NP-MRD: Showing NP-Card for (5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one (NP0205676)

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Record Information

Version

2.0

Created at

2022-09-05 01:38:17 UTC

Updated at

2022-09-05 01:38:18 UTC

NP-MRD ID

NP0205676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one

Description

CHEMBL526844 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. (5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one is found in Delisea pulchra. Based on a literature review very few articles have been published on CHEMBL526844.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.3959    1.0290    0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5626   -0.1589    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1079    0.1891    0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.9791   -0.1159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4683   -1.1947   -1.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -0.6407    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238   -0.5833   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985   -0.9129   -2.6001 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4216   -0.2157   -0.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4206   -1.3196   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2924   -1.0919    0.6051 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    1.0025   -0.6030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278    1.7540   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -0.0822    1.2947 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -0.3284    1.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0656   -0.3026    2.5468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3630    0.6474    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    1.6452    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6397    1.5981   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7925   -1.0717    0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6526   -0.3662   -1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844    1.0895   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0323    0.2875    1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -1.9095    0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7965   -0.3922   -1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347   -2.2552    0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5225   -1.4930   -1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    2.7391   -0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    1.2707   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080    2.0459    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  6
 12 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  2  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  1
  5 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
M  END


  Mrv1652309052203382D          

 16 16  0  0  1  0            999 V2000
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0205676

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14BrIO4/c1-3-4-6(13)7-8(11)10(5-12,15-2)16-9(7)14/h6,13H,3-5H2,1-2H3/t6-,10+/m1/s1

> <INCHI_KEY>
YRYRVZXFQIQXET-LDWIPMOCSA-N

> <FORMULA>
C10H14BrIO4

> <MOLECULAR_WEIGHT>
405.026

> <EXACT_MASS>
403.91202

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
29.094034889969997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-4-bromo-3-[(1R)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxy-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.8453954910000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.249450765221102

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1270902352922905

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
72.1858

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-4-bromo-3-[(1R)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0      -1.651   1.651   0.000  0.00  0.00          Br+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM   11  I   UNK     0      -1.477   2.904   0.000  0.00  0.00           I+0
HETATM   12  O   UNK     0       2.090   3.224   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.597   2.904   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12   14                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄BrIO₄

Average Mass

405.0260 Da

Monoisotopic Mass

403.91202 Da

IUPAC Name

(5R)-4-bromo-3-[(1R)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxy-2,5-dihydrofuran-2-one

Traditional Name

(5R)-4-bromo-3-[(1R)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H14BrIO4/c1-3-4-6(13)7-8(11)10(5-12,15-2)16-9(7)14/h6,13H,3-5H2,1-2H3/t6-,10+/m1/s1

InChI Key

YRYRVZXFQIQXET-LDWIPMOCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delisea pulchra	LOTUS Database	35616633

Chemical Taxonomy

Description

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
2-furanone
Dihydrofuran
Enoate ester
Vinylogous halide
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Bromoalkene
Monocarboxylic acid or derivatives
Haloalkene
Vinyl bromide
Vinyl halide
Organoheterocyclic compound
Alkyl halide
Alkyl iodide
Organohalogen compound
Organobromide
Organoiodide
Organic oxide
Carbonyl group
Alcohol
Hydrocarbon derivative
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	2.85	ChemAxon
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.19 m³·mol⁻¹	ChemAxon
Polarizability	29.09 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

10475472

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21773478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one (NP0205676)

MOL for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

3D MOL for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

3D SDF for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

3D-SDF for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

PDB for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

3D PDB for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

SMILES for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

INCHI for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

Structure for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)

3D Structure for NP0205676 ((5r)-4-bromo-3-[(1r)-1-hydroxybutyl]-5-(iodomethyl)-5-methoxyfuran-2-one)