NP-MRD: Showing NP-Card for (1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol (NP0260361)

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Record Information

Version

2.0

Created at

2022-09-08 02:30:32 UTC

Updated at

2022-09-08 02:30:32 UTC

NP-MRD ID

NP0260361

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol

Description

(1R,3E)-1-[(2R,4S,5S)-4-bromo-5-{[(2R,3R)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. (1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol is found in Laurencia nipponica. Based on a literature review very few articles have been published on (1R,3E)-1-[(2R,4S,5S)-4-bromo-5-{[(2R,3R)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    7.8361   -0.8982    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6576   -0.6375    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393   -0.3336    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -1.3163    0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9359   -1.1686    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386    0.2172    0.5035 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8209    0.6306   -0.7841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9063    0.2639    0.6105 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4809    1.6546    0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439    1.4094   -1.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4842    2.7654   -1.4940 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8319    0.0288   -0.7833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7375   -0.0338    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.4899    0.2419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6176    1.0736   -0.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.2555   -0.8296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2688   -0.7375   -0.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6612   -0.3187    0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3779   -0.5928   -0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8671   -1.1219    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8725    0.6652    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8029   -2.3281    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4590   -1.8232   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.5805    1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9047    0.9036    1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660    1.5961   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531   -0.0441    1.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3260    2.3550    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    2.1376    0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292    1.2426   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859   -0.4896   -1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864    0.4645    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -1.1151    0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734    0.7758    1.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -0.9223   -1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3284   -1.8362   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553   -0.3108   -1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7084    0.7610    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9095   -0.7528    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6261   -0.8177    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 19  1  0
 19  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
 14 16  1  0
 10 12  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 17 36  1  0
 17 37  1  0
 16 35  1  6
 14 34  1  1
 13 32  1  0
 13 33  1  0
 12 31  1  6
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  6
  6 25  1  1
  7 26  1  0
  5 23  1  0
  5 24  1  0
  4 22  1  0
  3 21  1  0
  1 20  1  0
M  END


  Mrv1652309082204302D          

 19 20  0  0  1  0            999 V2000
    4.7597    8.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241    7.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0886    7.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2681    7.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9325    6.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1120    6.2911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6271    6.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765    5.5374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1890    4.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6370    4.2099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8085    3.4029    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8833    4.5454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1688    4.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688    3.3079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5813    2.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    2.5935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9582    2.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582    1.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    5.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1O[C@@H]1C[C@@H]1O[C@H](C[C@@H]1Br)[C@H](O)C\C=C\C#C

> <INCHI_IDENTIFIER>
InChI=1S/C15H21BrO3/c1-3-5-6-7-11(17)14-8-10(16)13(19-14)9-15-12(4-2)18-15/h1,5-6,10-15,17H,4,7-9H2,2H3/b6-5+/t10-,11+,12+,13-,14+,15+/m0/s1

> <INCHI_KEY>
CDQFURANXHAJLL-SMUGRMHISA-N

> <FORMULA>
C15H21BrO3

> <MOLECULAR_WEIGHT>
329.234

> <EXACT_MASS>
328.067408

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.670619908953626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3E)-1-[(2R,4S,5S)-4-bromo-5-{[(2R,3R)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol

> <JCHEM_LOGP>
2.296219306666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.13760872691461

> <JCHEM_PKA_STRONGEST_BASIC>
-3.176009942847549

> <JCHEM_POLAR_SURFACE_AREA>
41.989999999999995

> <JCHEM_REFRACTIVITY>
78.4155

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3E)-1-[(2R,4S,5S)-4-bromo-5-{[(2R,3R)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.885  16.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.258  14.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.632  13.472   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.100  13.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.474  11.904   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.942  11.743   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.037  12.989   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.316  10.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.086   9.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.056   7.858   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       3.376   6.352   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       1.649   8.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.315   7.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.315   6.175   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.085   4.841   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.455   4.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.789   4.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.789   2.531   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.810  10.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁BrO₃

Average Mass

329.2340 Da

Monoisotopic Mass

328.06741 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H]1O[C@@H]1C[C@@H]1O[C@H](C[C@@H]1Br)[C@H](O)C\C=C\C#C

InChI Identifier

InChI=1S/C15H21BrO3/c1-3-5-6-7-11(17)14-8-10(16)13(19-14)9-15-12(4-2)18-15/h1,5-6,10-15,17H,4,7-9H2,2H3/b6-5+/t10-,11+,12+,13-,14+,15+/m0/s1

InChI Key

CDQFURANXHAJLL-SMUGRMHISA-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
Laurencia nipponica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Acetylide
Oxacycle
Organobromide
Organohalogen compound
Alkyl bromide
Organooxygen compound
Organic oxygen compound
Alkyl halide
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

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

29216637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14411918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol (NP0260361)

MOL for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

3D MOL for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

3D SDF for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

3D-SDF for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

PDB for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

3D PDB for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

SMILES for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

INCHI for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

Structure for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)

3D Structure for NP0260361 ((1r,3e)-1-[(2r,4s,5s)-4-bromo-5-{[(2r,3r)-3-ethyloxiran-2-yl]methyl}oxolan-2-yl]hex-3-en-5-yn-1-ol)