NP-MRD: Showing NP-Card for (3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran (NP0145977)

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Record Information

Version

2.0

Created at

2022-09-02 01:17:10 UTC

Updated at

2022-09-02 01:17:10 UTC

NP-MRD ID

NP0145977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran

Description

(3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-2,3,5,6,7,7a-hexahydro-1-benzofuran belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review very few articles have been published on (3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-2,3,5,6,7,7a-hexahydro-1-benzofuran.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203172D          

 13 14  0  0  1  0            999 V2000
    2.3522    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825    1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0145977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C=C2[C@H](Cl)CO[C@H]2C[C@H]1Br

> <INCHI_IDENTIFIER>
InChI=1S/C10H14BrClO/c1-10(2)4-6-7(12)5-13-8(6)3-9(10)11/h4,7-9H,3,5H2,1-2H3/t7-,8+,9-/m1/s1

> <INCHI_KEY>
IZRFVDARYRVGND-HRDYMLBCSA-N

> <FORMULA>
C10H14BrClO

> <MOLECULAR_WEIGHT>
265.58

> <EXACT_MASS>
263.991656

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.48779670983754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-2,3,5,6,7,7a-hexahydro-1-benzofuran

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
2.7467781296666667

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.187072686033326

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
58.328300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2H-1-benzofuran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.391   0.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.381   2.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -0.744   0.132   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       5.198   4.383   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄BrClO

Average Mass

265.5800 Da

Monoisotopic Mass

263.99166 Da

IUPAC Name

(3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-2,3,5,6,7,7a-hexahydro-1-benzofuran

Traditional Name

(3S,6R,7aS)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2H-1-benzofuran

CAS Registry Number

Not Available

SMILES

CC1(C)C=C2[C@H](Cl)CO[C@H]2C[C@H]1Br

InChI Identifier

InChI=1S/C10H14BrClO/c1-10(2)4-6-7(12)5-13-8(6)3-9(10)11/h4,7-9H,3,5H2,1-2H3/t7-,8+,9-/m1/s1

InChI Key

IZRFVDARYRVGND-HRDYMLBCSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
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	3.67	ALOGPS
logP	2.75	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	58.33 m³·mol⁻¹	ChemAxon
Polarizability	23.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

10472364

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163017184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran (NP0145977)

MOL for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

3D MOL for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

3D SDF for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

3D-SDF for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

PDB for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

3D PDB for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

SMILES for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

INCHI for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

Structure for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)

3D Structure for NP0145977 ((3s,6r,7as)-6-bromo-3-chloro-5,5-dimethyl-3,6,7,7a-tetrahydro-2h-1-benzofuran)