-N

> <FORMULA>
C29H32O10

> <MOLECULAR_WEIGHT>
540.565

> <EXACT_MASS>
540.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.53559287493289

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,8S,9R,12R,17R,18R,21S,24R,26S,27S)-5-hydroxy-12-methoxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1^{18,27}.0^{1,5}.0^{2,24}.0^{8,17}.0^{9,14}.0^{21,26}]nonacosa-13,15-diene-4,10,22,29-tetrone

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.7933982430000002

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.52886809716249

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.632110843854338

> <JCHEM_PKA_STRONGEST_BASIC>
-3.83963950355078

> <JCHEM_POLAR_SURFACE_AREA>
134.66000000000003

> <JCHEM_REFRACTIVITY>
131.8376

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,8S,9R,12R,17R,18R,21S,24R,26S,27S)-5-hydroxy-12-methoxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1^{18,27}.0^{1,5}.0^{2,24}.0^{8,17}.0^{9,14}.0^{21,26}]nonacosa-13,15-diene-4,10,22,29-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       9.835   5.685   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.445   4.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.974   4.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.584   2.678   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      14.114   2.499   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.034   3.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.665   1.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.135   1.621   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.525   3.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.915   4.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.216   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.686   0.565   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.076   1.979   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       6.321   3.321   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       7.996   3.214   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       8.606   1.800   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       7.794   4.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.583   5.705   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.028   5.603   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.793   6.939   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.979   4.449   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.125   2.458   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.498   1.831   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.305   3.292   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.350   4.424   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.773   0.392   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.166   0.221   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.885   1.266   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.263   1.623   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.293   3.247   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.762   0.475   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       1.214  -0.121   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       2.318   2.592   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.541   1.656   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.526   3.383   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       2.344   4.370   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0       1.287   3.733   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.775   4.679   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.433   5.368   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.259   6.365   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.784   6.860   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.322   7.013   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       5.066   8.362   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8    2   10   15                                             
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   42                                             
CONECT   20   19                                                            
CONECT   21   19   22   35   39                                             
CONECT   22   21   23                                                       
CONECT   23   22   13   24   26                                             
CONECT   24   23   25   35                                                  
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32   33                                             
CONECT   29   28   30   31                                                  
CONECT   30   29   38                                                       
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   28   34   35   37                                             
CONECT   34   33                                                            
CONECT   35   33   24   21   36                                             
CONECT   36   35                                                            
CONECT   37   33   38                                                       
CONECT   38   37   30   39                                                  
CONECT   39   38   21   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   19   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₁₀

Average Mass

540.5650 Da

Monoisotopic Mass

540.19955 Da

IUPAC Name

(1R,2S,5R,8S,9R,12R,17R,18R,21S,24R,26S,27S)-5-hydroxy-12-methoxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1^{18,27}.0^{1,5}.0^{2,24}.0^{8,17}.0^{9,14}.0^{21,26}]nonacosa-13,15-diene-4,10,22,29-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@]12C(=O)[C@]34O[C@@]11[C@](O)(CC[C@@]5([H])[C@@]3([H])C=CC3=C[C@@H](CC(=O)[C@]53C)OC)C(=O)O[C@@]1(C)[C@H]1C[C@]2(C)[C@@]([H])(CO4)C(=O)O1

InChI Identifier

InChI=1S/C29H32O10/c1-24-11-19-26(3)29-20(24)21(31)28(39-29,36-12-17(24)22(32)37-19)16-6-5-13-9-14(35-4)10-18(30)25(13,2)15(16)7-8-27(29,34)23(33)38-26/h5-6,9,14-17,19-20,34H,7-8,10-12H2,1-4H3/t14-,15-,16+,17-,19+,20-,24+,25-,26-,27-,28+,29-/m0/s1

InChI Key

UKFIOFFQSFYJFW-PDQAFJBESA-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, 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
Alkekengi officinarum var. franchetii	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	1.53	ALOGPS
logP	1.79	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.84 m³·mol⁻¹	ChemAxon
Polarizability	53.54 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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

C00056550

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

163183929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B (NP0086339)

MOL for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

3D MOL for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

3D SDF for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

3D-SDF for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

PDB for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

3D PDB for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

SMILES for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

INCHI for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

Structure for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)

3D Structure for NP0086339 (3-Methoxy-2,3-dihydro-4,7-didehydrophysalin B)