NP-MRD: Showing NP-Card for (1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate (NP0157562)

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Record Information

Version

2.0

Created at

2022-09-02 14:58:29 UTC

Updated at

2022-09-02 14:58:29 UTC

NP-MRD ID

NP0157562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate

Description

8Alpha-acetoxyelemol belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Based on a literature review very few articles have been published on 8alpha-acetoxyelemol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 48  0  0  0  0  0  0  0  0999 V2000
   -2.7563    2.2047   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136    1.6669   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    0.5075   -0.5555 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9802   -0.4431   -1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639    0.9624   -1.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613    0.6678   -0.3683 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3630    1.7181    0.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4161    2.5888    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    3.6898    1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745    2.4550   -0.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283   -0.6917    0.2529 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8419   -1.7131   -0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -3.0561    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2675   -1.3699   -1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -1.8741   -1.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -1.2286    0.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -0.0840    0.7710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3092   -0.4584    1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610    0.1658    2.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2311   -1.5661    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433    3.0478   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.8569   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238    2.0520    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131   -1.4628   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7255   -0.0396   -2.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1092   -0.3880   -1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777    0.6019   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302    2.0919   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    0.7361   -1.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    4.6524    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    3.4391    2.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6895    3.7384    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -0.6235    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -3.5695   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -3.7394   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -2.9050    1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -2.3206   -1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094   -1.0057   -0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -0.6629   -1.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -2.0437   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153   -1.6491    1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4824   -2.0687    0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    0.6914    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0085    0.9827    2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216   -0.0687    3.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -2.1129    2.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1185   -1.0806    0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443   -2.2916    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  1
  2  1  2  3
  3 17  1  0
 17 16  1  0
 16 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  3
 11  6  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  6 29  1  6
  5 27  1  0
  5 28  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  2 23  1  0
  1 21  1  0
  1 22  1  0
 17 43  1  1
 16 41  1  0
 16 42  1  0
 11 33  1  1
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 19 44  1  0
 19 45  1  0
M  END


  Mrv1652309022216582D          

 20 20  0  0  1  0            999 V2000
    0.4663    2.6447    0.0000 C   0  0  0  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
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  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  2  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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157562

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O3/c1-8-17(7)10-15(20-12(4)18)14(16(5,6)19)9-13(17)11(2)3/h8,13-15,19H,1-2,9-10H2,3-7H3/t13-,14-,15-,17+/m1/s1

> <INCHI_KEY>
OVOINWQJBHVFGP-ANQUJSFKSA-N

> <FORMULA>
C17H28O3

> <MOLECULAR_WEIGHT>
280.408

> <EXACT_MASS>
280.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.452227968446294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,5R)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.7874294446666656

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.98504240393983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.805342452516717

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
80.92999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,5R)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.870   4.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   17                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   16                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
8a-Acetoxyelemol	Generator
8Α-acetoxyelemol	Generator

Chemical Formula

C₁₇H₂₈O₃

Average Mass

280.4080 Da

Monoisotopic Mass

280.20384 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@](C)(C=C)[C@H](C[C@H]1C(C)(C)O)C(C)=C

InChI Identifier

InChI=1S/C17H28O3/c1-8-17(7)10-15(20-12(4)18)14(16(5,6)19)9-13(17)11(2)3/h8,13-15,19H,1-2,9-10H2,3-7H3/t13-,14-,15-,17+/m1/s1

InChI Key

OVOINWQJBHVFGP-ANQUJSFKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Elemane sesquiterpenoids

Alternative Parents

Substituents

Elemane sesquiterpenoid
Tertiary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012001

Chemspider ID

23339458

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate (NP0157562)

MOL for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

3D MOL for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

3D SDF for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

3D-SDF for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

PDB for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

3D PDB for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

SMILES for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

INCHI for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

Structure for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)

3D Structure for NP0157562 ((1r,2r,4r,5r)-5-ethenyl-2-(2-hydroxypropan-2-yl)-5-methyl-4-(prop-1-en-2-yl)cyclohexyl acetate)