NP-MRD: Showing NP-Card for paraphaeoketone B (NP0332424)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-01-23 12:01:37 UTC

Updated at

2024-09-03 04:19:07 UTC

NP-MRD ID

NP0332424

Natural Product DOI

https://doi.org/10.57994/1643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeoketone B

Description

Paraphaeoketone B belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on paraphaeoketone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232412012D          

 32 34  0  0  1  0            999 V2000
   -1.0152   -0.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.1379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4773   -0.1379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783    0.9400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783    1.7650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405    0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4238    1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -1.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783   -2.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9997   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -0.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    1.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -0.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -0.1379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0510   -0.1379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954    0.9400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7332    0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1499    1.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954    1.7650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2576    0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8410    1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2576   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954   -1.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4954   -2.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -0.1379    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
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  1  0  0  0
 20 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END


  Mrv2104 01232412012D          

 32 34  0  0  1  0            999 V2000
   -1.0152   -0.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.1379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4773   -0.1379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783    0.9400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783    1.7650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405    0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4238    1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -1.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783   -2.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9997   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247   -0.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    1.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -0.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -0.1379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0510   -0.1379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954    0.9400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7332    0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1499    1.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954    1.7650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2576    0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8410    1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2576   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4954   -1.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4954   -2.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -0.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -0.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5925   -0.1379    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
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  1  0  0  0
 20 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O)[C@@]2([H])[C@H](C)C=C[C@]1(O)CC(=O)C2=O.[H][C@@]1(O)[C@@]2([H])[C@H](C)C=C[C@]1(O)C=C(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/2C10H12O4/c2*1-5-2-3-10(14)4-6(11)8(12)7(5)9(10)13/h2-3,5,7,9,13-14H,4H2,1H3;2-5,7,9,11,13-14H,1H3/t2*5-,7+,9-,10+/m11/s1

> <INCHI_KEY>
WNHCCVJBAUIOON-ISWZLIKRSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
18.827098130314404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,8R,9R)-5,9-dihydroxy-8-methylbicyclo[3.3.1]non-6-ene-2,3-dione; (1R,5S,8R,9R)-3,5,9-trihydroxy-8-methylbicyclo[3.3.1]nona-3,6-dien-2-one

> <JCHEM_LOGP>
-0.21908280233333316

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.249990014654793

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.571379841583326

> <JCHEM_PKA_STRONGEST_BASIC>
-3.475096186828013

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
51.47680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,8R,9R)-5,9-dihydroxy-8-methylbicyclo[3.3.1]non-6-ene-2,3-dione; (1R,5S,8R,9R)-3,5,9-trihydroxy-8-methylbicyclo[3.3.1]nona-3,6-dien-2-one

> <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      -1.895  -1.163   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.649  -0.257   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0       0.891  -0.257   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      -0.146   1.755   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0      -0.146   3.295   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -1.569   1.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.658   2.254   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.158  -0.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.569  -1.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.146  -2.269   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.146  -3.809   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.277  -1.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.866  -0.257   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.406  -0.257   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.277   1.165   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.366   2.254   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.509  -1.163   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.755  -0.257   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      11.295  -0.257   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      10.258   1.755   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.835   1.165   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.746   2.254   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      10.258   3.295   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      11.681   1.165   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.770   2.254   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.270  -0.257   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.681  -1.680   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.258  -2.269   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.258  -3.809   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.835  -1.680   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.246  -0.257   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.706  -0.257   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   15                                             
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                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4   16                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   17   19   20   28                                             
CONECT   19   18                                                            
CONECT   20   18   21   23   24                                             
CONECT   21   20   22   31                                                  
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   18   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   21   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(1R,5R,8R,9R)-5,9-dihydroxy-8-methylbicyclo[3.3.1]non-6-ene-2,3-dione; (1R,5S,8R,9R)-3,5,9-trihydroxy-8-methylbicyclo[3.3.1]nona-3,6-dien-2-one

Traditional Name

(1R,5R,8R,9R)-5,9-dihydroxy-8-methylbicyclo[3.3.1]non-6-ene-2,3-dione; (1R,5S,8R,9R)-3,5,9-trihydroxy-8-methylbicyclo[3.3.1]nona-3,6-dien-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)[C@@]2([H])[C@H](C)C=C[C@]1(O)CC(=O)C2=O.[H][C@@]1(O)[C@@]2([H])[C@H](C)C=C[C@]1(O)C=C(O)C2=O

InChI Identifier

InChI=1S/2C10H12O4/c2*1-5-2-3-10(14)4-6(11)8(12)7(5)9(10)13/h2-3,5,7,9,13-14H,4H2,1H3;2-5,7,9,11,13-14H,1H3/t2*5-,7+,9-,10+/m11/s1

InChI Key

WNHCCVJBAUIOON-ISWZLIKRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	h22ga205@hirosaki-u.ac.jp	Hirosaki University	Ryuhi Kanehara	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, 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

Description

This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
B'-hydroxy-alpha,beta-unsaturated-ketone
Alpha-branched alpha,beta-unsaturated-ketone
Beta-hydroxy ketone
Alpha-diketone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Cyclic alcohol
Alpha-hydroxy ketone
Acryloyl-group
Secondary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Not Available

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	-0.22	ChemAxon
pKa (Strongest Acidic)	8.57	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51.48 m³·mol⁻¹	ChemAxon
Polarizability	18.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

Showing NP-Card for paraphaeoketone B (NP0332424)

MOL for NP0332424 (paraphaeoketone B)

3D MOL for NP0332424 (paraphaeoketone B)

3D SDF for NP0332424 (paraphaeoketone B)

3D-SDF for NP0332424 (paraphaeoketone B)

PDB for NP0332424 (paraphaeoketone B)

3D PDB for NP0332424 (paraphaeoketone B)

SMILES for NP0332424 (paraphaeoketone B)

INCHI for NP0332424 (paraphaeoketone B)

Structure for NP0332424 (paraphaeoketone B)

3D Structure for NP0332424 (paraphaeoketone B)