NP-MRD: Showing NP-Card for (+)-9-Acetylisoobtusol (NP0080995)

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Record Information

Version

2.0

Created at

2022-04-29 01:59:06 UTC

Updated at

2022-04-29 01:59:06 UTC

NP-MRD ID

NP0080995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-9-Acetylisoobtusol

Description

9-Acetyllisoobtusol belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. (+)-9-Acetylisoobtusol is found in Aplysia dactylomela. Based on a literature review very few articles have been published on 9-acetyllisoobtusol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 48  0  0  0  0  0  0  0  0999 V2000
   -0.4684   -1.9641   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0605   -0.8268   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1086   -0.8541    0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -0.0568    0.1472 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3158   -0.0947    1.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5130   -0.6795    0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561   -0.6891    1.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6783   -1.2399   -0.3688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7463    1.3551   -0.0617 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9220    2.2784    1.6331 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4201    1.5326   -0.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5397    1.7048   -2.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202    2.8614   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    0.4826   -0.3501 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6750    0.4140   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0828    0.5604   -0.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648   -0.1614    0.2852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8007   -1.6058    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1576    0.6737    0.8532 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4385   -0.0058    1.3530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8205   -1.5240    2.0174 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.9453    0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0625   -2.9013   -0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814   -2.1205   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8912   -0.3115    1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -1.8784    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -0.5753   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3885   -0.3827    2.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4733   -0.0290    1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992   -1.7250    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5096    1.8365   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244    2.5781   -2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083    1.9497   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3444    0.7669   -2.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135    2.9006    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0467    3.1671   -0.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514    3.6244   -0.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370    1.2871   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087   -0.4550   -2.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7427    0.1473   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3786    1.6466   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218   -1.8855    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0983   -2.2589    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7964   -1.8562   -1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517    0.5485    2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869    1.9243    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6472    1.0449    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 14  2  1  0
 14 15  1  6
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 17 20  1  0
 20 21  1  0
 20 22  1  0
 14 11  1  0
 11 12  1  6
 11 13  1  0
 11  9  1  0
  9 10  1  0
  9  4  1  0
 22 14  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  4 27  1  6
  3 25  1  0
  3 26  1  0
  1 23  1  0
  1 24  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  1
 22 46  1  0
 22 47  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
  9 31  1  6
M  END


  Mrv1652304292203592D          

 22 23  0  0  1  0            999 V2000
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8266   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    0.7998    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9179    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 Br  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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 13 15  1  1  0  0  0
 12 16  1  6  0  0  0
 12 17  1  1  0  0  0
  2 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  1 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0080995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC(=C)[C@]2(CC[C@](C)(Br)[C@@H](Cl)C2)C(C)(C)[C@H]1Br

> <INCHI_IDENTIFIER>
InChI=1S/C17H25Br2ClO2/c1-10-8-12(22-11(2)21)14(18)15(3,4)17(10)7-6-16(5,19)13(20)9-17/h12-14H,1,6-9H2,2-5H3/t12-,13-,14-,16-,17+/m0/s1

> <INCHI_KEY>
LCTBUAFKAFMZQT-CUINURIISA-N

> <FORMULA>
C17H25Br2ClO2

> <MOLECULAR_WEIGHT>
456.64

> <EXACT_MASS>
453.990984

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38439845942117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-yl acetate

> <ALOGPS_LOGP>
5.96

> <JCHEM_LOGP>
5.040029164333332

> <ALOGPS_LOGS>
-6.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0057618137393645

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
96.798

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.410  -1.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.157  -2.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       5.954  -1.897   0.000  0.00  0.00          Cl+0
HETATM   16 Br   UNK     0       7.313   1.493   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       7.313   0.047   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.056   2.104   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   22 Br   UNK     0      -0.206  -1.897   0.000  0.00  0.00          Br+0
CONECT    1    2    7   22                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10   14                                             
CONECT    7    6    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   17                                             
CONECT   13   12   14   15                                                  
CONECT   14   13    6                                                       
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    2   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₅Br₂ClO₂

Average Mass

456.6400 Da

Monoisotopic Mass

453.99098 Da

IUPAC Name

(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-yl acetate

Traditional Name

(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC(=C)[C@]2(CC[C@](C)(Br)[C@@H](Cl)C2)C(C)(C)[C@H]1Br

InChI Identifier

InChI=1S/C17H25Br2ClO2/c1-10-8-12(22-11(2)21)14(18)15(3,4)17(10)7-6-16(5,19)13(20)9-17/h12-14H,1,6-9H2,2-5H3/t12-,13-,14-,16-,17+/m0/s1

InChI Key

LCTBUAFKAFMZQT-CUINURIISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane sesquiterpenoid
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alkyl bromide
Organochloride
Organobromide
Organohalogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5.96	ALOGPS
logP	5.04	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Basic)	-7	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	2	ChemAxon
Refractivity	96.8 m³·mol⁻¹	ChemAxon
Polarizability	39.38 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

10242602

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21606563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-9-Acetylisoobtusol (NP0080995)

MOL for NP0080995 ((+)-9-Acetylisoobtusol)

3D MOL for NP0080995 ((+)-9-Acetylisoobtusol)

3D SDF for NP0080995 ((+)-9-Acetylisoobtusol)

3D-SDF for NP0080995 ((+)-9-Acetylisoobtusol)

PDB for NP0080995 ((+)-9-Acetylisoobtusol)

3D PDB for NP0080995 ((+)-9-Acetylisoobtusol)

SMILES for NP0080995 ((+)-9-Acetylisoobtusol)

INCHI for NP0080995 ((+)-9-Acetylisoobtusol)

Structure for NP0080995 ((+)-9-Acetylisoobtusol)

3D Structure for NP0080995 ((+)-9-Acetylisoobtusol)