NP-MRD: Showing NP-Card for compound 5 in CDCl3 (NP0332350)

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Record Information

Version

1.0

Created at

2024-01-09 12:23:52 UTC

Updated at

2024-09-03 04:18:53 UTC

NP-MRD ID

NP0332350

DOI

https://doi.org/10.57994/1552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

compound 5 in CDCl3

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01092412232D          

 34 36  0  0  1  0            999 V2000
    0.0327    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1579   -0.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -2.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -2.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2056   -2.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341   -3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -2.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755   -3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1727   -2.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4168   -4.0627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1325   -4.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609   -5.4706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3766   -6.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4738   -5.3297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4715   -6.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2859   -5.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582   -4.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -3.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5141   -3.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0857    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2187   -1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 24  1  0  0  0  0
 26 27  1  6  0  0  0
 28 26  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30  2  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END


  Mrv2104 01092412232D          

 34 36  0  0  1  0            999 V2000
    0.0327    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1579   -0.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -2.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928   -2.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2056   -2.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341   -3.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -2.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755   -3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1727   -2.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4168   -4.0627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1325   -4.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6609   -5.4706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3766   -6.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4738   -5.3297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4715   -6.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2859   -5.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582   -4.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -3.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5141   -3.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    1.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0857    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2187   -1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 24  1  0  0  0  0
 26 27  1  6  0  0  0
 28 26  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30  2  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC(=O)C(C)([C@@H](O)[C@@H]1C)[C@]2(C)\C=C\C=C\C=C\C=C\C=C(/C)[C@H]1O[C@@H](C)[C@@](C)(O)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O5/c1-18(22-19(2)17-27(6,31)21(4)32-22)15-13-11-9-8-10-12-14-16-26(5)24-20(3)23(29)28(26,7)25(30)33-24/h8-17,20-24,29,31H,1-7H3/b9-8+,12-10+,13-11+,16-14+,18-15+/t20-,21-,22+,23-,24+,26+,27-,28?/m0/s1

> <INCHI_KEY>
ZYKLPRUPLDQMRJ-PKMLVBQLSA-N

> <FORMULA>
C28H38O5

> <MOLECULAR_WEIGHT>
454.607

> <EXACT_MASS>
454.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.01181982956554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S,6S,7S)-5-hydroxy-7-[(1E,3E,5E,7E,9E)-10-[(2R,5S,6S)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]undeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one

> <JCHEM_LOGP>
4.165477708666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.264489515978758

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.539597844840907

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1756246861520725

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
136.40340000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6S,7S)-5-hydroxy-7-[(1E,3E,5E,7E,9E)-10-[(2R,5S,6S)-5-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]undeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JAN-24         0                                  
HETATM    1  C   UNK     0       0.061   0.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.295  -1.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.891  -2.723   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.096  -3.906   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.613  -3.643   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.600  -4.825   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.117  -4.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.104  -5.745   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.621  -5.482   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.608  -6.664   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.125  -6.401   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.656  -4.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.111  -7.584   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -9.581  -9.029   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -10.567 -10.212   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.036 -11.657   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.084  -9.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.080 -11.489   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -13.600 -10.220   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -12.615  -8.503   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -11.629  -7.321   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.160  -5.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.438   3.356   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.160   2.591   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.408  -1.998   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       2.249  -2.839   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0       3.583  -0.529   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.106   1.600   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   14   23                                                  
CONECT   23   22                                                            
CONECT   24    2   25   26   33                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31    2   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   24   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₅

Average Mass

454.6070 Da

Monoisotopic Mass

454.27192 Da

IUPAC Name

(1R,5S,6S,7S)-5-hydroxy-7-[(1E,3E,5E,7E,9E)-10-[(2R,5S,6S)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]undeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one

Traditional Name

(1R,5S,6S,7S)-5-hydroxy-7-[(1E,3E,5E,7E,9E)-10-[(2R,5S,6S)-5-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]undeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptan-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC(=O)C(C)([C@@H](O)[C@@H]1C)[C@]2(C)\C=C\C=C\C=C\C=C\C=C(/C)[C@H]1O[C@@H](C)[C@@](C)(O)C=C1C

InChI Identifier

InChI=1S/C28H38O5/c1-18(22-19(2)17-27(6,31)21(4)32-22)15-13-11-9-8-10-12-14-16-26(5)24-20(3)23(29)28(26,7)25(30)33-24/h8-17,20-24,29,31H,1-7H3/b9-8+,12-10+,13-11+,16-14+,18-15+/t20-,21-,22+,23-,24+,26+,27-,28?/m0/s1

InChI Key

ZYKLPRUPLDQMRJ-PKMLVBQLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C2D6OS, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-01-09	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.133121014, CDCl₃, simulated)	838071903@qq.com	jinan university	FuLong Lin	2024-05-02	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sp. JNU18266-02		Not Available

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	4.17	ChemAxon
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.4 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Lin FL, Gao JL, Xu Q, Wang GQ, Xiao LY, Dong L, Tang W, Lv JM, Chen GD, Wang Y, Yin ZN, Lu LG, Hu D, Gao H: Absolute Configuration of Oxabornyl Polyenes Prugosenes A1-A3 and Structural Revision of Prugosene A2. J Nat Prod. 2024 Mar 6. doi: 10.1021/acs.jnatprod.3c01143. [PubMed:38447084 ]

Showing NP-Card for compound 5 in CDCl3 (NP0332350)

MOL for NP0332350 (compound 5 in CDCl3)

3D MOL for NP0332350 (compound 5 in CDCl3)

3D SDF for NP0332350 (compound 5 in CDCl3)

3D-SDF for NP0332350 (compound 5 in CDCl3)

PDB for NP0332350 (compound 5 in CDCl3)

3D PDB for NP0332350 (compound 5 in CDCl3)

SMILES for NP0332350 (compound 5 in CDCl3)

INCHI for NP0332350 (compound 5 in CDCl3)

Structure for NP0332350 (compound 5 in CDCl3)

3D Structure for NP0332350 (compound 5 in CDCl3)