NP-MRD: Showing NP-Card for Weizhouochrone B (NP0333197)

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Record Information

Version

2.0

Created at

2024-05-12 09:35:58 UTC

Updated at

2024-09-03 04:21:32 UTC

NP-MRD ID

NP0333197

Natural Product DOI

https://doi.org/10.57994/2522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Weizhouochrone B

Description

Weizhouochrone B belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Weizhouochrone B was first documented in 2022 (PMID: 35792821). Based on a literature review very few articles have been published on Weizhouochrone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242312122D          

 32 36  0  0  1  0            999 V2000
    3.7204    2.2809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561    1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6001   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1782   -0.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -0.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9575   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8208    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990    0.1704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5633   -0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    0.9433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7043    1.6614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.6546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5133    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405    1.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6262   -0.1183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0322   -0.8364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804   -0.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161   -1.4559    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  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  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  4  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15  2  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  2  0  0  0  0
 18 27  1  0  0  0  0
 17 28  1  6  0  0  0
 29 17  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END


  Mrv2104 01242312122D          

 32 36  0  0  1  0            999 V2000
    3.7204    2.2809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561    1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6001   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1782   -0.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -0.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9575   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8208    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2427    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990    0.1704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5633   -0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    0.9433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7043    1.6614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.6546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5133    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    1.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405    1.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    2.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6262   -0.1183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0322   -0.8364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804   -0.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161   -1.4559    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  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  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  4  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15  2  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  2  0  0  0  0
 18 27  1  0  0  0  0
 17 28  1  6  0  0  0
 29 17  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C(=O)C3=C(C=C(C=C3C)C(C)C)[C@@]1(C)[C@@]1([H])C(=O)C3=C(C=C(C=C3C)C(C)C)[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O2/c1-13(2)17-9-15(5)21-19(11-17)27(7)25(23(21)29)28(8)20-12-18(14(3)4)10-16(6)22(20)24(30)26(27)28/h9-14,25-26H,1-8H3/t25-,26+,27+,28-/m0/s1

> <INCHI_KEY>
LVSPGEUBAKEBOC-HFLBTKGNSA-N

> <FORMULA>
C28H32O2

> <MOLECULAR_WEIGHT>
400.562

> <EXACT_MASS>
400.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.59849579806776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2s,10S,11R)-2,7,11,16-tetramethyl-5,14-bis(propan-2-yl)pentacyclo[9.7.0.0^{2,10}.0^{3,8}.0^{12,17}]octadeca-3(8),4,6,12(17),13,15-hexaene-9,18-dione

> <JCHEM_LOGP>
6.744351610666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.953122939848493

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.305276075678133

> <JCHEM_PKA_STRONGEST_BASIC>
-7.2552922509280355

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
123.10339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2s,10S,11R)-5,14-diisopropyl-2,7,11,16-tetramethylpentacyclo[9.7.0.0^{2,10}.0^{3,8}.0^{12,17}]octadeca-3(8),4,6,12(17),13,15-hexaene-9,18-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  O   UNK     0       6.945   4.258   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.011   2.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.295   1.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.883   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.962  -0.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.454  -0.329   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.533  -1.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.024  -1.042   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.121  -2.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.865   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.786   2.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.198   3.738   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.345   0.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.651  -1.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.806   1.761   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.048   3.101   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       4.363   1.222   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.825   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.413  -0.329   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.922  -0.714   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.510  -2.198   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.157   0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.255   1.869   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.824   2.967   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.316   2.582   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.412   4.451   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.746   2.254   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.057   2.731   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.902  -0.221   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       5.660  -1.561   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       3.697  -1.179   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.763  -2.718   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13    4   14   15   29                                             
CONECT   14   13                                                            
CONECT   15   13    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   28   29                                             
CONECT   18   17   19   27                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   18                                                       
CONECT   28   17                                                            
CONECT   29   17   13   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   19   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₂

Average Mass

400.5620 Da

Monoisotopic Mass

400.24023 Da

IUPAC Name

(1R,2s,10S,11R)-2,7,11,16-tetramethyl-5,14-bis(propan-2-yl)pentacyclo[9.7.0.0^{2,10}.0^{3,8}.0^{12,17}]octadeca-3(8),4,6,12(17),13,15-hexaene-9,18-dione

Traditional Name

(1R,2s,10S,11R)-5,14-diisopropyl-2,7,11,16-tetramethylpentacyclo[9.7.0.0^{2,10}.0^{3,8}.0^{12,17}]octadeca-3(8),4,6,12(17),13,15-hexaene-9,18-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12C(=O)C3=C(C=C(C=C3C)C(C)C)[C@@]1(C)[C@@]1([H])C(=O)C3=C(C=C(C=C3C)C(C)C)[C@@]21C

InChI Identifier

InChI=1S/C28H32O2/c1-13(2)17-9-15(5)21-19(11-17)27(7)25(23(21)29)28(8)20-12-18(14(3)4)10-16(6)22(20)24(30)26(27)28/h9-14,25-26H,1-8H3/t25-,26+,27+,28-/m0/s1

InChI Key

LVSPGEUBAKEBOC-HFLBTKGNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	xli@fmp-berlin.de	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-12	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anthogorgia ochracea		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Indanone
Indane
Aryl alkyl ketone
Aryl ketone
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	6.74	ChemAxon
pKa (Strongest Acidic)	15.31	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	123.1 m³·mol⁻¹	ChemAxon
Polarizability	46.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li XL, Ru T, Navarro-Vazquez A, Lindemann P, Nazare M, Li XW, Guo YW, Sun H: Weizhouochrones: Gorgonian-Derived Symmetric Dimers and Their Structure Elucidation Using Anisotropic NMR Combined with DP4+ Probability and CASE-3D. J Nat Prod. 2022 Jul 22;85(7):1730-1737. doi: 10.1021/acs.jnatprod.2c00257. Epub 2022 Jul 6. [PubMed:35792821 ]
DOI: 10.1021/acs.jnatprod.2c00257

Showing NP-Card for Weizhouochrone B (NP0333197)

MOL for NP0333197 (Weizhouochrone B)

3D MOL for NP0333197 (Weizhouochrone B)

3D SDF for NP0333197 (Weizhouochrone B)

3D-SDF for NP0333197 (Weizhouochrone B)

PDB for NP0333197 (Weizhouochrone B)

3D PDB for NP0333197 (Weizhouochrone B)

SMILES for NP0333197 (Weizhouochrone B)

INCHI for NP0333197 (Weizhouochrone B)

Structure for NP0333197 (Weizhouochrone B)

3D Structure for NP0333197 (Weizhouochrone B)