NP-MRD: Showing NP-Card for 3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde (NP0327338)

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Record Information

Version

2.0

Created at

2022-09-12 09:49:53 UTC

Updated at

2022-09-12 09:49:53 UTC

NP-MRD ID

NP0327338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

Description

3-Bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde is found in Neonectria coccinea. Based on a literature review very few articles have been published on 3-bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122211492D          

 28 29  0  0  1  0            999 V2000
    5.2612   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5434   -2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131   -2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -3.1567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1401   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.5692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0993   -3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -4.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -4.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -4.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -4.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -3.5692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2414   -3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559   -2.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8862   -1.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289   -1.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9468   -0.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0414   -1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5717   -0.5698    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.3236   -1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1360   -2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7933   -2.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0754   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5451   -4.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9808   -2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4505   -3.0978    0.0000 O   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  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1652309122211492D          

 28 29  0  0  1  0            999 V2000
    5.2612   -1.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5434   -2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131   -2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -3.1567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1401   -2.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.5692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0993   -3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -4.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -4.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -4.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -4.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -3.5692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2414   -3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559   -2.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8862   -1.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986   -1.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2289   -1.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9468   -0.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0414   -1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5717   -0.5698    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.3236   -1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1360   -2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7933   -2.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0754   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5451   -4.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9808   -2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4505   -3.0978    0.0000 O   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  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC(=O)[C@@H](C)[C@]1(C)\C=C\C(\C)=C\CC1=C(O)C(Br)=C(C)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29BrO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m0/s1

> <INCHI_KEY>
FYCZENHNNCGSHQ-OLWBNLDESA-N

> <FORMULA>
C23H29BrO4

> <MOLECULAR_WEIGHT>
449.385

> <EXACT_MASS>
448.124922

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.310477106767685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

> <JCHEM_LOGP>
6.818976827666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.704802642663768

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.058558437674201

> <JCHEM_PKA_STRONGEST_BASIC>
-6.05668981410856

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
119.21919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.821  -2.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.348  -3.801   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.358  -4.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.841  -4.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.851  -5.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.861  -4.713   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.185  -6.663   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.519  -5.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.185  -8.203   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.851  -8.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.518  -8.203   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.184  -8.973   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.518  -6.663   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.184  -5.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.864  -4.068   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.854  -2.888   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.371  -3.156   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.361  -1.976   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.834  -0.529   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.877  -2.243   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      17.867  -1.064   0.000  0.00  0.00          Br+0
HETATM   22  C   UNK     0      17.404  -3.691   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.921  -3.958   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.414  -4.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.941  -6.317   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.951  -7.497   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.898  -4.603   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.908  -5.783   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   17   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₉BrO₄

Average Mass

449.3850 Da

Monoisotopic Mass

448.12492 Da

IUPAC Name

3-bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

Traditional Name

3-bromo-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1S,2S,6S)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC(=O)[C@@H](C)[C@]1(C)\C=C\C(\C)=C\CC1=C(O)C(Br)=C(C)C(C=O)=C1O

InChI Identifier

InChI=1S/C23H29BrO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+/t14-,16+,23+/m0/s1

InChI Key

FYCZENHNNCGSHQ-OLWBNLDESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neonectria coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
4-halophenol
2-halophenol
M-cresol
2-bromophenol
Benzoyl
4-bromophenol
Resorcinol
Halobenzene
Bromobenzene
Toluene
Phenol
Benzenoid
Aryl halide
Monocyclic benzene moiety
Aryl bromide
Vinylogous acid
Cyclic ketone
Ketone
Organobromide
Hydrocarbon derivative
Organohalogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.82	ChemAxon
pKa (Strongest Acidic)	6.06	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.22 m³·mol⁻¹	ChemAxon
Polarizability	45.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163185240

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-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde (NP0327338)

MOL for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

3D MOL for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

3D SDF for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

3D-SDF for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

PDB for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

3D PDB for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

SMILES for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

INCHI for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

Structure for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)

3D Structure for NP0327338 (3-bromo-4,6-dihydroxy-2-methyl-5-[(2e,4e)-3-methyl-5-[(1s,2s,6s)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dien-1-yl]benzaldehyde)