NP-MRD: Showing NP-Card for paraphaeoketone C (NP0332422)

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Record Information

Version

2.0

Created at

2024-01-23 12:00:53 UTC

Updated at

2024-09-03 04:19:07 UTC

NP-MRD ID

NP0332422

Natural Product DOI

https://doi.org/10.57994/1641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeoketone C

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232412002D          

 34 38  0  0  1  0            999 V2000
    1.1348   -0.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3402    0.1036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9761    0.6292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    1.1061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355    1.7419    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3465    0.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461   -0.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.5555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7604   -1.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6210    0.1735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4459    0.1602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9163    0.7928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086   -0.5808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2628   -1.1994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5890   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300   -0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    0.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4209    0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348    1.0358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4544    1.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134    0.9406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7913    1.7620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538    1.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    2.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3196    0.4058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9383   -0.1400    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983    0.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407   -0.5368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    0.9621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3272    1.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    2.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  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
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 22 26  2  0  0  0  0
 27 21  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 12 30  1  1  0  0  0
 12 31  1  0  0  0  0
 31 25  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END


  Mrv2104 01232412002D          

 34 38  0  0  1  0            999 V2000
    1.1348   -0.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3402    0.1036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9761    0.6292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    1.1061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355    1.7419    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.3771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3465    0.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4461   -0.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -0.5555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7604   -1.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6210    0.1735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4459    0.1602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9163    0.7928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086   -0.5808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2628   -1.1994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5890   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300   -0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975    0.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4209    0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348    1.0358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4544    1.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134    0.9406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7913    1.7620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538    1.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    2.1267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3196    0.4058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9383   -0.1400    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4983    0.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407   -0.5368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    0.9621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3272    1.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    2.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  0  0  0  0
 10  2  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  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
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 21 19  1  0  0  0  0
 21 22  1  6  0  0  0
 23 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 22 26  2  0  0  0  0
 27 21  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 12 30  1  1  0  0  0
 12 31  1  0  0  0  0
 31 25  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@@]3(O)C(=O)[C@]4([H])[C@H](C)C=C[C@](O)([C@@]3([H])[C@]1([H])[C@@]1(O)C=C[C@@H](C)[C@@H](C2=O)[C@@]1([H])O)[C@]4([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-7-3-5-18(25)11-13(12(21)9(7)15(18)22)28-20(27)14(11)19(26)6-4-8(2)10(16(19)23)17(20)24/h3-11,13-16,22-23,25-27H,1-2H3/t7-,8-,9+,10-,11-,13-,14-,15-,16-,18+,19+,20-/m1/s1

> <INCHI_KEY>
NFTXVVKWHYQZLB-ADENSFJQSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.02752014572184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4S,7R,8R,10R,12R,14R,15R,18R,19R)-1,4,10,18,19-pentahydroxy-7,15-dimethyl-11-oxapentacyclo[12.3.1.1^{4,8}.0^{2,12}.0^{3,10}]nonadeca-5,16-diene-9,13-dione

> <JCHEM_LOGP>
-0.7608676693333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.680498647159347

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.001939636455562

> <JCHEM_PKA_STRONGEST_BASIC>
-3.447091493730452

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
95.69149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4S,7R,8R,10R,12R,14R,15R,18R,19R)-1,4,10,18,19-pentahydroxy-7,15-dimethyl-11-oxapentacyclo[12.3.1.1^{4,8}.0^{2,12}.0^{3,10}]nonadeca-5,16-diene-9,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-24         0                                  
HETATM    1  O   UNK     0       2.118  -1.298   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.502   0.193   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0       3.689   1.175   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0       1.607   2.065   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       0.626   3.252   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       0.886   0.704   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.647   0.849   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.339  -0.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.699  -1.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.171  -1.037   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.153  -2.224   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.893   0.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.432   0.299   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       5.444   1.480   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       7.109  -1.084   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.091  -2.239   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.566  -1.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.949  -0.906   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.449   0.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.986   0.647   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.772   1.934   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.315   2.433   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.932   1.756   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       7.077   3.289   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       5.701   2.681   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.219   3.970   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.063   0.757   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       9.218  -0.261   0.000  0.00  0.00           H+0
HETATM   29  O   UNK     0       6.530   0.903   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       5.676  -1.002   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       4.440   1.796   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.344   3.333   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.080   2.517   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.225   4.050   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6   33                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   30   31                                             
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   31                                                       
CONECT   26   22                                                            
CONECT   27   21   15   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   12                                                            
CONECT   31   12   25   32   33                                             
CONECT   32   31                                                            
CONECT   33   31    4   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(1S,2S,3R,4S,7R,8R,10R,12R,14R,15R,18R,19R)-1,4,10,18,19-pentahydroxy-7,15-dimethyl-11-oxapentacyclo[12.3.1.1^{4,8}.0^{2,12}.0^{3,10}]nonadeca-5,16-diene-9,13-dione

Traditional Name

(1S,2S,3R,4S,7R,8R,10R,12R,14R,15R,18R,19R)-1,4,10,18,19-pentahydroxy-7,15-dimethyl-11-oxapentacyclo[12.3.1.1^{4,8}.0^{2,12}.0^{3,10}]nonadeca-5,16-diene-9,13-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@@]3(O)C(=O)[C@]4([H])[C@H](C)C=C[C@](O)([C@@]3([H])[C@]1([H])[C@@]1(O)C=C[C@@H](C)[C@@H](C2=O)[C@@]1([H])O)[C@]4([H])O

InChI Identifier

InChI=1S/C20H24O8/c1-7-3-5-18(25)11-13(12(21)9(7)15(18)22)28-20(27)14(11)19(26)6-4-8(2)10(16(19)23)17(20)24/h3-11,13-16,22-23,25-27H,1-2H3/t7-,8-,9+,10-,11-,13-,14-,15-,16-,18+,19+,20-/m1/s1

InChI Key

NFTXVVKWHYQZLB-ADENSFJQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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	-0.76	ChemAxon
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	95.69 m³·mol⁻¹	ChemAxon
Polarizability	38.03 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for paraphaeoketone C (NP0332422)

MOL for NP0332422 (paraphaeoketone C)

3D MOL for NP0332422 (paraphaeoketone C)

3D SDF for NP0332422 (paraphaeoketone C)

3D-SDF for NP0332422 (paraphaeoketone C)

PDB for NP0332422 (paraphaeoketone C)

3D PDB for NP0332422 (paraphaeoketone C)

SMILES for NP0332422 (paraphaeoketone C)

INCHI for NP0332422 (paraphaeoketone C)

Structure for NP0332422 (paraphaeoketone C)

3D Structure for NP0332422 (paraphaeoketone C)