NP-MRD: Showing NP-Card for (1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione (NP0295601)

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Record Information

Version

2.0

Created at

2022-09-10 04:40:15 UTC

Updated at

2022-09-10 04:40:15 UTC

NP-MRD ID

NP0295601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione

Description

Guggulsterone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. (1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione is found in Commiphora wightii. (1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione was first documented in 2022 (PMID: 35745024). Based on a literature review a small amount of articles have been published on Guggulsterone (PMID: 36014345) (PMID: 35909996) (PMID: 35889266) (PMID: 35714682).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.5297    1.9003   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410    0.4425   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459   -0.2351   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527   -1.7026   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4311   -2.4725    0.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999   -2.0793   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640   -0.9643    0.6260 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1014   -0.9355    0.5017 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5763   -2.3448    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101   -2.3859   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -1.1487   -0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0242   -1.1488    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7464    0.1257    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903    0.2196    0.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833    1.3365    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4843    1.0105    0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1487    0.2181   -0.2587 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7063    0.8918   -1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6829   -0.0093   -0.4959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0124    1.2892   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5098    1.1354   -0.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1089    0.2846    0.3005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2752    1.0924    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1510    2.2361   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0629    2.4231    0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958    2.2881   -0.5108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4690   -0.0870   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937   -1.9840   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8415   -3.0704    0.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -1.2254    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741   -0.7135    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -2.7959   -0.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916   -2.9667    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -3.2132    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1140   -2.6618   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5673   -2.0603    0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    2.1732    0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910    1.6365    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830    0.4100    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    1.9624    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595    0.6876   -1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213    0.5290   -2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595    1.9846   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6210   -0.5291   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188    1.7397   -1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1924    2.0446    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087    2.1741   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.7196   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2777    0.9461    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769    2.1431    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639    0.6897    2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  3  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  1
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  6
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END


  Mrv1652309102206402D          

 23 26  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0295601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C(=O)C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4-/t15-,17+,18-,20-,21-/m0/s1

> <INCHI_KEY>
WDXRGPWQVHZTQJ-PXYKUDORSA-N

> <FORMULA>
C21H28O2

> <MOLECULAR_WEIGHT>
312.453

> <EXACT_MASS>
312.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.68631395928563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,10S,11S,14E,15R)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione

> <JCHEM_LOGP>
4.254959283333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.04212479887441

> <JCHEM_PKA_STRONGEST_BASIC>
-4.537711695904219

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
93.60709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10S,11S,14E,15R)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    3    7   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
(e)-Guggulsterone	MeSH
Pregna-4,17-diene-3,16-dione, (17E)-isomer	MeSH
(Z)-Guggulsterone	MeSH
Pregna-4,17-diene-3,16-dione	MeSH
Pregna-4,17-diene-3,16-dione, (17Z)-isomer	MeSH

Chemical Formula

C₂₁H₂₈O₂

Average Mass

312.4530 Da

Monoisotopic Mass

312.20893 Da

IUPAC Name

(1R,2R,10S,11S,14E,15R)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione

Traditional Name

(1R,2R,10S,11S,14E,15R)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione

CAS Registry Number

Not Available

SMILES

C\C=C1\C(=O)C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@@]12C

InChI Identifier

InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4-/t15-,17+,18-,20-,21-/m0/s1

InChI Key

WDXRGPWQVHZTQJ-PXYKUDORSA-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

Species Name	Source	Reference
Commiphora wightii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
Oxosteroid
16-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 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	4.25	ChemAxon
pKa (Strongest Acidic)	19.04	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.61 m³·mol⁻¹	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	4	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

C00047241

Chemspider ID

32821945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guggulsterone

METLIN ID

Not Available

PubChem Compound

122173093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ulrich J, Stiltz S, St-Gelais A, El Gaafary M, Simmet T, Syrovets T, Schmiech M: Phytochemical Composition of Commiphora Oleogum Resins and Their Cytotoxicity against Skin Cancer Cells. Molecules. 2022 Jun 17;27(12):3903. doi: 10.3390/molecules27123903. [PubMed:35745024 ]
Gupta M, Ghufran SM, Kausar T, Ali R, Biswas S, Nayeem SM, Ishrat R, Ali S, Ahmad A, Rather IA, Sarwat M: Z-Guggulsterone Is a Potential Lead Molecule of Dawa-ul-Kurkum against Hepatocellular Carcinoma. Molecules. 2022 Aug 11;27(16):5104. doi: 10.3390/molecules27165104. [PubMed:36014345 ]
Priya SS, Jha A, Satish Kumar RC, Sabarathinam S: The role of guggulsterone on the NF-kappaB pathway in inflammatory bowel disease: preclinical evidence. Future Sci OA. 2022 Jun 27;8(6):FSO803. doi: 10.2144/fsoa-2022-0020. eCollection 2022 Jul. [PubMed:35909996 ]
Taylor E, Kim Y, Zhang K, Chau L, Nguyen BC, Rayalam S, Wang X: Antiaging Mechanism of Natural Compounds: Effects on Autophagy and Oxidative Stress. Molecules. 2022 Jul 8;27(14):4396. doi: 10.3390/molecules27144396. [PubMed:35889266 ]
Liu J, Lin Y, Yang Y, Guo Y, Shang Y, Zhou B, Liu T, Fan J, Wei C: Z-Guggulsterone attenuates cognitive defects and decreases neuroinflammation in APPswe/PS1dE9 mice through inhibiting the TLR4 signaling pathway. Biochem Pharmacol. 2022 Aug;202:115149. doi: 10.1016/j.bcp.2022.115149. Epub 2022 Jun 14. [PubMed:35714682 ]
LOTUS database [Link]

Showing NP-Card for (1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione (NP0295601)

MOL for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

3D MOL for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

3D SDF for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

3D-SDF for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

PDB for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

3D PDB for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

SMILES for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

INCHI for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

Structure for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)

3D Structure for NP0295601 ((1e,3as,3bs,9ar,9br,11ar)-1-ethylidene-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-dione)