NP-MRD: Showing NP-Card for 4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate (NP0310924)

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Record Information

Version

2.0

Created at

2022-09-11 06:34:24 UTC

Updated at

2022-09-11 06:34:24 UTC

NP-MRD ID

NP0310924

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate

Description

Allolaurinterol acetate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. 4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate is found in Aplysia dactylomela. 4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate was first documented in 2012 (PMID: 22233863). Based on a literature review very few articles have been published on Allolaurinterol acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.1769   -0.0204    0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0665    0.1136    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    0.0596   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4236   -0.2306   -1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440   -0.5716   -0.1176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7182   -1.9294    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4395   -0.9013    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8793   -2.1208    0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2145   -2.4321    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7460   -4.0897    1.5121 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -1.5360    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350   -1.8266    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8062   -0.3305   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4403   -0.0422   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1221    1.1791   -0.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    2.3644   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    3.7104   -0.8804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911    2.2734    0.6480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6581    0.3579    0.7539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4641    1.8205    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1052   -0.1899    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    0.0356    2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863    1.0628   -1.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5309   -0.7076   -1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881    0.6667   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -1.0913   -2.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045   -2.6926   -0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -1.8060   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7008   -2.2056    1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1486   -2.8605    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -0.9655    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7930   -2.7516    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1596   -1.8556   -0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205    0.4150   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    4.4421   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    3.7766   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822    4.0324   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6218    0.1212    1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783    2.1750   -0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285    2.3032    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    2.2479    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  0
 14  7  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 19 38  1  1
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
M  END


  Mrv1652309112208342D          

 20 21  0  0  1  0            999 V2000
   -0.6525   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449   -1.0572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7969   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662   -0.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -0.1741    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4112    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632    1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6042    0.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    0.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7548    0.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0097    1.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577    1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167    1.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226   -1.5422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2072   -1.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  5 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0310924

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=C)CC[C@@]1(C)C1=CC(Br)=C(C)C=C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H21BrO2/c1-10-6-7-17(5,12(10)3)14-9-15(18)11(2)8-16(14)20-13(4)19/h8-9,12H,1,6-7H2,2-5H3/t12-,17+/m0/s1

> <INCHI_KEY>
LVYHDYGLTMWWKI-YVEFUNNKSA-N

> <FORMULA>
C17H21BrO2

> <MOLECULAR_WEIGHT>
337.257

> <EXACT_MASS>
336.072493

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.04760074088736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-bromo-2-[(1R,2S)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate

> <JCHEM_LOGP>
5.059540884666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.142206182531744

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
84.79479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-2-[(1R,2S)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.218  -5.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.313  -4.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.227  -4.343   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.703  -2.879   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.457  -1.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.488  -0.829   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.573  -0.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.080  -1.149   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.110  -0.005   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0      -4.617  -0.325   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0      -2.634   1.460   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.665   2.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.128   1.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.097   0.636   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.409   0.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.885   2.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.854   3.565   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.391   2.741   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.789  -2.879   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.253  -2.403   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   19                                             
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Allolaurinterol acetic acid	Generator

Chemical Formula

C₁₇H₂₁BrO₂

Average Mass

337.2570 Da

Monoisotopic Mass

336.07249 Da

IUPAC Name

4-bromo-2-[(1R,2S)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate

Traditional Name

4-bromo-2-[(1R,2S)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=C)CC[C@@]1(C)C1=CC(Br)=C(C)C=C1OC(C)=O

InChI Identifier

InChI=1S/C17H21BrO2/c1-10-6-7-17(5,12(10)3)14-9-15(18)11(2)8-16(14)20-13(4)19/h8-9,12H,1,6-7H2,2-5H3/t12-,17+/m0/s1

InChI Key

LVYHDYGLTMWWKI-YVEFUNNKSA-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 dactylomela	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Bromobenzene
Halobenzene
Toluene
Aryl bromide
Monocyclic benzene moiety
Aryl halide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organobromide
Organohalogen compound
Carbonyl group
Hydrocarbon derivative
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	5.06	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.79 m³·mol⁻¹	ChemAxon
Polarizability	33.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

10199041

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14239678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li XD, Miao FP, Li K, Ji NY: Sesquiterpenes and acetogenins from the marine red alga Laurencia okamurai. Fitoterapia. 2012 Apr;83(3):518-22. doi: 10.1016/j.fitote.2011.12.018. Epub 2011 Dec 30. [PubMed:22233863 ]
LOTUS database [Link]

Showing NP-Card for 4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate (NP0310924)

MOL for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

3D MOL for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

3D SDF for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

3D-SDF for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

PDB for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

3D PDB for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

SMILES for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

INCHI for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

Structure for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)

3D Structure for NP0310924 (4-bromo-2-[(1r,2s)-1,2-dimethyl-3-methylidenecyclopentyl]-5-methylphenyl acetate)