NP-MRD: Showing NP-Card for (2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal (NP0241928)

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Record Information

Version

2.0

Created at

2022-09-07 02:07:16 UTC

Updated at

2022-09-07 02:07:16 UTC

NP-MRD ID

NP0241928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal

Description

Rogiolal belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. (2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal is found in Laurencia dendroidea. Based on a literature review very few articles have been published on Rogiolal.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    2.5530    1.3362    0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.0855    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788   -0.9022   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372   -0.7561   -0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7330   -1.6980   -0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745    0.0199    0.2974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2221    1.2110   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478    0.8955   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274   -0.0525   -0.2037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5982    0.4894    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -0.2474   -0.8480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375   -1.3895   -0.2230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1332   -2.2033   -1.9140 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -1.2836   -0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    1.8103   -0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403    1.1293    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8287    2.0399    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1443   -1.8460   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880    0.1689   -0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1580    0.1149    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401    1.6303   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023    2.0245    0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1051    1.8665   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    0.4280   -2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178    1.3004    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6086    0.9477    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6170   -0.3058    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849   -1.1869   -0.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -2.0765    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -2.0926    0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2906   -1.4578   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  1
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  1
 14 30  1  0
 14 31  1  0
M  END


  Mrv1652309072204072D          

 14 14  0  0  1  0            999 V2000
    1.4289   -1.6500    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  2  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/C=O)[C@H]1CC[C@@](C)(O)[C@@H](Br)C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H17BrO2/c1-8(4-6-13)9-3-5-11(2,14)10(12)7-9/h4,6,9-10,14H,3,5,7H2,1-2H3/b8-4+/t9-,10-,11+/m0/s1

> <INCHI_KEY>
NMCFXEPPDQBROS-SLEYYXBJSA-N

> <FORMULA>
C11H17BrO2

> <MOLECULAR_WEIGHT>
261.159

> <EXACT_MASS>
260.041193

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.329314217046544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal

> <JCHEM_LOGP>
1.9649368133333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.050737733090187

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2140073155463513

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
61.1756

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal

> <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  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₇BrO₂

Average Mass

261.1590 Da

Monoisotopic Mass

260.04119 Da

IUPAC Name

(2E)-3-[(1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal

Traditional Name

(2E)-3-[(1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal

CAS Registry Number

Not Available

SMILES

C\C(=C/C=O)[C@H]1CC[C@@](C)(O)[C@@H](Br)C1

InChI Identifier

InChI=1S/C11H17BrO2/c1-8(4-6-13)9-3-5-11(2,14)10(12)7-9/h4,6,9-10,14H,3,5,7H2,1-2H3/b8-4+/t9-,10-,11+/m0/s1

InChI Key

NMCFXEPPDQBROS-SLEYYXBJSA-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
Laurencia dendroidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
P-menthane monoterpenoid
Cyclohexanol
Cyclohexyl halide
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Tertiary alcohol
Halohydrin
Bromohydrin
Organohalogen compound
Organic oxide
Organic oxygen compound
Aldehyde
Carbonyl group
Alcohol
Alkyl halide
Organobromide
Organooxygen compound
Alkyl bromide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	1.96	ChemAxon
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.18 m³·mol⁻¹	ChemAxon
Polarizability	24.33 Å³	ChemAxon
Number of Rings	1	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

10203522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21587196

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal (NP0241928)

MOL for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

3D MOL for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

3D SDF for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

3D-SDF for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

PDB for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

3D PDB for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

SMILES for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

INCHI for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

Structure for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)

3D Structure for NP0241928 ((2e)-3-[(1s,3s,4r)-3-bromo-4-hydroxy-4-methylcyclohexyl]but-2-enal)