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Showing NP-Card for Ergost-4-en-3-one (NP0049186)

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Record Information
Version2.0
Created at2022-03-17 21:08:28 UTC
Updated at2022-03-17 21:08:28 UTC
NP-MRD IDNP0049186
Secondary Accession NumbersNone
Natural Product Identification
Common NameErgost-4-en-3-one
DescriptionErgost-4-en-3-one belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Ergost-4-en-3-one is found in Arabidopsis thaliana, Cannabis sativa, Pellia epiphylla, Tillandsia recurvata and Zanthoxylum wutaiense. Ergost-4-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049186 (Ergost-4-en-3-one)


  Mrv0541 02241215232D          

 33 36  0  0  0  0            999 V2000
   11.7616   -3.8310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7616   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3326   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9037   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1892   -5.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9037   -3.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182   -3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3326   -3.8310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3326   -3.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -3.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0471   -2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7616   -2.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2606   -2.3385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4760   -2.5935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4760   -3.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2606   -3.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7455   -3.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2606   -1.5135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9751   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6896   -1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4040   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1185   -1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8330   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1185   -2.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -4.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7616   -3.0060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4760   -4.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4760   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0575   -2.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5461   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4040   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17  1  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 12 27  1  6  0  0  0
  1 28  1  1  0  0  0
 17 29  1  6  0  0  0
 16 30  1  1  0  0  0
 15 31  1  6  0  0  0
 20 32  1  6  0  0  0
 23 33  1  0  0  0  0
M  END
Download

3D MOL for NP0049186 (Ergost-4-en-3-one)

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3D SDF for NP0049186 (Ergost-4-en-3-one)

  Mrv0541 02241215232D          

 33 36  0  0  0  0            999 V2000
   11.7616   -3.8310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7616   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3326   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182   -5.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9037   -4.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1892   -5.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9037   -3.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6182   -3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3326   -3.8310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3326   -3.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -3.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0471   -2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7616   -2.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2606   -2.3385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4760   -2.5935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4760   -3.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2606   -3.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7455   -3.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2606   -1.5135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9751   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6896   -1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4040   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1185   -1.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8330   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1185   -2.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0471   -4.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7616   -3.0060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4760   -4.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4760   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0575   -2.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5461   -1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4040   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17  1  1  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 12 27  1  6  0  0  0
  1 28  1  1  0  0  0
 17 29  1  6  0  0  0
 16 30  1  1  0  0  0
 15 31  1  6  0  0  0
 20 32  1  6  0  0  0
 23 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19?,20-,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
QQIOPZFVTIHASB-SRGSQMPJSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.6093331899875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-14-[(2R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
6.40

> <JCHEM_LOGP>
7.967154075000002

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.087826253912493

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817440235063846

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
124.11369999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14R,15R)-14-[(2R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049186 (Ergost-4-en-3-one)
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PDB for NP0049186 (Ergost-4-en-3-one)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.955  -7.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.955  -8.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.621  -9.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.288  -8.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.954  -9.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.620  -8.691   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.287  -9.461   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.620  -7.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.954  -6.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.288  -7.151   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.288  -5.611   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.621  -6.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.621  -4.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.955  -4.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.753  -4.365   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.289  -4.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.289  -6.381   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.753  -6.857   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.658  -5.611   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.753  -2.825   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.087  -2.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.421  -2.825   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.754  -2.055   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.088  -2.825   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.422  -2.055   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.088  -4.365   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      20.621  -7.921   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      21.955  -5.611   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      23.289  -7.921   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      23.289  -3.301   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      26.241  -3.967   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      23.419  -2.055   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.754  -0.515   0.000  0.00  0.00           C+0
CONECT    1   17    2   12   28                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11   12                                             
CONECT   11   10                                                            
CONECT   12   10    1   13   27                                             
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15   16   19   20   31                                             
CONECT   16   14   15   17   30                                             
CONECT   17    1   18   16   29                                             
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   15   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   12                                                            
CONECT   28    1                                                            
CONECT   29   17                                                            
CONECT   30   16                                                            
CONECT   31   15                                                            
CONECT   32   20                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

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3D PDB for NP0049186 (Ergost-4-en-3-one)
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SMILES for NP0049186 (Ergost-4-en-3-one)
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(C)C(C)C
Download
INCHI for NP0049186 (Ergost-4-en-3-one)
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19?,20-,23+,24-,25+,26+,27+,28-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC28H46O
Average Mass398.6642 Da
Monoisotopic Mass398.35487 Da
IUPAC Name(1S,2R,10S,11S,14R,15R)-14-[(2R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14R,15R)-14-[(2R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(C)C(C)C
InChI Identifier
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19?,20-,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyQQIOPZFVTIHASB-SRGSQMPJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
Cannabis sativaLOTUS Database
Glycine maxFooDB
Pellia epiphyllaLOTUS Database
Tillandsia recurvataLOTUS Database
Zanthoxylum wutaiensePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a  derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassErgostane steroids  
Direct ParentErgosterols and derivatives  
Alternative Parents
Substituents
  • Ergosterol-skeleton
    • 

  • Oxosteroid
    • 

  • 3-oxosteroid
    • 

  • 3-oxo-delta-4-steroid
    • 

  • Delta-4-steroid
    • 

  • Cyclohexenone
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.4ALOGPS
logP7.97ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.11 m³·mol⁻¹ChemAxon
Polarizability51.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018054  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14537344  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available