NP-MRD: Showing NP-Card for (1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone (NP0313588)

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Record Information

Version

2.0

Created at

2022-09-11 11:15:01 UTC

Updated at

2022-09-11 11:15:01 UTC

NP-MRD ID

NP0313588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone

Description

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213152D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112213152D          

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   -2.3320   -1.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254   -0.7841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0479   -1.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -0.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -0.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 18 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 21  1  6  0  0  0
 14 23  1  0  0  0  0
  9 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 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
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0313588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1[C@@H]2O[C@]34O[C@@]5(CC[C@@]6(C)[C@@H]3[C@@](O)([C@@H]2OC1=O)[C@@](C)(O)C6=O)C[C@]12OC(=O)C[C@H]1OC(C)(C)[C@H]2CC=C5C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O11/c1-12-17-19(36-20(12)32)28(35)21-24(4,22(33)25(28,5)34)8-9-26-11-27-14(23(2,3)37-15(27)10-16(30)38-27)7-6-13(26)18(31)29(21,39-17)40-26/h6,12,14-15,17,19,21,34-35H,7-11H2,1-5H3/t12?,14-,15-,17+,19-,21-,24+,25+,26+,27-,28+,29-/m1/s1

> <INCHI_KEY>
IYDZDFROMNTTBD-MMVYJHPISA-N

> <FORMULA>
C29H34O11

> <MOLECULAR_WEIGHT>
558.58

> <EXACT_MASS>
558.210111915

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.43420267684053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,7R,10R,15S,17S,21R,22R,23R,25S,29R)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacos-12-ene-5,14,19,24-tetrone

> <JCHEM_LOGP>
1.7100215046666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.146712339227335

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.80366781087111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.874869771029339

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
131.53950000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,7R,10R,15S,17S,21R,22R,23R,25S,29R)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacos-12-ene-5,14,19,24-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.337  -1.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.218  -0.331   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.391   0.668   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.888   0.306   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.803   2.091   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.268   1.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.906   0.475   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.409   0.073   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.146   1.055   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.679   1.235   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.693   1.065   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.848   2.736   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.147   4.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.756   3.969   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.134   5.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.797   5.171   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.424   6.665   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.245   4.612   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.652   6.098   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.764   4.358   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.144   3.053   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.579   3.610   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.616   2.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.315   1.050   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.661   0.096   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.882   1.724   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.332   2.258   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.781   3.731   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.232   1.011   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.265  -0.212   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.663  -1.715   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.353  -2.513   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.272  -3.749   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.207  -3.541   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.221  -1.464   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.956  -2.354   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.514  -1.884   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.035  -0.434   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.565  -0.456   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.429  -1.731   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23   39                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   24   38                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18    6   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   14    9                                                  
CONECT   24   11   25                                                       
CONECT   25   24   26   30   35                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   25   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   11   39                                                  
CONECT   39   38    9   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₁

Average Mass

558.5800 Da

Monoisotopic Mass

558.21011 Da

IUPAC Name

(1S,3R,7R,10R,15S,17S,21R,22R,23R,25S,29R)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacos-12-ene-5,14,19,24-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1[C@@H]2O[C@]34O[C@@]5(CC[C@@]6(C)[C@@H]3[C@@](O)([C@@H]2OC1=O)[C@@](C)(O)C6=O)C[C@]12OC(=O)C[C@H]1OC(C)(C)[C@H]2CC=C5C4=O

InChI Identifier

InChI=1S/C29H34O11/c1-12-17-19(36-20(12)32)28(35)21-24(4,22(33)25(28,5)34)8-9-26-11-27-14(23(2,3)37-15(27)10-16(30)38-27)7-6-13(26)18(31)29(21,39-17)40-26/h6,12,14-15,17,19,21,34-35H,7-11H2,1-5H3/t12?,14-,15-,17+,19-,21-,24+,25+,26+,27-,28+,29-/m1/s1

InChI Key

IYDZDFROMNTTBD-MMVYJHPISA-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
Schisandra grandiflora	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	1.71	ChemAxon
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.54 m³·mol⁻¹	ChemAxon
Polarizability	54.43 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone (NP0313588)

MOL for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

3D MOL for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

3D SDF for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

3D-SDF for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

PDB for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

3D PDB for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

SMILES for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

INCHI for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

Structure for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)

3D Structure for NP0313588 ((1s,3r,7r,10r,15s,17s,21r,22r,23r,25s,29r)-22,23-dihydroxy-9,9,18,23,25-pentamethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacos-12-ene-5,14,19,24-tetrone)