NP-MRD: Showing NP-Card for 2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol (NP0249912)

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Record Information

Version

2.0

Created at

2022-09-07 12:36:16 UTC

Updated at

2022-09-07 12:36:16 UTC

NP-MRD ID

NP0249912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol

Description

2-{[(4AS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-4,6-dibromophenol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol is found in Callophycus serratus. Based on a literature review very few articles have been published on 2-{[(4aS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-4,6-dibromophenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214362D          

 32 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072214362D          

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M  END
> <DATABASE_ID>
NP0249912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(Cl)C(Br)CC[C@@]1(C)[C@H](Br)CC[C@@]2(C)C(CC3=CC(Br)=CC(Br)=C3O)C(=C)CC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C26H35Br4ClO/c1-15-6-7-20-25(4,18(15)13-16-12-17(27)14-19(28)23(16)32)10-9-22(30)26(20,5)11-8-21(29)24(2,3)31/h12,14,18,20-22,32H,1,6-11,13H2,2-5H3/t18?,20-,21?,22+,25-,26+/m0/s1

> <INCHI_KEY>
RWUQIKIJRXVZFL-UFRYTPROSA-N

> <FORMULA>
C26H35Br4ClO

> <MOLECULAR_WEIGHT>
718.63

> <EXACT_MASS>
713.910995

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
60.979710002813434

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(4aS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-4,6-dibromophenol

> <JCHEM_LOGP>
10.315910385333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.976812374372993

> <JCHEM_PKA_STRONGEST_BASIC>
-6.982516123073366

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
151.1847

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(4aS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-4,6-dibromophenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       5.335  -3.080   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.405  -4.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.318  -5.853   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       0.498  -7.159   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0      -1.857  -5.907   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.396  -5.961   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.803  -7.446   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      -1.910  -4.368   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   27 Br   UNK     0       5.335   1.540   0.000  0.00  0.00          Br+0
HETATM   28  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0       2.667   6.160   0.000  0.00  0.00          Br+0
HETATM   31  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8   22                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    6    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₅Br₄ClO

Average Mass

718.6300 Da

Monoisotopic Mass

713.91100 Da

IUPAC Name

2-{[(4aS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-4,6-dibromophenol

Traditional Name

2-{[(4aS,5R,6R,8aS)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-4,6-dibromophenol

CAS Registry Number

Not Available

SMILES

CC(C)(Cl)C(Br)CC[C@@]1(C)[C@H](Br)CC[C@@]2(C)C(CC3=CC(Br)=CC(Br)=C3O)C(=C)CC[C@H]12

InChI Identifier

InChI=1S/C26H35Br4ClO/c1-15-6-7-20-25(4,18(15)13-16-12-17(27)14-19(28)23(16)32)10-9-22(30)26(20,5)11-8-21(29)24(2,3)31/h12,14,18,20-22,32H,1,6-11,13H2,2-5H3/t18?,20-,21?,22+,25-,26+/m0/s1

InChI Key

RWUQIKIJRXVZFL-UFRYTPROSA-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
Callophycus serratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
4-bromophenol
2-bromophenol
2-halophenol
4-halophenol
Phenol
Halobenzene
Bromobenzene
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl bromide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	10.32	ChemAxon
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.18 m³·mol⁻¹	ChemAxon
Polarizability	60.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

23076461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163038069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol (NP0249912)

MOL for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

3D MOL for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

3D SDF for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

3D-SDF for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

PDB for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

3D PDB for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

SMILES for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

INCHI for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

Structure for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)

3D Structure for NP0249912 (2-{[(4as,5r,6r,8as)-6-bromo-5-(3-bromo-4-chloro-4-methylpentyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,6-dibromophenol)