NP-MRD: Showing NP-Card for 12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one (NP0187529)

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Record Information

Version

2.0

Created at

2022-09-04 03:43:11 UTC

Updated at

2022-09-04 03:43:12 UTC

NP-MRD ID

NP0187529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one

Description

12-{3-Bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one is found in Aplysia kurodai. 12-{3-Bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503012D          

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M  END

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  Mrv1533004201503012D          

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M  END
> <DATABASE_ID>
NP0187529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(CC=C(C)CCCC(C)C(=O)C=CC(C)(C)O)C(CCN(C)C)=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C26H40BrNO4/c1-18(9-8-10-19(2)22(29)13-15-26(3,4)31)11-12-20-17-23(30)25(32-7)24(27)21(20)14-16-28(5)6/h11,13,15,17,19,30-31H,8-10,12,14,16H2,1-7H3

> <INCHI_KEY>
KVYNONOLWFDHIW-UHFFFAOYSA-N

> <FORMULA>
C26H40BrNO4

> <MOLECULAR_WEIGHT>
510.513

> <EXACT_MASS>
509.214072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.49344626347536

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
5.73896413871274

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.98600261938142

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.72300416056479

> <JCHEM_PKA_STRONGEST_BASIC>
8.829367544564912

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
139.01329999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -5.335  16.940   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  14.630   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.772   6.366   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.232   9.034   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -9.336  11.550   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -9.336  10.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669  12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0      -6.668  14.630   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    7   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25    3   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀BrNO₄

Average Mass

510.5130 Da

Monoisotopic Mass

509.21407 Da

IUPAC Name

12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one

Traditional Name

12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(CC=C(C)CCCC(C)C(=O)C=CC(C)(C)O)C(CCN(C)C)=C1Br

InChI Identifier

InChI=1S/C26H40BrNO4/c1-18(9-8-10-19(2)22(29)13-15-26(3,4)31)11-12-20-17-23(30)25(32-7)24(27)21(20)14-16-28(5)6/h11,13,15,17,19,30-31H,8-10,12,14,16H2,1-7H3

InChI Key

KVYNONOLWFDHIW-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
Aplysia kurodai	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Methoxyphenol
Phenethylamine
Phenoxy compound
Anisole
3-halophenol
3-bromophenol
Methoxybenzene
Phenol ether
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Bromobenzene
Phenol
Aryl bromide
Aryl halide
Benzenoid
Monocyclic benzene moiety
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Tertiary alcohol
Ketone
Tertiary aliphatic amine
Tertiary amine
Ether
Organic nitrogen compound
Organohalogen compound
Organobromide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
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	5.39	ALOGPS
logP	5.74	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	139.01 m³·mol⁻¹	ChemAxon
Polarizability	53.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

85089981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one (NP0187529)

MOL for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

3D MOL for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

3D SDF for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

3D-SDF for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

PDB for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

3D PDB for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

SMILES for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

INCHI for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

Structure for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)

3D Structure for NP0187529 (12-{3-bromo-2-[2-(dimethylamino)ethyl]-5-hydroxy-4-methoxyphenyl}-2-hydroxy-2,6,10-trimethyldodeca-3,10-dien-5-one)