NP-MRD: Showing NP-Card for paraphaeoketone B diacetate (NP0332426)

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Record Information

Version

2.0

Created at

2024-01-23 12:02:12 UTC

Updated at

2024-09-03 04:19:08 UTC

NP-MRD ID

NP0332426

Natural Product DOI

https://doi.org/10.57994/1645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeoketone B diacetate

Description

Paraphaeoketone B diacetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review very few articles have been published on paraphaeoketone B diacetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232412022D          

 22 23  0  0  1  0            999 V2000
   -0.1827   -0.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -0.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9905   -0.5124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9679   -1.3371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3275   -0.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    0.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    1.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    1.6426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2791    1.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    0.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836    0.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313    0.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2464    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -0.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0981    2.5450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    0.5725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5754    0.5498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863    0.7241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    1.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4902    1.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819    2.2139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  1  6  0  0  0
 17  9  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  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
M  END
> <DATABASE_ID>
NP0332426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@H](C)C=C[C@](O)(C=C(OC(C)=O)C1=O)[C@]2([H])OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O6/c1-7-4-5-14(18)6-10(19-8(2)15)12(17)11(7)13(14)20-9(3)16/h4-7,11,13,18H,1-3H3/t7-,11+,13-,14+/m1/s1

> <INCHI_KEY>
WGERPOMHGBALEL-SHNOVCJGSA-N

> <FORMULA>
C14H16O6

> <MOLECULAR_WEIGHT>
280.276

> <EXACT_MASS>
280.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.239069045523966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6R,9R)-3-(acetyloxy)-1-hydroxy-6-methyl-4-oxobicyclo[3.3.1]nona-2,7-dien-9-yl acetate

> <JCHEM_LOGP>
0.1328689040000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.930225451902484

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.860253315949695

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7347251636151637

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
69.77980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R,9R)-3-(acetyloxy)-1-hydroxy-6-methyl-4-oxobicyclo[3.3.1]nona-2,7-dien-9-yl acetate

> <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      -0.341  -1.830   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.443  -0.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.849  -0.957   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       1.807  -2.496   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       3.287  -0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.345  -1.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.916   1.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.365   2.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.959   3.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.521   2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.489   0.844   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.463   1.016   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.858   0.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.193   0.975   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.856  -1.333   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.050   4.751   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.401   1.069   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       2.941   1.026   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0      -0.348   1.352   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.243   2.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.782   2.709   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.526   4.133   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5   17                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16   17                                             
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
CONECT   17    9    3   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
Paraphaeoketone b diacetic acid	Generator

Chemical Formula

C₁₄H₁₆O₆

Average Mass

280.2760 Da

Monoisotopic Mass

280.09469 Da

IUPAC Name

(1S,5R,6R,9R)-3-(acetyloxy)-1-hydroxy-6-methyl-4-oxobicyclo[3.3.1]nona-2,7-dien-9-yl acetate

Traditional Name

(1S,5R,6R,9R)-3-(acetyloxy)-1-hydroxy-6-methyl-4-oxobicyclo[3.3.1]nona-2,7-dien-9-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@H](C)C=C[C@](O)(C=C(OC(C)=O)C1=O)[C@]2([H])OC(C)=O

InChI Identifier

InChI=1S/C14H16O6/c1-7-4-5-14(18)6-10(19-8(2)15)12(17)11(7)13(14)20-9(3)16/h4-7,11,13,18H,1-3H3/t7-,11+,13-,14+/m1/s1

InChI Key

WGERPOMHGBALEL-SHNOVCJGSA-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	¹H NMR Spectrum (1D, 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 fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Cyclohexenone
Alpha-branched alpha,beta-unsaturated-ketone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Enol ester
Acryloyl-group
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	0.13	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.78 m³·mol⁻¹	ChemAxon
Polarizability	27.24 Å³	ChemAxon
Number of Rings	2	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 diacetate (NP0332426)

MOL for NP0332426 (paraphaeoketone B diacetate)

3D MOL for NP0332426 (paraphaeoketone B diacetate)

3D SDF for NP0332426 (paraphaeoketone B diacetate)

3D-SDF for NP0332426 (paraphaeoketone B diacetate)

PDB for NP0332426 (paraphaeoketone B diacetate)

3D PDB for NP0332426 (paraphaeoketone B diacetate)

SMILES for NP0332426 (paraphaeoketone B diacetate)

INCHI for NP0332426 (paraphaeoketone B diacetate)

Structure for NP0332426 (paraphaeoketone B diacetate)

3D Structure for NP0332426 (paraphaeoketone B diacetate)