NP-MRD: Showing NP-Card for Prepacifenol epoxide (NP0064622)

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Record Information

Version

2.0

Created at

2022-04-28 08:48:59 UTC

Updated at

2022-04-28 08:48:59 UTC

NP-MRD ID

NP0064622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prepacifenol epoxide

Description

Prepacifenol epoxide 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. Prepacifenol epoxide is found in Aplysia californica, Aplysia dactylomela, Laurencia johnstonii and Laurencia spp.. Based on a literature review very few articles have been published on Prepacifenol epoxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.5678   -2.1746    0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808   -0.8877    0.1984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7940   -1.0963   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2833   -0.6336    1.1982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3751   -1.7397    2.7935 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369   -0.5516    0.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610    0.5307    1.1320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3917    1.5821    0.2265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4219    2.3550    0.8841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1032    1.4883   -0.2833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7685    2.3575   -1.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397    0.2881    0.0612 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7483   -0.0194   -1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    0.4318   -0.7780 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2511   -0.3713   -2.1814 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7232   -0.0009    0.5235 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4756   -1.3329    0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.1898    1.0245 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7134   -0.1684    1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4808    0.6011    1.3300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4024    0.5632    2.4349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -2.2888    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856   -2.4415    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859   -2.9871    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -1.8007   -1.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2078   -0.1443   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -1.5750   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.9878    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956    2.1213   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2708    2.4642   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2724    1.8991   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2026    3.3765   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054   -1.0960   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    0.4597   -2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075    1.5208   -0.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2123   -1.2872   -0.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0761   -1.4224    1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -2.1607    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -1.2332    1.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524    0.2738    2.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7809    1.6904    1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1307    1.2324    3.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  1
  4  2  1  0
  2  1  1  1
  2  3  1  0
 12  2  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  1
 16 19  1  0
 19 20  1  0
 20 21  1  0
  8 10  1  0
  4  7  1  0
 20 12  1  0
 12 10  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
  8 29  1  6
  7 28  1  1
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 17 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  6
 21 42  1  0
M  END


  Mrv1652304282210492D          

 21 24  0  0  1  0            999 V2000
    4.3038    1.5493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5738    0.7698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0337    0.1461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2236    0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9535    1.0816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4936    1.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    2.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    2.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135    0.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033    0.6139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3333    1.3934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8734    2.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.8611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7539    2.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5448    1.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6912    1.9114    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0632   -0.0098    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4440    0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936   -0.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    1.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    2.3595    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  6  0  0  0
  9 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
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 11 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
  4 18  1  6  0  0  0
  4 19  1  0  0  0  0
  3 19  1  1  0  0  0
  2 20  1  6  0  0  0
  1 20  1  0  0  0  0
  1 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12O[C@@H]1[C@H]1O[C@@]1(Br)C(C)(C)[C@@]21C[C@H](Br)[C@@](C)(Cl)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21Br2ClO3/c1-11(2)14(5-7(16)12(3,18)6-8(14)19)13(4)9(20-13)10-15(11,17)21-10/h7-10,19H,5-6H2,1-4H3/t7-,8-,9+,10+,12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
AHEAISCIGHPMGI-WJZNTHCVSA-N

> <FORMULA>
C15H21Br2ClO3

> <MOLECULAR_WEIGHT>
444.59

> <EXACT_MASS>
441.954598

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.165888813662164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,1'R,2S,2'R,4S,4'S,5S,7'R)-5,7'-dibromo-4-chloro-4,4',6',6'-tetramethyl-3',8'-dioxaspiro[cyclohexane-1,5'-tricyclo[5.1.0.0^{2,4}]octane]-2-ol

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.149908683333333

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.526580807350673

> <JCHEM_PKA_STRONGEST_BASIC>
-3.005873554864815

> <JCHEM_POLAR_SURFACE_AREA>
41.989999999999995

> <JCHEM_REFRACTIVITY>
86.7663

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'R,2S,2'R,4S,4'S,5S,7'R)-5,7'-dibromo-4-chloro-4,4',6',6'-tetramethyl-3',8'-dioxaspiro[cyclohexane-1,5'-tricyclo[5.1.0.0^{2,4}]octane]-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.034   2.892   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.538   1.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.530   0.273   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.017   0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.513   2.019   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.521   3.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.393   4.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.760   4.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.505   0.855   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.993   1.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.489   2.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.497   3.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.009   3.474   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.141   5.009   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.017   2.148   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       1.290   3.568   0.000  0.00  0.00          Cl+0
HETATM   17 Br   UNK     0       1.985  -0.018   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       4.562   0.060   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.521  -0.891   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.546   2.601   0.000  0.00  0.00           O+0
HETATM   21 Br   UNK     0       8.325   4.404   0.000  0.00  0.00          Br+0
CONECT    1    2    6   20   21                                             
CONECT    2    1    3   20                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   18   19                                             
CONECT    5    4    6    9   13                                             
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   15   16                                             
CONECT   12   11   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    4                                                            
CONECT   19    4    3                                                       
CONECT   20    2    1                                                       
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁Br₂ClO₃

Average Mass

444.5900 Da

Monoisotopic Mass

441.95460 Da

IUPAC Name

(1R,1'R,2S,2'R,4S,4'S,5S,7'R)-5,7'-dibromo-4-chloro-4,4',6',6'-tetramethyl-3',8'-dioxaspiro[cyclohexane-1,5'-tricyclo[5.1.0.0^{2,4}]octane]-2-ol

Traditional Name

(1R,1'R,2S,2'R,4S,4'S,5S,7'R)-5,7'-dibromo-4-chloro-4,4',6',6'-tetramethyl-3',8'-dioxaspiro[cyclohexane-1,5'-tricyclo[5.1.0.0^{2,4}]octane]-2-ol

CAS Registry Number

Not Available

SMILES

C[C@@]12O[C@@H]1[C@H]1O[C@@]1(Br)C(C)(C)[C@@]21C[C@H](Br)[C@@](C)(Cl)C[C@@H]1O

InChI Identifier

InChI=1S/C15H21Br2ClO3/c1-11(2)14(5-7(16)12(3,18)6-8(14)19)13(4)9(20-13)10-15(11,17)21-10/h7-10,19H,5-6H2,1-4H3/t7-,8-,9+,10+,12-,13+,14-,15+/m0/s1

InChI Key

AHEAISCIGHPMGI-WJZNTHCVSA-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 californica	Animalia	KNApSAcK
Aplysia dactylomela	Animalia	KNApSAcK
Laurencia johnstonii	-	KNApSAcK
Laurencia spp.	-	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
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.96	ALOGPS
logP	3.15	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.77 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00021633

Chemspider ID

20005703

KEGG Compound ID

C17127

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15385747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Prepacifenol epoxide (NP0064622)

MOL for NP0064622 (Prepacifenol epoxide)

3D MOL for NP0064622 (Prepacifenol epoxide)

3D SDF for NP0064622 (Prepacifenol epoxide)

3D-SDF for NP0064622 (Prepacifenol epoxide)

PDB for NP0064622 (Prepacifenol epoxide)

3D PDB for NP0064622 (Prepacifenol epoxide)

SMILES for NP0064622 (Prepacifenol epoxide)

INCHI for NP0064622 (Prepacifenol epoxide)

Structure for NP0064622 (Prepacifenol epoxide)

3D Structure for NP0064622 (Prepacifenol epoxide)