NP-MRD: Showing NP-Card for Acetoxytongalide B (NP0333181)

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Record Information

Version

2.0

Created at

2024-05-12 05:27:38 UTC

Updated at

2024-09-03 04:21:30 UTC

NP-MRD ID

NP0333181

Natural Product DOI

https://doi.org/10.57994/2506

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetoxytongalide B

Description

Acetoxytongalide B belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Acetoxytongalide B was first documented in 2022 (PMID: 35771948). Based on a literature review very few articles have been published on Acetoxytongalide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242308042D          

 18 18  0  0  1  0            999 V2000
   -1.9862   -4.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2016   -4.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -3.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -3.0278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2486   -2.6153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486   -1.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631   -1.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5342   -1.3778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -2.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -1.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -1.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333   -4.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179   -4.0828    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217   -5.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -5.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373   -4.6808    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2079   -5.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9467   -5.1224    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
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](OC(C)=O)C1=C(Br)C(O)(CBr)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14Br2O5/c1-3-4-7(17-6(2)14)8-9(13)11(16,5-12)18-10(8)15/h7,16H,3-5H2,1-2H3/t7-,11?/m1/s1

> <INCHI_KEY>
BYOVBSWJUBIXJV-DKSCNQEISA-N

> <FORMULA>
C11H14Br2O5

> <MOLECULAR_WEIGHT>
386.036

> <EXACT_MASS>
383.9208

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.77312584930678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[4-bromo-5-(bromomethyl)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]butyl acetate

> <JCHEM_LOGP>
2.597725599333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.009017101954946

> <JCHEM_PKA_STRONGEST_BASIC>
-4.981855919604906

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
71.07300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[4-bromo-5-(bromomethyl)-5-hydroxy-2-oxofuran-3-yl]butyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -3.708  -7.621   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.243  -8.097   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.997  -7.192   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.997  -5.652   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.331  -4.882   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.331  -3.342   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.664  -2.572   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.997  -2.572   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.337  -4.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.337  -3.342   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.670  -2.572   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.249  -8.097   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       1.713  -7.621   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0      -0.227  -9.562   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.279  -9.882   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       2.310  -8.737   0.000  0.00  0.00          Br+0
HETATM   17  O   UNK     0      -0.388 -11.093   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.767  -9.562   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    3   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17   18                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-[4-Bromo-5-(bromomethyl)-5-hydroxy-2-oxofuran-3-yl]butyl acetic acid	Generator

Chemical Formula

C₁₁H₁₄Br₂O₅

Average Mass

386.0360 Da

Monoisotopic Mass

383.92080 Da

IUPAC Name

(1R)-1-[4-bromo-5-(bromomethyl)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]butyl acetate

Traditional Name

(1R)-1-[4-bromo-5-(bromomethyl)-5-hydroxy-2-oxofuran-3-yl]butyl acetate

CAS Registry Number

Not Available

SMILES

CCC[C@@H](OC(C)=O)C1=C(Br)C(O)(CBr)OC1=O

InChI Identifier

InChI=1S/C11H14Br2O5/c1-3-4-7(17-6(2)14)8-9(13)11(16,5-12)18-10(8)15/h7,16H,3-5H2,1-2H3/t7-,11?/m1/s1

InChI Key

BYOVBSWJUBIXJV-DKSCNQEISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp.		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Hemiketal
Dicarboxylic acid or derivatives
2-furanone
Vinylogous halide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Bromoalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl bromide
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.6	ChemAxon
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.07 m³·mol⁻¹	ChemAxon
Polarizability	29.77 Å³	ChemAxon
Number of Rings	1	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

168290327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bracegirdle J, Kennedy SJ, Shan C, Wojtas L, Shaw LN, Amsler CD, McClintock JB, Baker BJ: Tongalides, Halogenated Butenolides from an Antarctic Delisea sp. Rhodophyte. J Nat Prod. 2022 Jul 22;85(7):1886-1891. doi: 10.1021/acs.jnatprod.2c00344. Epub 2022 Jun 30. [PubMed:35771948 ]

Showing NP-Card for Acetoxytongalide B (NP0333181)

MOL for NP0333181 (Acetoxytongalide B)

3D MOL for NP0333181 (Acetoxytongalide B)

3D SDF for NP0333181 (Acetoxytongalide B)

3D-SDF for NP0333181 (Acetoxytongalide B)

PDB for NP0333181 (Acetoxytongalide B)

3D PDB for NP0333181 (Acetoxytongalide B)

SMILES for NP0333181 (Acetoxytongalide B)

INCHI for NP0333181 (Acetoxytongalide B)

Structure for NP0333181 (Acetoxytongalide B)

3D Structure for NP0333181 (Acetoxytongalide B)