NP-MRD: Showing NP-Card for 2-Ketoepimanool (NP0052026)

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Record Information

Version

2.0

Created at

2022-04-27 23:12:55 UTC

Updated at

2022-04-27 23:12:55 UTC

NP-MRD ID

NP0052026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Ketoepimanool

Description

2-Ketoepimanool belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-Ketoepimanool is found in Nicotiana glutinosa. Based on a literature review very few articles have been published on 2-Ketoepimanool.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
    5.1764   -0.6180   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3390   -0.2788   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966    0.9176   -1.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3192    2.0343   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0233    1.3364   -2.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232    0.6776   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5161   -0.4218   -0.9069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202   -0.8713   -0.1733 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5189   -1.3843    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094   -1.8479    1.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005   -1.3928    2.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572   -1.3309    1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0485   -0.7131    0.2028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3668   -0.1054   -0.0695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4034   -1.2233    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031    1.0355    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959    0.2850   -1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3373    1.1547   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    2.2481   -2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    0.6653   -1.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    0.1294   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6070    1.2573    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -0.0389    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -1.4986   -0.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -0.8909   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9896    3.0427   -1.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746    1.8817   -1.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2281    1.9991    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258    0.7825   -3.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550    1.6540   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    0.5227    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -0.1085   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618   -1.3220   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7408   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5366   -1.8523    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -2.2300    2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -0.6197    2.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5366   -2.3649    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427   -2.3520    1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232   -0.7482    2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -1.5831   -0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668   -1.3610    1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9865   -2.1531   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474   -0.9409   -0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9169    1.1506    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    0.9136    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4017    2.0262    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418   -0.6141   -2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    0.8634   -1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685    1.4997   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868   -0.1877   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    2.2388    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3992    1.4029    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    1.0752    1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  6
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  1
  3  2  1  0
  2  1  2  3
 21  8  1  0
 21 13  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  6
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652304282201122D          

 22 23  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  2  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
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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    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  1  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  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
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  1  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  6  0  0  0
 15 19  1  6  0  0  0
  6 20  1  1  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@](O)(CC[C@H]1C(=C)CC[C@H]2C(C)(C)CC(=O)C[C@]12C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-7-19(5,22)11-10-16-14(2)8-9-17-18(3,4)12-15(21)13-20(16,17)6/h7,16-17,22H,1-2,8-13H2,3-6H3/t16-,17-,19+,20+/m0/s1

> <INCHI_KEY>
UPIJHQOLJKUYGG-RAUXBKROSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.26938838042765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8S,8aS)-8-[(3S)-3-hydroxy-3-methylpent-4-en-1-yl]-4,4,8a-trimethyl-7-methylidene-decahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
4.125201877666665

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.327628325087332

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3432949599623898

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
91.7197

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ketoepimanool

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   21   22                                             
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8   20                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5                                                       
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18   19                                             
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20    6                                                            
CONECT   21    4                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₂

Average Mass

304.4740 Da

Monoisotopic Mass

304.24023 Da

IUPAC Name

(4aS,8S,8aS)-8-[(3S)-3-hydroxy-3-methylpent-4-en-1-yl]-4,4,8a-trimethyl-7-methylidene-decahydronaphthalen-2-one

Traditional Name

2-ketoepimanool

CAS Registry Number

Not Available

SMILES

C[C@](O)(CC[C@H]1C(=C)CC[C@H]2C(C)(C)CC(=O)C[C@]12C)C=C

InChI Identifier

InChI=1S/C20H32O2/c1-7-19(5,22)11-10-16-14(2)8-9-17-18(3,4)12-15(21)13-20(16,17)6/h7,16-17,22H,1-2,8-13H2,3-6H3/t16-,17-,19+,20+/m0/s1

InChI Key

UPIJHQOLJKUYGG-RAUXBKROSA-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
Nicotiana glutinosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diterpenoid (CHEBI:1182 )
Labdanes (C09124 )

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	3.92	ALOGPS
logP	4.13	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	18.33	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.72 m³·mol⁻¹	ChemAxon
Polarizability	36.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00003449

Chemspider ID

390600

KEGG Compound ID

C09124

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Ketoepimanool (NP0052026)

MOL for NP0052026 (2-Ketoepimanool)

3D MOL for NP0052026 (2-Ketoepimanool)

3D SDF for NP0052026 (2-Ketoepimanool)

3D-SDF for NP0052026 (2-Ketoepimanool)

PDB for NP0052026 (2-Ketoepimanool)

3D PDB for NP0052026 (2-Ketoepimanool)

SMILES for NP0052026 (2-Ketoepimanool)

INCHI for NP0052026 (2-Ketoepimanool)

Structure for NP0052026 (2-Ketoepimanool)

3D Structure for NP0052026 (2-Ketoepimanool)