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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:06 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002726

Secondary Accession Numbers

HMDB02726

Metabolite Identification

Common Name

Guggulsterone

Description

Guggulsterone is an ingredient in many nutritional supplements. Guggulsterone is a plant sterol derived from the gum resin (guggulu) of the tree Commiphora mukul. This sterol can inhibit NF-κB activation and downregulate the expression of inflammatory gene products such as COX-2 and MMP-9, which are major players in the development of arthritis. Guggulsterone also can suppress osteoclastogenesis induced by RANKL (receptor activator of NF-κB ligand), a bone-resorbing cytokine. The anti-inflammatory activity of C. mukul (guggul) has been compared with that of NSAIDs, namely phenylbutazone and ibuprofen. Guggulsterone is used to treat obesity, diabetes, hyperlipidemia, atherosclerosis, and osteoarthritis, and has been recently shown to antagonize the farnesoid X receptor and decrease the expression of bile acid-activated genes. It modulates activation of NF-kappaB, which has been closely linked with inflammatory diseases affected by guggulsterone. (PMID: 17475558 , 15322087 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 02231219352D          

 28 31  0  0  1  0            999 V2000
   21.3730  -13.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7720  -11.0022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8374  -15.1695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718  -13.8890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8573  -13.4766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2862  -13.4766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2862  -12.6517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1067  -13.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8573  -12.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718  -12.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5850  -14.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0667  -13.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1001  -14.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8442  -15.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0667  -12.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3422  -13.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2862  -11.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5481  -13.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1130  -13.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5602  -13.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3285  -15.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230  -11.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5533  -14.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1301  -11.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0284  -10.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1458  -14.2145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4290  -13.1466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.3560  -14.1327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  2  0  0  0  0
  2 22  1  0  0  0  0
  2 25  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  4 26  1  6  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 27  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 28  1  6  0  0  0
  7 10  1  0  0  0  0
  7 15  1  0  0  0  0
  7 17  1  1  0  0  0
  8 13  1  0  0  0  0
  8 16  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  2  0  0  0  0
 15 18  1  0  0  0  0
 15 22  2  0  0  0  0
 16 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END

HMDB0002726
     RDKit          3D
Guggulsterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8999   -1.1683   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.6079   -0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8705   -0.9497    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -1.0666    1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630   -0.1871    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7150    0.5499    2.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579    0.5521    2.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    1.2904    2.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    0.3279    1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7221    0.6703    0.7767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0897    2.1067    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    2.2523   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1238    1.1436   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    1.2455   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2342    0.0472   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5038    0.1559   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583   -1.3312   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1908   -1.1467    0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803   -0.2361   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9108   -0.6345   -2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -0.0974   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3506   -1.3897   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.0946   -0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.0965    0.0277 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9304    1.2810   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.2901   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -1.6539   -2.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -0.0602   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.6904    2.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966   -0.0965    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8220   -1.6752    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033    2.2931    1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939    1.2418    3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360   -0.6467    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233    0.2210    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    2.4608    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819    2.8130    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6535    2.3154   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    3.2268   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8105    2.2322    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1555   -1.8617    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7391   -1.8983   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -0.6411    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.1082    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017   -1.6700   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.5127   -2.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    0.0314   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.4469   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.8787    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -2.1296   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579   -2.0411   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -0.9859   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938    0.9119   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    1.8845   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    1.9519   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  5  1  0
 24  9  1  0
 21 10  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  1
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

  Mrv0541 02231219352D          

 28 31  0  0  1  0            999 V2000
   21.3730  -13.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7720  -11.0022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8374  -15.1695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718  -13.8890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8573  -13.4766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2862  -13.4766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2862  -12.6517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1067  -13.8946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8573  -12.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718  -12.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5850  -14.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0667  -13.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1001  -14.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8442  -15.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0667  -12.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3422  -13.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2862  -11.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5481  -13.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1130  -13.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5602  -13.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3285  -15.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230  -11.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5533  -14.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1301  -11.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0284  -10.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1458  -14.2145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4290  -13.1466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.3560  -14.1327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  2  0  0  0  0
  2 22  1  0  0  0  0
  2 25  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  4 26  1  6  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 27  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 28  1  6  0  0  0
  7 10  1  0  0  0  0
  7 15  1  0  0  0  0
  7 17  1  1  0  0  0
  8 13  1  0  0  0  0
  8 16  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  2  0  0  0  0
 15 18  1  0  0  0  0
 15 22  2  0  0  0  0
 16 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002726

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1

> <INCHI_KEY>
WOVLRQSWILBDQL-IABMEBKLSA-N

> <FORMULA>
C22H30O3

> <MOLECULAR_WEIGHT>
342.4718

> <EXACT_MASS>
342.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.539011424137044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.463078583666667

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.821002778132108

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.95529583864429

> <JCHEM_PKA_STRONGEST_BASIC>
-4.482497684517963

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
100.48159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-guggulsterone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002726
     RDKit          3D
Guggulsterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8999   -1.1683   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.6079   -0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8705   -0.9497    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -1.0666    1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630   -0.1871    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7150    0.5499    2.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579    0.5521    2.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    1.2904    2.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    0.3279    1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7221    0.6703    0.7767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0897    2.1067    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    2.2523   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1238    1.1436   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    1.2455   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2342    0.0472   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5038    0.1559   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583   -1.3312   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1908   -1.1467    0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803   -0.2361   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9108   -0.6345   -2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -0.0974   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3506   -1.3897   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.0946   -0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.0965    0.0277 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9304    1.2810   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.2901   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -1.6539   -2.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -0.0602   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.6904    2.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966   -0.0965    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8220   -1.6752    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033    2.2931    1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939    1.2418    3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360   -0.6467    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233    0.2210    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    2.4608    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819    2.8130    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6535    2.3154   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    3.2268   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8105    2.2322    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1555   -1.8617    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7391   -1.8983   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -0.6411    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.1082    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017   -1.6700   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.5127   -2.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    0.0314   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.4469   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.8787    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -2.1296   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579   -2.0411   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -0.9859   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938    0.9119   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    1.8845   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    1.9519   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  5  1  0
 24  9  1  0
 21 10  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  1
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      39.896 -24.386   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.908 -20.537   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.696 -28.316   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      34.667 -25.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.334 -25.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.001 -25.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.001 -23.617   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.933 -25.937   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.334 -23.617   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.667 -22.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.692 -27.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.458 -25.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.920 -27.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.309 -28.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.458 -23.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.505 -25.068   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.001 -22.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.356 -24.386   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.944 -24.397   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.046 -25.881   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.480 -28.387   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.936 -21.683   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.033 -27.551   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.443 -21.366   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.386 -19.074   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      35.739 -26.534   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      34.401 -24.540   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      36.131 -26.381   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   22   25                                                       
CONECT    3   23                                                            
CONECT    4    5    6   11   26                                             
CONECT    5    4    8    9   27                                             
CONECT    6    4    7   12   28                                             
CONECT    7    6   10   15   17                                             
CONECT    8    5   13   16   19                                             
CONECT    9    5   10                                                       
CONECT   10    7    9                                                       
CONECT   11    4   14                                                       
CONECT   12    6   18                                                       
CONECT   13    8   14   21                                                  
CONECT   14   11   13                                                       
CONECT   15    7   18   22                                                  
CONECT   16    8   20                                                       
CONECT   17    7                                                            
CONECT   18    1   12   15                                                  
CONECT   19    8                                                            
CONECT   20   16   23                                                       
CONECT   21   13   23                                                       
CONECT   22    2   15   24                                                  
CONECT   23    3   20   21                                                  
CONECT   24   22                                                            
CONECT   25    2                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0002726
HETATM    1  C1  UNL     1       4.900  -1.168  -1.733  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.907  -1.608  -0.806  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.870  -0.950   0.415  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.006  -1.067   1.396  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.863  -0.187   0.806  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.715   0.550   2.058  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.558   0.552   2.995  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.396   1.290   2.021  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.644   0.328   1.140  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.722   0.670   0.777  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.090   2.107   0.687  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.155   2.252  -0.409  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.124   1.144  -0.368  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.404   1.245  -0.146  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.234   0.047  -0.138  1.00  0.00           C  
HETATM   16  O3  UNL     1      -6.504   0.156  -0.237  1.00  0.00           O  
HETATM   17  C14 UNL     1      -4.658  -1.331  -0.015  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.191  -1.147   0.401  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.580  -0.236  -0.605  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.911  -0.634  -2.019  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.081  -0.097  -0.504  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.351  -1.390  -0.462  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.125  -1.095  -0.750  1.00  0.00           C  
HETATM   24  C21 UNL     1       1.625   0.096   0.028  1.00  0.00           C  
HETATM   25  C22 UNL     1       1.930   1.281  -0.817  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.926  -1.290  -1.306  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.778  -1.654  -2.713  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.754  -0.060  -1.882  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.632  -1.690   2.240  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.397  -0.097   1.701  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.822  -1.675   0.916  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.503   2.293   1.606  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.994   1.242   3.038  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.636  -0.647   1.721  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.423   0.221   1.546  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.619   2.461   1.621  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.282   2.813   0.527  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.654   2.315  -1.395  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.651   3.227  -0.232  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.811   2.232   0.026  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.155  -1.862   0.827  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.739  -1.898  -0.961  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.261  -0.641   1.406  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.688  -2.108   0.531  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.602  -1.670  -2.208  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.976  -0.513  -2.268  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.324   0.031  -2.694  1.00  0.00           H  
HETATM   48  H23 UNL     1      -0.769   0.447  -1.419  1.00  0.00           H  
HETATM   49  H24 UNL     1      -0.474  -1.879   0.533  1.00  0.00           H  
HETATM   50  H25 UNL     1      -0.693  -2.130  -1.207  1.00  0.00           H  
HETATM   51  H26 UNL     1       1.658  -2.041  -0.444  1.00  0.00           H  
HETATM   52  H27 UNL     1       1.233  -0.986  -1.827  1.00  0.00           H  
HETATM   53  H28 UNL     1       2.494   0.912  -1.711  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.115   1.884  -1.177  1.00  0.00           H  
HETATM   55  H30 UNL     1       2.644   1.952  -0.258  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    5    5
CONECT    4   29   30   31
CONECT    5    6   24
CONECT    6    7    7    8
CONECT    8    9   32   33
CONECT    9   10   24   34
CONECT   10   11   21   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   14   19
CONECT   14   15   40
CONECT   15   16   16   17
CONECT   17   18   41   42
CONECT   18   19   43   44
CONECT   19   20   21
CONECT   20   45   46   47
CONECT   21   22   48
CONECT   22   23   49   50
CONECT   23   24   51   52
CONECT   24   25
CONECT   25   53   54   55
END

HMDB0002726
     RDKit          3D
Guggulsterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8999   -1.1683   -1.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.6079   -0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8705   -0.9497    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -1.0666    1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630   -0.1871    0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7150    0.5499    2.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579    0.5521    2.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    1.2904    2.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    0.3279    1.1397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7221    0.6703    0.7767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0897    2.1067    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554    2.2523   -0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1238    1.1436   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    1.2455   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2342    0.0472   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5038    0.1559   -0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583   -1.3312   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1908   -1.1467    0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5803   -0.2361   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9108   -0.6345   -2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -0.0974   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3506   -1.3897   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251   -1.0946   -0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.0965    0.0277 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9304    1.2810   -0.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9265   -1.2901   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -1.6539   -2.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -0.0602   -1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -1.6904    2.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966   -0.0965    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8220   -1.6752    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033    2.2931    1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939    1.2418    3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6360   -0.6467    1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233    0.2210    1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6195    2.4608    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2819    2.8130    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6535    2.3154   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    3.2268   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8105    2.2322    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1555   -1.8617    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7391   -1.8983   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2610   -0.6411    1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.1082    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017   -1.6700   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -0.5127   -2.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    0.0314   -2.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7689    0.4469   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.8787    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -2.1296   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6579   -2.0411   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -0.9859   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938    0.9119   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147    1.8845   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    1.9519   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24  5  1  0
 24  9  1  0
 21 10  1  0
 19 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  1
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8XI,9xi,14xi,17E)-20-methoxypregna-4,17-diene-3,16-dione	HMDB
20-Methoxy-4,17(20)e-pregnadiene-3,16-dione	HMDB
4,17(20)-Pregnadiene-3,16-dione	HMDB
Guggulsterone-m	HMDB

Chemical Formula

C₂₂H₃₀O₃

Average Molecular Weight

342.4718

Monoisotopic Molecular Weight

342.219494826

IUPAC Name

(1R,2R,10S,11S,14E,15S)-14-(1-methoxyethylidene)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,13-dione

Traditional Name

(Z)-guggulsterone

CAS Registry Number

95975-55-6

SMILES

[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C22H30O3/c1-13(25-4)20-19(24)12-18-16-6-5-14-11-15(23)7-9-21(14,2)17(16)8-10-22(18,20)3/h11,16-18H,5-10,12H2,1-4H3/b20-13-/t16-,17+,18-,21-,22-/m0/s1

InChI Key

WOVLRQSWILBDQL-IABMEBKLSA-N

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
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
16-oxosteroid
Delta-4-steroid
Cyclohexenone
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002726)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0002726)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002726)

Source

Endogenous

Endogenous (HMDB: HMDB0002726)

Animal

Animal (HMDB: HMDB0002726)

Exogenous

Food

Food (HMDB: HMDB0002726)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002726)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002726)

Molecular messenger

Hormone (HMDB: HMDB0002726)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002726)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	13.75 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0099 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	18.96	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.48 m³·mol⁻¹	ChemAxon
Polarizability	39.54 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	217.858	30932474
DeepCCS	[M+Na]+	193.806	30932474
AllCCS	[M+H]+	185.8	32859911
AllCCS	[M+H-H2O]+	183.1	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.1	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	192.3	32859911
AllCCS	[M+HCOO]-	193.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guggulsterone	[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C	3781.5	Standard polar	33892256
Guggulsterone	[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C	2749.2	Standard non polar	33892256
Guggulsterone	[H][C@@]12CC(=O)\C(=C(/C)OC)[C@@]1(C)CC[C@]1([H])[C@]2([H])CCC2=CC(=O)CC[C@]12C	3024.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Guggulsterone,1TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	3029.4	Semi standard non polar	33892256
Guggulsterone,1TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	2730.5	Standard non polar	33892256
Guggulsterone,1TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	3315.5	Standard polar	33892256
Guggulsterone,1TMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	2972.9	Semi standard non polar	33892256
Guggulsterone,1TMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	2787.4	Standard non polar	33892256
Guggulsterone,1TMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3312.6	Standard polar	33892256
Guggulsterone,2TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	2950.2	Semi standard non polar	33892256
Guggulsterone,2TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	2839.5	Standard non polar	33892256
Guggulsterone,2TMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3343.2	Standard polar	33892256
Guggulsterone,1TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	3260.4	Semi standard non polar	33892256
Guggulsterone,1TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	2934.4	Standard non polar	33892256
Guggulsterone,1TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C	3452.6	Standard polar	33892256
Guggulsterone,1TBDMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3214.5	Semi standard non polar	33892256
Guggulsterone,1TBDMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3008.3	Standard non polar	33892256
Guggulsterone,1TBDMS,isomer #2	CO/C(C)=C1/C(=O)C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3446.1	Standard polar	33892256
Guggulsterone,2TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3402.9	Semi standard non polar	33892256
Guggulsterone,2TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3216.9	Standard non polar	33892256
Guggulsterone,2TBDMS,isomer #1	CO/C(C)=C1/C(O[Si](C)(C)C(C)(C)C)=C[C@H]2[C@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@@H]3CC[C@]12C	3555.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Guggulsterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0200-0459000000-ee86b2088f6ad3cdf31d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guggulsterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 10V, Positive-QTOF	splash10-0006-1039000000-952388fe83cbda93ea21	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 20V, Positive-QTOF	splash10-00ov-1279000000-5728b5f9167d8cb78890	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 40V, Positive-QTOF	splash10-0a6r-9083000000-b8990378d7107ffa738d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 10V, Negative-QTOF	splash10-0006-0029000000-5338c79160c73600c4b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 20V, Negative-QTOF	splash10-000f-0069000000-32d9482c72cfc85099ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 40V, Negative-QTOF	splash10-00kf-2090000000-69c0d68769a4ff1f7ec6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 10V, Negative-QTOF	splash10-0006-0019000000-91e1f5ec96b7e91e6084	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 20V, Negative-QTOF	splash10-001l-0089000000-b763db8304fe27efa3a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 40V, Negative-QTOF	splash10-001u-0090000000-a41631240a8cd7b56409	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 10V, Positive-QTOF	splash10-0006-0009000000-2538c557c24fab48c6bf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 20V, Positive-QTOF	splash10-01r7-1389000000-a0a95688ed26bb666896	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guggulsterone 40V, Positive-QTOF	splash10-0006-9430000000-3ba9301f7512c0faae5c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023055

KNApSAcK ID

C00047241

Chemspider ID

558777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Guggulsterone

METLIN ID

Not Available

PubChem Compound

643658

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1903101

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Khanna D, Sethi G, Ahn KS, Pandey MK, Kunnumakkara AB, Sung B, Aggarwal A, Aggarwal BB: Natural products as a gold mine for arthritis treatment. Curr Opin Pharmacol. 2007 Jun;7(3):344-51. Epub 2007 May 1. [PubMed:17475558 ]
Shishodia S, Aggarwal BB: Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis. J Biol Chem. 2004 Nov 5;279(45):47148-58. Epub 2004 Aug 17. [PubMed:15322087 ]

Showing metabocard for Guggulsterone (HMDB0002726)

MOL for HMDB0002726 (Guggulsterone)

3D MOL for HMDB0002726 (Guggulsterone)

3D SDF for HMDB0002726 (Guggulsterone)

3D-SDF for HMDB0002726 (Guggulsterone)

PDB for HMDB0002726 (Guggulsterone)

3D PDB for HMDB0002726 (Guggulsterone)

SMILES for HMDB0002726 (Guggulsterone)

INCHI for HMDB0002726 (Guggulsterone)

Structure for HMDB0002726 (Guggulsterone)

3D Structure for HMDB0002726 (Guggulsterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra