NP-MRD: Showing NP-Card for 3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate (NP0161833)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 20:06:11 UTC

Updated at

2022-09-02 20:06:11 UTC

NP-MRD ID

NP0161833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate

Description

3-Chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. 3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate is found in Ptilonia magellanica. 3-Chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    4.4232    1.0489   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    0.7010    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2813    0.2110   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549   -0.1761   -0.9178 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0085    0.9634   -0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    0.3389    0.2556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2671    1.2015    0.4249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7972    1.5589    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    2.4884    1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624    1.0642    2.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900   -0.9623   -0.4474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8998   -1.6826    0.5358 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339   -1.9213   -0.4228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1518   -2.3807   -1.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -3.1320    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2241   -4.0507   -0.2865 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8446   -4.2959    0.3029 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -1.2269   -0.0195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    1.9865   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0955    1.1402    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046    0.1890   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    1.6037    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756   -0.1226    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796    1.0134   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123   -0.6634   -1.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4220   -0.4453   -1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490    1.5594    0.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616    1.6476   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655    0.0126    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    2.4841    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6839    2.2031    2.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    3.5458    1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342   -0.7948   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9307   -2.2290   -2.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883   -2.8782    1.4869 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 18  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  6
  5 27  1  0
  5 28  1  0
  6 29  1  1
  9 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  6
 14 34  1  0
 15 35  1  0
M  END


  Mrv1533004171505012D          

 18 18  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 Br  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  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161833

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1CC(OC(C)=O)C(Cl)C(O)(O1)C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C11H17Br2ClO4/c1-3-4-7-5-8(17-6(2)15)9(14)11(16,18-7)10(12)13/h7-10,16H,3-5H2,1-2H3

> <INCHI_KEY>
MSHMBKPBCVOIHB-UHFFFAOYSA-N

> <FORMULA>
C11H17Br2ClO4

> <MOLECULAR_WEIGHT>
408.51

> <EXACT_MASS>
405.918213

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
31.993877985327053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
2.787380351999999

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.84572996047728

> <JCHEM_PKA_STRONGEST_BASIC>
-4.378284219771229

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
74.74830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       3.840   3.222   0.000  0.00  0.00          Br+0
HETATM   18 Br   UNK     0       1.797   4.937   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13    4                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
3-Chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetic acid	Generator

Chemical Formula

C₁₁H₁₇Br₂ClO₄

Average Mass

408.5100 Da

Monoisotopic Mass

405.91821 Da

IUPAC Name

3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate

Traditional Name

3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CCCC1CC(OC(C)=O)C(Cl)C(O)(O1)C(Br)Br

InChI Identifier

InChI=1S/C11H17Br2ClO4/c1-3-4-7-5-8(17-6(2)15)9(14)11(16,18-7)10(12)13/h7-10,16H,3-5H2,1-2H3

InChI Key

MSHMBKPBCVOIHB-UHFFFAOYSA-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
Ptilonia magellanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Bromohydrin
Carboxylic acid ester
Chlorohydrin
Halohydrin
Hemiacetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alkyl bromide
Organohalogen compound
Organobromide
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alkyl halide
Alkyl chloride
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	3.93	ALOGPS
logP	2.79	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	-4.4	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	74.75 m³·mol⁻¹	ChemAxon
Polarizability	31.99 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

73837979

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate (NP0161833)

MOL for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

3D MOL for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

3D SDF for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

3D-SDF for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

PDB for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

3D PDB for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

SMILES for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

INCHI for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

Structure for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)

3D Structure for NP0161833 (3-chloro-2-(dibromomethyl)-2-hydroxy-6-propyloxan-4-yl acetate)