NP-MRD: Showing NP-Card for paraphaeoketone A (NP0332425)

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Record Information

Version

2.0

Created at

2024-01-23 12:01:54 UTC

Updated at

2024-09-03 04:19:07 UTC

NP-MRD ID

NP0332425

Natural Product DOI

https://doi.org/10.57994/1644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeoketone A

Description

Paraphaeoketone A belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Based on a literature review very few articles have been published on paraphaeoketone A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232412012D          

 15 17  0  0  1  0            999 V2000
   -0.4806   -2.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163   -2.0322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8517   -1.6585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5873   -2.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -1.2419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8344   -1.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8517   -2.4835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8517   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -0.1208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5657   -0.4945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1375   -0.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -1.2419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3012   -1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -2.4406    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  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5 14  1  0  0  0  0
  3  8  1  1  0  0  0
 13 14  1  1  0  0  0
 10  9  1  0  0  0  0
 10  7  1  6  0  0  0
 11 10  1  0  0  0  0
 11 12  1  6  0  0  0
  2 13  1  0  0  0  0
 13 11  1  0  0  0  0
  3  9  1  0  0  0  0
  5  7  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H]2C[C@]3(O)O[C@](C)(O2)C(=O)[C@H]1[C@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O5/c1-4-5-3-10(13)8(12)6(4)7(11)9(2,14-5)15-10/h4-6,8,12-13H,3H2,1-2H3/t4-,5-,6+,8-,9+,10+/m1/s1

> <INCHI_KEY>
MFSNDTDWPICOOL-GESHZNSBSA-N

> <FORMULA>
C10H14O5

> <MOLECULAR_WEIGHT>
214.217

> <EXACT_MASS>
214.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.347881962614682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5R,6S,7R,8R)-1,8-dihydroxy-3,6-dimethyl-2,4-dioxatricyclo[3.3.1.1^{3,7}]decan-10-one

> <JCHEM_LOGP>
0.5345633036666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.662951281924707

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.946634231341392

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7413551332457176

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
48.3091

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,6S,7R,8R)-1,8-dihydroxy-3,6-dimethyl-2,4-dioxatricyclo[3.3.1.1^{3,7}]decan-10-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      -0.897  -4.857   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.217  -3.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.590  -3.096   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.963  -3.793   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.802  -2.318   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.291  -2.712   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.802  -0.923   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.590  -4.636   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.590  -1.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.429  -0.225   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.056  -0.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.257  -0.118   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.056  -2.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.429  -3.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.429  -4.556   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    8    9                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5   10                                                       
CONECT    8    3                                                            
CONECT    9    3   10                                                       
CONECT   10    9    7   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₅

Average Mass

214.2170 Da

Monoisotopic Mass

214.08412 Da

IUPAC Name

(1S,3S,5R,6S,7R,8R)-1,8-dihydroxy-3,6-dimethyl-2,4-dioxatricyclo[3.3.1.1^{3,7}]decan-10-one

Traditional Name

(1S,3S,5R,6S,7R,8R)-1,8-dihydroxy-3,6-dimethyl-2,4-dioxatricyclo[3.3.1.1^{3,7}]decan-10-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H]2C[C@]3(O)O[C@](C)(O2)C(=O)[C@H]1[C@H]3O

InChI Identifier

InChI=1S/C10H14O5/c1-4-5-3-10(13)8(12)6(4)7(11)9(2,14-5)15-10/h4-6,8,12-13H,3H2,1-2H3/t4-,5-,6+,8-,9+,10+/m1/s1

InChI Key

MFSNDTDWPICOOL-GESHZNSBSA-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
1D NMR	¹H NMR Spectrum (1D, 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
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
NOESY 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	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 ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Oxane
Hemiketal
Beta-hydroxy ketone
Meta-dioxane
Cyclic alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.53	ChemAxon
pKa (Strongest Acidic)	10.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	48.31 m³·mol⁻¹	ChemAxon
Polarizability	20.35 Å³	ChemAxon
Number of Rings	3	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

Not Available

Showing NP-Card for paraphaeoketone A (NP0332425)

MOL for NP0332425 (paraphaeoketone A)

3D MOL for NP0332425 (paraphaeoketone A)

3D SDF for NP0332425 (paraphaeoketone A)

3D-SDF for NP0332425 (paraphaeoketone A)

PDB for NP0332425 (paraphaeoketone A)

3D PDB for NP0332425 (paraphaeoketone A)

SMILES for NP0332425 (paraphaeoketone A)

INCHI for NP0332425 (paraphaeoketone A)

Structure for NP0332425 (paraphaeoketone A)

3D Structure for NP0332425 (paraphaeoketone A)