NP-MRD: Showing NP-Card for paraphaeoketone A acetonide (NP0332423)

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Record Information

Version

2.0

Created at

2024-01-23 12:01:21 UTC

Updated at

2024-09-03 04:19:07 UTC

NP-MRD ID

NP0332423

Natural Product DOI

https://doi.org/10.57994/1642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

paraphaeoketone A acetonide

Description

Paraphaeoketone A acetonide belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring. Based on a literature review very few articles have been published on paraphaeoketone A acetonide.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232412012D          

 18 21  0  0  1  0            999 V2000
    5.0901    1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333    0.6199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6605   -0.2429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7868   -0.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9499   -0.6484    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4821   -1.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860   -0.9809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4778   -1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1096   -0.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9132    0.2284    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1138    0.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822   -0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866    0.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710   -0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958   -0.7710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    0.6697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0566   -0.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8266    0.2317    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
  7  6  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  3  9  1  6  0  0  0
 10  5  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 15  1  0  0  0  0
 16 10  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  6  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H]2C[C@@]34OC(C)(C)O[C@@H]3[C@@H]1C(=O)[C@@](C)(O2)O4

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O5/c1-6-7-5-13-10(16-11(2,3)17-13)8(6)9(14)12(4,15-7)18-13/h6-8,10H,5H2,1-4H3/t6-,7-,8+,10-,12+,13+/m1/s1

> <INCHI_KEY>
IUICXKOVHVNXSG-KYJMXIKRSA-N

> <FORMULA>
C13H18O5

> <MOLECULAR_WEIGHT>
254.282

> <EXACT_MASS>
254.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.60944901150214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6R,7S,8R,10S)-3,3,7,10-tetramethyl-2,4,9,11-tetraoxatetracyclo[6.3.1.1^{6,10}.0^{1,5}]tridecan-13-one

> <JCHEM_LOGP>
2.2369879193333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.210902221848464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.882758099491775

> <JCHEM_POLAR_SURFACE_AREA>
53.99

> <JCHEM_REFRACTIVITY>
60.51610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R,7S,8R,10S)-3,3,7,10-tetramethyl-2,4,9,11-tetraoxatetracyclo[6.3.1.1^{6,10}.0^{1,5}]tridecan-13-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  C   UNK     0       9.502   2.294   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.462   1.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.700  -0.453   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.069  -1.096   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.506  -1.210   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.500  -2.516   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.001  -1.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.359  -3.329   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.538  -1.768   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.438   0.426   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.946   0.972   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.953  -0.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.842   0.845   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.813  -1.255   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.912  -1.439   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.843   1.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.572  -0.120   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.010   0.432   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   15                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7    3                                                       
CONECT   10    5   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    5                                                       
CONECT   16   10    2   17                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O₅

Average Mass

254.2820 Da

Monoisotopic Mass

254.11542 Da

IUPAC Name

(1S,5R,6R,7S,8R,10S)-3,3,7,10-tetramethyl-2,4,9,11-tetraoxatetracyclo[6.3.1.1^{6,10}.0^{1,5}]tridecan-13-one

Traditional Name

(1S,5R,6R,7S,8R,10S)-3,3,7,10-tetramethyl-2,4,9,11-tetraoxatetracyclo[6.3.1.1^{6,10}.0^{1,5}]tridecan-13-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H]2C[C@@]34OC(C)(C)O[C@@H]3[C@@H]1C(=O)[C@@](C)(O2)O4

InChI Identifier

InChI=1S/C13H18O5/c1-6-7-5-13-10(16-11(2,3)17-13)8(6)9(14)12(4,15-7)18-13/h6-8,10H,5H2,1-4H3/t6-,7-,8+,10-,12+,13+/m1/s1

InChI Key

IUICXKOVHVNXSG-KYJMXIKRSA-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 dioxolopyrans. These are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxolopyrans

Sub Class

Not Available

Direct Parent

Dioxolopyrans

Alternative Parents

Substituents

Dioxolopyran
Ketal
Oxane
Meta-dioxane
Meta-dioxolane
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.24	ChemAxon
pKa (Strongest Acidic)	18.21	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	60.52 m³·mol⁻¹	ChemAxon
Polarizability	25.61 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 A acetonide (NP0332423)

MOL for NP0332423 (paraphaeoketone A acetonide)

3D MOL for NP0332423 (paraphaeoketone A acetonide)

3D SDF for NP0332423 (paraphaeoketone A acetonide)

3D-SDF for NP0332423 (paraphaeoketone A acetonide)

PDB for NP0332423 (paraphaeoketone A acetonide)

3D PDB for NP0332423 (paraphaeoketone A acetonide)

SMILES for NP0332423 (paraphaeoketone A acetonide)

INCHI for NP0332423 (paraphaeoketone A acetonide)

Structure for NP0332423 (paraphaeoketone A acetonide)

3D Structure for NP0332423 (paraphaeoketone A acetonide)