NP-MRD: Showing NP-Card for baccharisol (NP0184390)

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Record Information

Version

2.0

Created at

2022-09-03 23:30:36 UTC

Updated at

2022-09-03 23:30:37 UTC

NP-MRD ID

NP0184390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

baccharisol

Description

baccharisol is found in Baccharis megapotamica. Based on a literature review very few articles have been published on (1'R,2S,3'R,6'R,8'R,12'S,13'R,17'R,18'Z,20'Z,24'R,25'S)-6',12'-dihydroxy-17'-[(1S)-1-hydroxyethyl]-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0³,⁸.0⁸,²⁵]Heptacosane]-4',18',20'-triene-11',22'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042201302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042201302D          

 39 43  0  0  1  0            999 V2000
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    5.0638    1.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7623    1.4817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7570    2.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506   -0.3687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6606    0.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6855   -0.9605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2746   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4802   -1.1820    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  1  0  0  0
 31 35  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0184390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@@H]1OCC[C@@H](C)[C@H](O)C(=O)OC[C@]23C[C@@H](O)C(C)=C[C@H]2O[C@@H]2C[C@@H](OC(=O)\C=C/C=C\1)[C@@]3(C)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O10/c1-16-9-10-35-20(18(3)30)7-5-6-8-24(32)39-21-12-23-29(15-37-29)27(21,4)28(14-36-26(34)25(16)33)13-19(31)17(2)11-22(28)38-23/h5-8,11,16,18-23,25,30-31,33H,9-10,12-15H2,1-4H3/b7-5-,8-6-/t16-,18+,19-,20-,21-,22-,23-,25+,27-,28-,29+/m1/s1

> <INCHI_KEY>
GVZIONLFUHXCGG-ZNZUEGHHSA-N

> <FORMULA>
C29H40O10

> <MOLECULAR_WEIGHT>
548.629

> <EXACT_MASS>
548.262147488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.58644348550903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2S,3'R,6'R,8'R,12'S,13'R,17'R,18'E,20'Z,24'R,25'S)-6',12'-dihydroxy-17'-[(1S)-1-hydroxyethyl]-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',18',20'-triene-11',22'-dione

> <JCHEM_LOGP>
1.0540341919999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.218528704664287

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.469770662685079

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9800218614887184

> <JCHEM_POLAR_SURFACE_AREA>
144.28000000000003

> <JCHEM_REFRACTIVITY>
140.5252

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,3'R,6'R,8'R,12'S,13'R,17'R,18'E,20'Z,24'R,25'S)-6',12'-dihydroxy-17'-[(1S)-1-hydroxyethyl]-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',18',20'-triene-11',22'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      13.417   2.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.072   1.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.053   0.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.702  -0.388   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.740  -2.026   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.393  -2.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.816  -3.355   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.906  -1.985   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.360  -2.230   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.492  -3.521   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.146  -4.915   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.950  -3.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.766  -2.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.826  -1.142   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.301   0.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.257   1.866   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.268   2.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.217   0.870   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.843   3.511   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.732   3.351   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.684   4.595   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.003   5.447   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.528   5.828   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.412   7.364   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.094   5.679   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.712   7.090   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.267   4.628   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.660   5.284   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.330   3.029   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.008   1.556   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.220   0.380   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.452   1.963   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.756   2.766   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.746   4.306   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.934  -0.688   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.833   0.388   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.746  -1.793   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.846  -0.715   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.230  -2.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    4   32   35                                             
CONECT   32   31   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
CONECT   35   31    8   36   37                                             
CONECT   36   35                                                            
CONECT   37   35    6   38   39                                             
CONECT   38   37   39                                                       
CONECT   39   38   37                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₁₀

Average Mass

548.6290 Da

Monoisotopic Mass

548.26215 Da

IUPAC Name

(1'R,2S,3'R,6'R,8'R,12'S,13'R,17'R,18'E,20'Z,24'R,25'S)-6',12'-dihydroxy-17'-[(1S)-1-hydroxyethyl]-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^{3,8}.0^{8,25}]heptacosane]-4',18',20'-triene-11',22'-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H]1OCC[C@@H](C)[C@H](O)C(=O)OC[C@]23C[C@@H](O)C(C)=C[C@H]2O[C@@H]2C[C@@H](OC(=O)\C=C/C=C\1)[C@@]3(C)[C@]21CO1

InChI Identifier

InChI=1S/C29H40O10/c1-16-9-10-35-20(18(3)30)7-5-6-8-24(32)39-21-12-23-29(15-37-29)27(21,4)28(14-36-26(34)25(16)33)13-19(31)17(2)11-22(28)38-23/h5-8,11,16,18-23,25,30-31,33H,9-10,12-15H2,1-4H3/b7-5-,8-6-/t16-,18+,19-,20-,21-,22-,23-,25+,27-,28-,29+/m1/s1

InChI Key

GVZIONLFUHXCGG-ZNZUEGHHSA-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
Baccharis megapotamica	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	1.05	ChemAxon
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	144.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	140.53 m³·mol⁻¹	ChemAxon
Polarizability	56.59 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

52085235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for baccharisol (NP0184390)

MOL for NP0184390 (baccharisol)

3D MOL for NP0184390 (baccharisol)

3D SDF for NP0184390 (baccharisol)

3D-SDF for NP0184390 (baccharisol)

PDB for NP0184390 (baccharisol)

3D PDB for NP0184390 (baccharisol)

SMILES for NP0184390 (baccharisol)

INCHI for NP0184390 (baccharisol)

Structure for NP0184390 (baccharisol)

3D Structure for NP0184390 (baccharisol)