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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:07 UTC

HMDB ID

HMDB0000937

Secondary Accession Numbers

HMDB00937

Metabolite Identification

Common Name

Stigmasterol

Description

Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism.

Structure

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


  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8380 9999.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6956 9997.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5507 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2635 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1240 9998.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9998.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9997.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.1240 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8385 9998.5654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.263810000.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9999.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5493 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2638 9998.5744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5507 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2652 9997.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9783 9999.8118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9783 9998.9868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7629 9998.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2478 9999.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.762910000.0668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.762910000.8918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.478610001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192210000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.907910001.3043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.623610000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610000.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.907910002.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610002.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.478610000.4793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
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 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
M  END

HMDB0000937
     RDKit          3D
Stigmasterol
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.9389    1.6838   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5555    1.5718    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152    0.9911   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334    1.0149    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.0203    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.0573    1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0007    1.2328    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -0.2189    0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1959   -1.5793   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4932   -1.0330   -0.3795 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.2880    1.0037    1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8380 9999.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9999.2635 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 9996.4095 9997.7403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 34  1  6  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000937

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
HCXVJBMSMIARIN-PHZDYDNGSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.55229580663386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
6.95

> <JCHEM_LOGP>
7.482555135333334

> <ALOGPS_LOGS>
-7.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.88269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.73e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000937
     RDKit          3D
Stigmasterol
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.9389    1.6838   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5555    1.5718    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152    0.9911   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334    1.0149    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.0203    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.0573    1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0007    1.2328    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -0.2189    0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1959   -1.5793   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175   -2.0768   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249   -0.8520   -0.4899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4932   -1.0330   -0.3795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0404   -1.2269   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599   -0.6315   -1.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1373   -0.0695   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4568    0.4861   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0764    1.3660   -0.4477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4572    1.4235   -0.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7805    0.8618    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    1.0037    1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6108   -0.0406    0.3226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7603   -1.3796    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1228    0.1985    0.1807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4728    0.7251    1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    1.0215    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -0.2883    0.7627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5569   -1.2971    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7818   -0.3180   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9602   -0.3362   -2.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140   -1.4282   -0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4948    0.7616   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0283    2.4323   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5192    2.2126    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2199    2.6292    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5862    1.1024    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3434    1.7242   -1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9950    1.9484    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203   -0.9040   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060   -0.8274    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3802    0.9663    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    1.4189    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    2.1769    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0231    0.5124   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -1.5211   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7149   -2.2911    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962   -2.9346   -0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -2.4374   -1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -0.1196   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -1.9680    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438   -2.3109   -2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3400   -0.7465   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457   -0.6521   -3.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3740    1.0741   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1525   -0.3456   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7066    2.4290   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7215    1.7063   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0911   -0.2007    0.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3573    1.4771    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458    2.0287    0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0748    0.7693    2.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6678   -1.4725    1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4728    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7733   -2.1786    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0245    0.9976   -0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9897    1.6502    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5394    0.0198    2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0760    1.5865    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058    1.6391    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -1.9099    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -0.8301    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -2.0169    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -0.5849   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7896   -1.0106   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3244    0.6535   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979   -0.8361   -3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684   -1.1470    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4915   -2.3651   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1069   -1.7151   -0.0582 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
  4  5  2  0
  5  6  1  0
  6  7  1  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  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  6
 12 49  1  1
 13 50  1  0
 13 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  6
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.6228667.865   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6318665.538   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6328661.672   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.9618663.232   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8665.2928665.538   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6228663.232   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8661.2988664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9648663.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9648662.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.2988661.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6328662.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6328663.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2928667.086   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9598666.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598664.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2928664.006   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9618661.679   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.2958662.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6268666.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6268664.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0918664.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.9968665.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0918666.791   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918668.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4278669.101   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.7598668.331   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.0958669.101   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8673.4318668.331   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8674.7638669.101   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8673.4318666.791   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8672.0958670.641   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8673.4318671.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.7598669.101   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8669.4278667.561   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   12                                                            
CONECT    3    9                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12    7   11    2   15                                             
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4   12                                             
CONECT   16   15   18    5   20                                             
CONECT   17   18   11                                                       
CONECT   18   17   16                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21   16    6                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   34   19   22                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0000937
HETATM    1  C1  UNL     1       7.939   1.684  -0.105  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.555   1.572   0.402  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.515   0.991  -0.469  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.233   1.015   0.300  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.413   0.020   0.407  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.120   0.057   1.188  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.001   1.233   2.069  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.032  -0.219   0.238  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.196  -1.579  -0.415  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.217  -2.077  -0.733  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.025  -0.852  -0.490  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.493  -1.033  -0.379  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.040  -1.227  -1.779  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.360  -0.631  -1.987  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.137  -0.070  -1.069  1.00  0.00           C  
HETATM   16  C16 UNL     1      -6.457   0.486  -1.473  1.00  0.00           C  
HETATM   17  C17 UNL     1      -7.076   1.366  -0.448  1.00  0.00           C  
HETATM   18  O1  UNL     1      -8.457   1.423  -0.590  1.00  0.00           O  
HETATM   19  C18 UNL     1      -6.780   0.862   0.954  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.288   1.004   1.143  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.611  -0.041   0.323  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.760  -1.380   1.020  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.123   0.199   0.181  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.473   0.725   1.411  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.018   1.021   1.015  1.00  0.00           C  
HETATM   26  C25 UNL     1      -0.363  -0.288   0.763  1.00  0.00           C  
HETATM   27  C26 UNL     1      -0.557  -1.297   1.850  1.00  0.00           C  
HETATM   28  C27 UNL     1       5.782  -0.318  -1.109  1.00  0.00           C  
HETATM   29  C28 UNL     1       6.960  -0.336  -2.034  1.00  0.00           C  
HETATM   30  C29 UNL     1       6.014  -1.428  -0.086  1.00  0.00           C  
HETATM   31  H1  UNL     1       8.495   0.762  -0.263  1.00  0.00           H  
HETATM   32  H2  UNL     1       8.028   2.432  -0.946  1.00  0.00           H  
HETATM   33  H3  UNL     1       8.519   2.213   0.721  1.00  0.00           H  
HETATM   34  H4  UNL     1       6.220   2.629   0.636  1.00  0.00           H  
HETATM   35  H5  UNL     1       6.586   1.102   1.430  1.00  0.00           H  
HETATM   36  H6  UNL     1       5.343   1.724  -1.308  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.995   1.948   0.798  1.00  0.00           H  
HETATM   38  H8  UNL     1       3.620  -0.904  -0.076  1.00  0.00           H  
HETATM   39  H9  UNL     1       2.206  -0.827   1.867  1.00  0.00           H  
HETATM   40  H10 UNL     1       1.380   0.966   2.955  1.00  0.00           H  
HETATM   41  H11 UNL     1       3.027   1.419   2.512  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.723   2.177   1.594  1.00  0.00           H  
HETATM   43  H13 UNL     1       1.023   0.512  -0.600  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.756  -1.521  -1.368  1.00  0.00           H  
HETATM   45  H15 UNL     1       1.715  -2.291   0.270  1.00  0.00           H  
HETATM   46  H16 UNL     1      -0.496  -2.935  -0.101  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.261  -2.437  -1.786  1.00  0.00           H  
HETATM   48  H18 UNL     1      -0.778  -0.120  -1.304  1.00  0.00           H  
HETATM   49  H19 UNL     1      -2.750  -1.968   0.166  1.00  0.00           H  
HETATM   50  H20 UNL     1      -3.044  -2.311  -2.049  1.00  0.00           H  
HETATM   51  H21 UNL     1      -2.340  -0.746  -2.513  1.00  0.00           H  
HETATM   52  H22 UNL     1      -4.746  -0.652  -3.007  1.00  0.00           H  
HETATM   53  H23 UNL     1      -6.374   1.074  -2.431  1.00  0.00           H  
HETATM   54  H24 UNL     1      -7.153  -0.346  -1.711  1.00  0.00           H  
HETATM   55  H25 UNL     1      -6.707   2.429  -0.518  1.00  0.00           H  
HETATM   56  H26 UNL     1      -8.721   1.706  -1.496  1.00  0.00           H  
HETATM   57  H27 UNL     1      -7.091  -0.201   0.960  1.00  0.00           H  
HETATM   58  H28 UNL     1      -7.357   1.477   1.672  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.946   2.029   0.882  1.00  0.00           H  
HETATM   60  H30 UNL     1      -5.075   0.769   2.219  1.00  0.00           H  
HETATM   61  H31 UNL     1      -5.668  -1.473   1.625  1.00  0.00           H  
HETATM   62  H32 UNL     1      -3.912  -1.473   1.755  1.00  0.00           H  
HETATM   63  H33 UNL     1      -4.773  -2.179   0.269  1.00  0.00           H  
HETATM   64  H34 UNL     1      -3.025   0.998  -0.612  1.00  0.00           H  
HETATM   65  H35 UNL     1      -2.990   1.650   1.714  1.00  0.00           H  
HETATM   66  H36 UNL     1      -2.539   0.020   2.241  1.00  0.00           H  
HETATM   67  H37 UNL     1      -1.076   1.586   0.067  1.00  0.00           H  
HETATM   68  H38 UNL     1      -0.606   1.639   1.794  1.00  0.00           H  
HETATM   69  H39 UNL     1       0.371  -1.910   1.903  1.00  0.00           H  
HETATM   70  H40 UNL     1      -0.788  -0.830   2.847  1.00  0.00           H  
HETATM   71  H41 UNL     1      -1.381  -2.017   1.670  1.00  0.00           H  
HETATM   72  H42 UNL     1       4.884  -0.585  -1.713  1.00  0.00           H  
HETATM   73  H43 UNL     1       7.790  -1.011  -1.666  1.00  0.00           H  
HETATM   74  H44 UNL     1       7.324   0.653  -2.342  1.00  0.00           H  
HETATM   75  H45 UNL     1       6.698  -0.836  -3.023  1.00  0.00           H  
HETATM   76  H46 UNL     1       5.768  -1.147   0.936  1.00  0.00           H  
HETATM   77  H47 UNL     1       5.491  -2.365  -0.341  1.00  0.00           H  
HETATM   78  H48 UNL     1       7.107  -1.715  -0.058  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   28   36
CONECT    4    5    5   37
CONECT    5    6   38
CONECT    6    7    8   39
CONECT    7   40   41   42
CONECT    8    9   26   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   26   48
CONECT   12   13   23   49
CONECT   13   14   50   51
CONECT   14   15   15   52
CONECT   15   16   21
CONECT   16   17   53   54
CONECT   17   18   19   55
CONECT   18   56
CONECT   19   20   57   58
CONECT   20   21   59   60
CONECT   21   22   23
CONECT   22   61   62   63
CONECT   23   24   64
CONECT   24   25   65   66
CONECT   25   26   67   68
CONECT   26   27
CONECT   27   69   70   71
CONECT   28   29   30   72
CONECT   29   73   74   75
CONECT   30   76   77   78
END

HMDB0000937
     RDKit          3D
Stigmasterol
 78 81  0  0  0  0  0  0  0  0999 V2000
    7.9389    1.6838   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5555    1.5718    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152    0.9911   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2334    1.0149    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    0.0203    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.0573    1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0007    1.2328    2.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319   -0.2189    0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1959   -1.5793   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175   -2.0768   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249   -0.8520   -0.4899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4932   -1.0330   -0.3795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0404   -1.2269   -1.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599   -0.6315   -1.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1373   -0.0695   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4568    0.4861   -1.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0764    1.3660   -0.4477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4572    1.4235   -0.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7805    0.8618    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2880    1.0037    1.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6108   -0.0406    0.3226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7603   -1.3796    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1228    0.1985    0.1807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4728    0.7251    1.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    1.0215    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -0.2883    0.7627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5569   -1.2971    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7818   -0.3180   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9602   -0.3362   -2.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140   -1.4282   -0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4948    0.7616   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0283    2.4323   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5192    2.2126    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2199    2.6292    0.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5862    1.1024    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3434    1.7242   -1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9950    1.9484    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203   -0.9040   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060   -0.8274    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3802    0.9663    2.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273    1.4189    2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    2.1769    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0231    0.5124   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -1.5211   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7149   -2.2911    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962   -2.9346   -0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -2.4374   -1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -0.1196   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -1.9680    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0438   -2.3109   -2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3400   -0.7465   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457   -0.6521   -3.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3740    1.0741   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1525   -0.3456   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7066    2.4290   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7215    1.7063   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0911   -0.2007    0.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3573    1.4771    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458    2.0287    0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0748    0.7693    2.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6678   -1.4725    1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4728    1.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7733   -2.1786    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0245    0.9976   -0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9897    1.6502    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5394    0.0198    2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0760    1.5865    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058    1.6391    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -1.9099    1.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -0.8301    2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3810   -2.0169    1.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -0.5849   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7896   -1.0106   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3244    0.6535   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6979   -0.8361   -3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684   -1.1470    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4915   -2.3651   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1069   -1.7151   -0.0582 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
  4  5  2  0
  5  6  1  0
  6  7  1  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  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  5 38  1  0
  6 39  1  1
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  6
 12 49  1  1
 13 50  1  0
 13 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  6
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,22E)-Stigmasta-5,22-dien-3-ol	ChEBI
5,22-Cholestadien-24-ethyl-3beta-ol	ChEBI
beta-Stigmasterol	ChEBI
Phytosterol	ChEBI
Poriferasterol	ChEBI
Stigmasta-5,22-dien-3beta-ol	ChEBI
(3b,22E)-Stigmasta-5,22-dien-3-ol	Generator
(3β,22E)-Stigmasta-5,22-dien-3-ol	Generator
5,22-Cholestadien-24-ethyl-3b-ol	Generator
5,22-Cholestadien-24-ethyl-3β-ol	Generator
b-Stigmasterol	Generator
β-Stigmasterol	Generator
Stigmasta-5,22-dien-3b-ol	Generator
Stigmasta-5,22-dien-3β-ol	Generator
(24S)-5,22-Stigmastadien-3b-ol	HMDB
17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol	HMDB
Stigmasta-5,22-dien-3-b-ol	HMDB
Stigmasta-5,22-dien-3-beta-ol	HMDB
Stigmasterin	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3beta-ol	HMDB
(24S)-24-Ethylcholesta-5,22-dien-3β-ol	HMDB
(24S)-5,22-Stigmastadien-3beta-ol	HMDB
(24S)-5,22-Stigmastadien-3β-ol	HMDB
(24S)-Stigmast-5,22-dien-3beta-ol	HMDB
(24S)-Stigmast-5,22-dien-3β-ol	HMDB
24-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24-Ethyl-5,22-cholestadien-3β-ol	HMDB
24beta-Ethyl-5,22-cholestadien-3beta-ol	HMDB
24β-Ethyl-5,22-cholestadien-3β-ol	HMDB
Stigmasta-5,22(E)-dien-3beta-ol	HMDB
Stigmasta-5,22(E)-dien-3β-ol	HMDB
Stigmasterol	HMDB
delta5,22-Stigmastadien-3beta-ol	HMDB
delta5-Stigmasterol	HMDB
Δ5,22-Stigmastadien-3β-ol	HMDB
Δ5-Stigmasterol	HMDB

Chemical Formula

C₂₉H₄₈O

Average Molecular Weight

412.702

Monoisotopic Molecular Weight

412.370516166

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

83-48-7

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

HCXVJBMSMIARIN-PHZDYDNGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:28824 )
phytosterols (CHEBI:28824 )
stigmastane (C05442 )
Stigmasterols and C24-ethyl derivatives (C05442 )
Stigmastane and derivatives (C05442 )
Stigmasterols and C24-ethyl derivatives (LMST01040123 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.7e-05 g/L	ALOGPS
logP	6.95	ALOGPS
logP	7.48	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	53.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.574	31661259
DarkChem	[M-H]-	199.955	31661259
AllCCS	[M+H]+	208.771	32859911
AllCCS	[M-H]-	205.341	32859911
DeepCCS	[M-2H]-	241.64	30932474
DeepCCS	[M+Na]+	215.766	30932474
AllCCS	[M+H]+	208.8	32859911
AllCCS	[M+H-H2O]+	206.7	32859911
AllCCS	[M+NH4]+	210.6	32859911
AllCCS	[M+Na]+	211.2	32859911
AllCCS	[M-H]-	205.3	32859911
AllCCS	[M+Na-2H]-	207.5	32859911
AllCCS	[M+HCOO]-	210.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.87 minutes	32390414
Predicted by Siyang on May 30, 2022	27.6766 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3766.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	857.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	325.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	340.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	712.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1257.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1125.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2225.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	751.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2159.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	785.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	607.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	279.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	724.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Stigmasterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C	2595.3	Standard polar	33892256
Stigmasterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C	3304.4	Standard non polar	33892256
Stigmasterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C	3316.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Stigmasterol,1TMS,isomer #1	CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3323.8	Semi standard non polar	33892256
Stigmasterol,1TBDMS,isomer #1	CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3554.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	11.15 (0.24-55.00) uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Blood	Detected and Quantified	5.573 +/- 0.727 uM	Adult (>18 years old)	Not Specified	Normal	7595097	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.00003 +/- 0.00003 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17613052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	46.8 +/- 1.2 uM	Adult (>18 years old)	Both	Phytosterolemia	7595097	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Sitosterolemia
Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [PubMed:7595097 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

210250 (Sitosterolemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Stigmasterol

METLIN ID

168

PubChem Compound

5280794

PDB ID

Not Available

ChEBI ID

28824

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Geng, Jianguo; Gu, Wenying; Wang, Xiaobao; Gu, Wenying. Method for extraction stigmasterol from mixed sterol of plant. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 6 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [PubMed:10517218 ]
Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. [PubMed:15893885 ]
Noblet JA, Young DL, Zeng EY, Ensari S: Use of fecal steroids to infer the sources of fecal indicator bacteria in the Lower Santa Ana River Watershed, California: sewage is unlikely a significant source. Environ Sci Technol. 2004 Nov 15;38(22):6002-8. [PubMed:15573599 ]
Triana J, Lopez M, Perez FJ, Gonzalez-Platas J, Quintana J, Estevez F, Leon F, Bermejo J: Sesquiterpenoids from Pulicaria canariensis and their cytotoxic activities. J Nat Prod. 2005 Apr;68(4):523-31. [PubMed:15844941 ]
Valsta LM, Lemstrom A, Ovaskainen ML, Lampi AM, Toivo J, Korhonen T, Piironen V: Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake. Br J Nutr. 2004 Oct;92(4):671-8. [PubMed:15522137 ]
Miettinen TA: Phytosterolaemia, xanthomatosis and premature atherosclerotic arterial disease: a case with high plant sterol absorption, impaired sterol elimination and low cholesterol synthesis. Eur J Clin Invest. 1980 Feb;10(1):27-35. [PubMed:6768564 ]
Urech K, Scher JM, Hostanska K, Becker H: Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L. J Pharm Pharmacol. 2005 Jan;57(1):101-9. [PubMed:15638998 ]
Morin RJ, Elms NJ: Rapid microanalysis of cholesterol in bile and serum by gas chromatography. Ann Clin Lab Sci. 1975 Jan-Feb;5(1):52-6. [PubMed:1111441 ]

Enzymes

Enzyme Details

1. Delta(24)-sterol reductase

General function:: Energy production and conversion
Specific function:: Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:: DHCR24
Uniprot ID:: Q15392
Molecular weight:: 60100.805

Showing metabocard for Stigmasterol (HMDB0000937)

MOL for HMDB0000937 (Stigmasterol)

3D MOL for HMDB0000937 (Stigmasterol)

3D SDF for HMDB0000937 (Stigmasterol)

3D-SDF for HMDB0000937 (Stigmasterol)

PDB for HMDB0000937 (Stigmasterol)

3D PDB for HMDB0000937 (Stigmasterol)

SMILES for HMDB0000937 (Stigmasterol)

INCHI for HMDB0000937 (Stigmasterol)

Structure for HMDB0000937 (Stigmasterol)

3D Structure for HMDB0000937 (Stigmasterol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes