NP-MRD: Showing NP-Card for 3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid (NP0292598)

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Record Information

Version

2.0

Created at

2022-09-10 00:12:17 UTC

Updated at

2022-09-10 00:12:18 UTC

NP-MRD ID

NP0292598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid

Description

3-Bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid is found in Callophycus serratus. 3-Bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511042D          

 32 34  0  0  0  0            999 V2000
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   -0.1620   -3.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   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
    0.0000   -1.6500    0.0000 Br  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
    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 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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251511042D          

 32 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0292598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC1(C)C(Br)CCC2(C)C(CC3=CC(=CC(Br)=C3O)C(O)=O)C(=C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C27H36Br2O3/c1-16(2)7-6-11-27(5)22-9-8-17(3)20(26(22,4)12-10-23(27)29)14-18-13-19(25(31)32)15-21(28)24(18)30/h7,13,15,20,22-23,30H,3,6,8-12,14H2,1-2,4-5H3,(H,31,32)

> <INCHI_KEY>
JGBUIUFDBKKZNT-UHFFFAOYSA-N

> <FORMULA>
C27H36Br2O3

> <MOLECULAR_WEIGHT>
568.39

> <EXACT_MASS>
566.103121

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.70231721087902

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
7.12

> <JCHEM_LOGP>
8.450500504

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.567164755696936

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.242050529163502

> <JCHEM_PKA_STRONGEST_BASIC>
-6.781124958660375

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
139.385

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.292  -7.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.302  -6.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.214  -6.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.204  -5.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0       0.000  -3.080   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0       8.002   6.160   0.000  0.00  0.00          Br+0
HETATM   22  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.829  -5.172   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    6   12                                                  
CONECT   32    2                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-Bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoate	Generator

Chemical Formula

C₂₇H₃₆Br₂O₃

Average Mass

568.3900 Da

Monoisotopic Mass

566.10312 Da

IUPAC Name

3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoic acid

Traditional Name

3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC1(C)C(Br)CCC2(C)C(CC3=CC(=CC(Br)=C3O)C(O)=O)C(=C)CCC12

InChI Identifier

InChI=1S/C27H36Br2O3/c1-16(2)7-6-11-27(5)22-9-8-17(3)20(26(22,4)12-10-23(27)29)14-18-13-19(25(31)32)15-21(28)24(18)30/h7,13,15,20,22-23,30H,3,6,8-12,14H2,1-2,4-5H3,(H,31,32)

InChI Key

JGBUIUFDBKKZNT-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
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
Hydroxybenzoic acid
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Halobenzoic acid
3-halobenzoic acid
Benzoic acid or derivatives
Benzoic acid
2-bromophenol
2-halophenol
Benzoyl
Phenol
Halobenzene
Bromobenzene
Benzenoid
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alkyl halide
Alkyl bromide
Organic oxide
Organohalogen compound
Organobromide
Organooxygen compound
Hydrocarbon derivative
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	7.12	ALOGPS
logP	8.45	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.38 m³·mol⁻¹	ChemAxon
Polarizability	55.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

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

74065851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid (NP0292598)

MOL for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

3D MOL for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

3D SDF for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

3D-SDF for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

PDB for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

3D PDB for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

SMILES for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

INCHI for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

Structure for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)

3D Structure for NP0292598 (3-bromo-5-{[6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid)