You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

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

2021-09-14 15:19:06 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 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
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
  9  3  1  1  0  0  0
 11 17  2  0  0  0  0
 12  2  1  1  0  0  0
 18 16  1  0  0  0  0
 15  4  1  6  0  0  0
 16  5  1  1  0  0  0
 15 12  1  0  0  0  0
 19 20  1  0  0  0  0
 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


  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
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
  9  3  1  1  0  0  0
 11 17  2  0  0  0  0
 12  2  1  1  0  0  0
 18 16  1  0  0  0  0
 15  4  1  6  0  0  0
 16  5  1  1  0  0  0
 15 12  1  0  0  0  0
 19 20  1  0  0  0  0
 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

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:77})
 78 81  0  0  0  0  0  0  0  0999 V2000
   -1.7935   -0.4637   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -0.2397   -0.8137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8909    1.2692   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309    1.8440   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.8563   -0.6531 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6062    1.0261   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394    0.8196    0.0313 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.6019    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    2.1671   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    2.0690    0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042    0.9487    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207    0.9741    0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402    0.2707   -0.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9683    0.8405   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2585    0.1813    0.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -1.1356   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.0442   -0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0476   -0.3723   -0.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9027   -1.2648    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710   -0.2789   -0.6455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7940   -0.0009   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874   -1.6428   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581   -1.5838   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -0.5049   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1440   -0.7798    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6195   -1.0787    0.0313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4832   -0.8361    1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -2.5646   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -0.7773   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -0.2983    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3037    0.0032    0.1002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4400   -0.2395   -0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2644   -0.8358    0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0564   -2.3190    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5933    1.4890    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5771    2.3286   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0052    1.8129   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    1.7656   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    1.4023    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    2.8446   -0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795    1.8513    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738    2.4183   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    2.9410    0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.9696    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443    2.0064    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529    0.4522    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6593    1.0378    0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0981   -1.6592   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -1.6837    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.4544   -1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801   -2.0461   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8440   -1.2805    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139   -0.8722    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472   -2.2775    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5702   -2.3525   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495   -1.9858    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823   -1.2861   -2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -2.5582   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -0.8654    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146    0.0404    1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656   -1.7102    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664   -2.8072   -1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031   -2.7825    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0144   -3.1622    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.9564   -1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626   -0.1191    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0694   -0.6567    2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2919   -0.5561    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1566   -2.4815   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0600   -2.6220    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8043   -2.9101    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5174    1.7186    1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7834    3.3871   -0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5712    2.0979   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6530    2.0991   -1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7348    1.2971    0.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1726    2.8883   -0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1140    1.4839   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4  5  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 24  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 10 11  2  0  0  0  0
 10 44  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 47  1  0  0  0  0
 16 17  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 17 18  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 24  1  0  0  0  0
 23 57  1  0  0  0  0
 23 58  1  0  0  0  0
 24 25  1  1  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 25 61  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 28 64  1  0  0  0  0
 29 30  2  0  0  0  0
 29 65  1  0  0  0  0
 30 31  1  0  0  0  0
 30 66  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 31 35  1  0  0  0  0
 33 34  1  0  0  0  0
 33 67  1  0  0  0  0
 33 68  1  0  0  0  0
 34 69  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 72  1  0  0  0  0
 36 73  1  0  0  0  0
 36 74  1  0  0  0  0
 36 75  1  0  0  0  0
 37 76  1  0  0  0  0
 37 77  1  0  0  0  0
 37 78  1  0  0  0  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    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -1.794  -0.464  -1.872  1.00  0.00           H  
HETATM    2  C   UNL     1      -1.659  -0.240  -0.814  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.891   1.269  -0.551  1.00  0.00           C  
HETATM    4  C   UNL     1      -0.531   1.844  -0.069  1.00  0.00           C  
HETATM    5  C   UNL     1       0.485   0.856  -0.653  1.00  0.00           C  
HETATM    6  H   UNL     1       0.606   1.026  -1.723  1.00  0.00           H  
HETATM    7  C   UNL     1       1.839   0.820   0.031  1.00  0.00           C  
HETATM    8  H   UNL     1       1.720   0.602   1.093  1.00  0.00           H  
HETATM    9  C   UNL     1       2.545   2.167  -0.157  1.00  0.00           C  
HETATM   10  C   UNL     1       3.946   2.069   0.374  1.00  0.00           C  
HETATM   11  C   UNL     1       4.604   0.949   0.431  1.00  0.00           C  
HETATM   12  C   UNL     1       6.021   0.974   0.981  1.00  0.00           C  
HETATM   13  C   UNL     1       6.940   0.271  -0.022  1.00  0.00           C  
HETATM   14  H   UNL     1       6.968   0.841  -0.951  1.00  0.00           H  
HETATM   15  O   UNL     1       8.258   0.181   0.522  1.00  0.00           O  
HETATM   16  C   UNL     1       6.408  -1.136  -0.303  1.00  0.00           C  
HETATM   17  C   UNL     1       5.034  -1.044  -0.970  1.00  0.00           C  
HETATM   18  C   UNL     1       4.048  -0.372  -0.010  1.00  0.00           C  
HETATM   19  C   UNL     1       3.903  -1.265   1.224  1.00  0.00           C  
HETATM   20  C   UNL     1       2.671  -0.279  -0.645  1.00  0.00           C  
HETATM   21  H   UNL     1       2.794  -0.001  -1.692  1.00  0.00           H  
HETATM   22  C   UNL     1       1.987  -1.643  -0.599  1.00  0.00           C  
HETATM   23  C   UNL     1       0.558  -1.584  -1.159  1.00  0.00           C  
HETATM   24  C   UNL     1      -0.216  -0.505  -0.397  1.00  0.00           C  
HETATM   25  C   UNL     1      -0.144  -0.780   1.107  1.00  0.00           C  
HETATM   26  C   UNL     1      -2.619  -1.079   0.031  1.00  0.00           C  
HETATM   27  H   UNL     1      -2.483  -0.836   1.085  1.00  0.00           H  
HETATM   28  C   UNL     1      -2.330  -2.565  -0.191  1.00  0.00           C  
HETATM   29  C   UNL     1      -4.039  -0.777  -0.374  1.00  0.00           C  
HETATM   30  C   UNL     1      -4.884  -0.298   0.505  1.00  0.00           C  
HETATM   31  C   UNL     1      -6.304   0.003   0.100  1.00  0.00           C  
HETATM   32  H   UNL     1      -6.440  -0.239  -0.954  1.00  0.00           H  
HETATM   33  C   UNL     1      -7.264  -0.836   0.945  1.00  0.00           C  
HETATM   34  C   UNL     1      -7.056  -2.319   0.632  1.00  0.00           C  
HETATM   35  C   UNL     1      -6.593   1.489   0.323  1.00  0.00           C  
HETATM   36  C   UNL     1      -5.577   2.329  -0.454  1.00  0.00           C  
HETATM   37  C   UNL     1      -8.005   1.813  -0.170  1.00  0.00           C  
HETATM   38  H   UNL     1      -2.202   1.766  -1.470  1.00  0.00           H  
HETATM   39  H   UNL     1      -2.648   1.402   0.222  1.00  0.00           H  
HETATM   40  H   UNL     1      -0.371   2.845  -0.470  1.00  0.00           H  
HETATM   41  H   UNL     1      -0.479   1.851   1.020  1.00  0.00           H  
HETATM   42  H   UNL     1       2.574   2.418  -1.217  1.00  0.00           H  
HETATM   43  H   UNL     1       2.003   2.941   0.387  1.00  0.00           H  
HETATM   44  H   UNL     1       4.429   2.970   0.723  1.00  0.00           H  
HETATM   45  H   UNL     1       6.344   2.006   1.114  1.00  0.00           H  
HETATM   46  H   UNL     1       6.053   0.452   1.937  1.00  0.00           H  
HETATM   47  H   UNL     1       8.659   1.038   0.725  1.00  0.00           H  
HETATM   48  H   UNL     1       7.098  -1.659  -0.964  1.00  0.00           H  
HETATM   49  H   UNL     1       6.320  -1.684   0.635  1.00  0.00           H  
HETATM   50  H   UNL     1       5.112  -0.454  -1.883  1.00  0.00           H  
HETATM   51  H   UNL     1       4.680  -2.046  -1.212  1.00  0.00           H  
HETATM   52  H   UNL     1       4.844  -1.280   1.774  1.00  0.00           H  
HETATM   53  H   UNL     1       3.114  -0.872   1.866  1.00  0.00           H  
HETATM   54  H   UNL     1       3.647  -2.277   0.913  1.00  0.00           H  
HETATM   55  H   UNL     1       2.570  -2.353  -1.186  1.00  0.00           H  
HETATM   56  H   UNL     1       1.950  -1.986   0.435  1.00  0.00           H  
HETATM   57  H   UNL     1       0.582  -1.286  -2.208  1.00  0.00           H  
HETATM   58  H   UNL     1       0.080  -2.558  -1.060  1.00  0.00           H  
HETATM   59  H   UNL     1       0.899  -0.865   1.411  1.00  0.00           H  
HETATM   60  H   UNL     1      -0.615   0.040   1.649  1.00  0.00           H  
HETATM   61  H   UNL     1      -0.666  -1.710   1.331  1.00  0.00           H  
HETATM   62  H   UNL     1      -2.466  -2.807  -1.245  1.00  0.00           H  
HETATM   63  H   UNL     1      -1.303  -2.783   0.102  1.00  0.00           H  
HETATM   64  H   UNL     1      -3.014  -3.162   0.411  1.00  0.00           H  
HETATM   65  H   UNL     1      -4.361  -0.956  -1.389  1.00  0.00           H  
HETATM   66  H   UNL     1      -4.563  -0.119   1.521  1.00  0.00           H  
HETATM   67  H   UNL     1      -7.069  -0.657   2.002  1.00  0.00           H  
HETATM   68  H   UNL     1      -8.292  -0.556   0.713  1.00  0.00           H  
HETATM   69  H   UNL     1      -7.157  -2.482  -0.441  1.00  0.00           H  
HETATM   70  H   UNL     1      -6.060  -2.622   0.954  1.00  0.00           H  
HETATM   71  H   UNL     1      -7.804  -2.910   1.161  1.00  0.00           H  
HETATM   72  H   UNL     1      -6.517   1.719   1.386  1.00  0.00           H  
HETATM   73  H   UNL     1      -5.783   3.387  -0.295  1.00  0.00           H  
HETATM   74  H   UNL     1      -4.571   2.098  -0.103  1.00  0.00           H  
HETATM   75  H   UNL     1      -5.653   2.099  -1.517  1.00  0.00           H  
HETATM   76  H   UNL     1      -8.735   1.297   0.455  1.00  0.00           H  
HETATM   77  H   UNL     1      -8.173   2.888  -0.111  1.00  0.00           H  
HETATM   78  H   UNL     1      -8.114   1.484  -1.203  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3   24   26                                       
CONECT    3    2    4   38   39                                       
CONECT    4    3    5   40   41                                       
CONECT    5    4    6    7   24                                       
CONECT    6    5                                                      
CONECT    7    5    8    9   20                                       
CONECT    8    7                                                      
CONECT    9    7   10   42   43                                       
CONECT   10    9   11   11   44                                       
CONECT   11   10   10   12   18                                       
CONECT   12   11   13   45   46                                       
CONECT   13   12   14   15   16                                       
CONECT   14   13                                                      
CONECT   15   13   47                                                 
CONECT   16   13   17   48   49                                       
CONECT   17   16   18   50   51                                       
CONECT   18   17   11   19   20                                       
CONECT   19   18   52   53   54                                       
CONECT   20   18    7   21   22                                       
CONECT   21   20                                                      
CONECT   22   20   23   55   56                                       
CONECT   23   22   24   57   58                                       
CONECT   24   23    2    5   25                                       
CONECT   25   24   59   60   61                                       
CONECT   26    2   27   28   29                                       
CONECT   27   26                                                      
CONECT   28   26   62   63   64                                       
CONECT   29   26   30   30   65                                       
CONECT   30   29   29   31   66                                       
CONECT   31   30   32   33   35                                       
CONECT   32   31                                                      
CONECT   33   31   34   67   68                                       
CONECT   34   33   69   70   71                                       
CONECT   35   31   36   37   72                                       
CONECT   36   35   73   74   75                                       
CONECT   37   35   76   77   78                                       
CONECT   38    3                                                      
CONECT   39    3                                                      
CONECT   40    4                                                      
CONECT   41    4                                                      
CONECT   42    9                                                      
CONECT   43    9                                                      
CONECT   44   10                                                      
CONECT   45   12                                                      
CONECT   46   12                                                      
CONECT   47   15                                                      
CONECT   48   16                                                      
CONECT   49   16                                                      
CONECT   50   17                                                      
CONECT   51   17                                                      
CONECT   52   19                                                      
CONECT   53   19                                                      
CONECT   54   19                                                      
CONECT   55   22                                                      
CONECT   56   22                                                      
CONECT   57   23                                                      
CONECT   58   23                                                      
CONECT   59   25                                                      
CONECT   60   25                                                      
CONECT   61   25                                                      
CONECT   62   28                                                      
CONECT   63   28                                                      
CONECT   64   28                                                      
CONECT   65   29                                                      
CONECT   66   30                                                      
CONECT   67   33                                                      
CONECT   68   33                                                      
CONECT   69   34                                                      
CONECT   70   34                                                      
CONECT   71   34                                                      
CONECT   72   35                                                      
CONECT   73   36                                                      
CONECT   74   36                                                      
CONECT   75   36                                                      
CONECT   76   37                                                      
CONECT   77   37                                                      
CONECT   78   37                                                      
MASTER        0    0    0    0    0    0    0    0   78    0   78    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:77})
 78 81  0  0  0  0  0  0  0  0999 V2000
   -1.7935   -0.4637   -1.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -0.2397   -0.8137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8909    1.2692   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309    1.8440   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.8563   -0.6531 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6062    1.0261   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394    0.8196    0.0313 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196    0.6019    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    2.1671   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459    2.0690    0.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042    0.9487    0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207    0.9741    0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402    0.2707   -0.0221 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9683    0.8405   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2585    0.1813    0.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079   -1.1356   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -1.0442   -0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0476   -0.3723   -0.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9027   -1.2648    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710   -0.2789   -0.6455 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7940   -0.0009   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9874   -1.6428   -0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581   -1.5838   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157   -0.5049   -0.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1440   -0.7798    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6195   -1.0787    0.0313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4832   -0.8361    1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -2.5646   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -0.7773   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -0.2983    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3037    0.0032    0.1002 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4400   -0.2395   -0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2644   -0.8358    0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0564   -2.3190    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5933    1.4890    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5771    2.3286   -0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0052    1.8129   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    1.7656   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    1.4023    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    2.8446   -0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795    1.8513    1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738    2.4183   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    2.9410    0.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.9696    0.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443    2.0064    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0529    0.4522    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6593    1.0378    0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0981   -1.6592   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198   -1.6837    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.4544   -1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801   -2.0461   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8440   -1.2805    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139   -0.8722    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472   -2.2775    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5702   -2.3525   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495   -1.9858    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5823   -1.2861   -2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -2.5582   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -0.8654    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6146    0.0404    1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656   -1.7102    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664   -2.8072   -1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031   -2.7825    0.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0144   -3.1622    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.9564   -1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5626   -0.1191    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0694   -0.6567    2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2919   -0.5561    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1566   -2.4815   -0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0600   -2.6220    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8043   -2.9101    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5174    1.7186    1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7834    3.3871   -0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5712    2.0979   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6530    2.0991   -1.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7348    1.2971    0.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1726    2.8883   -0.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1140    1.4839   -1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4  5  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 24  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 10 11  2  0  0  0  0
 10 44  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 47  1  0  0  0  0
 16 17  1  0  0  0  0
 16 48  1  0  0  0  0
 16 49  1  0  0  0  0
 17 18  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 24  1  0  0  0  0
 23 57  1  0  0  0  0
 23 58  1  0  0  0  0
 24 25  1  1  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 25 61  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 28 64  1  0  0  0  0
 29 30  2  0  0  0  0
 29 65  1  0  0  0  0
 30 31  1  0  0  0  0
 30 66  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 31 35  1  0  0  0  0
 33 34  1  0  0  0  0
 33 67  1  0  0  0  0
 33 68  1  0  0  0  0
 34 69  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 72  1  0  0  0  0
 36 73  1  0  0  0  0
 36 74  1  0  0  0  0
 36 75  1  0  0  0  0
 37 76  1  0  0  0  0
 37 77  1  0  0  0  0
 37 78  1  0  0  0  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

Physiological effect

Health effect:

Health condition:

Sitosterolemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

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

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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	199.574	31661259
DarkChem	[M-H]-	Predicted	Not Available	199.955	31661259
AllCCS	[M+H]+	Predicted	Not Available	208.771	32859911
AllCCS	[M-H]-	Predicted	Not Available	205.341	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Stigmasterol,1TMS,#1	3323.7876	https://arxiv.org/abs/1905.12712
Stigmasterol,1TBDMS,#1	3554.5486	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-3941000000-4b20188a87c1dadeae49	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-9720000000-02211a4df6ec5c313295	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053r-7941000000-7983b2cb8a74cfda7530	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-9731000000-168578ccead65322e450	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-3941000000-4b20188a87c1dadeae49	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-9720000000-02211a4df6ec5c313295	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053r-7941000000-7983b2cb8a74cfda7530	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a59-9731000000-168578ccead65322e450	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-1109000000-be897608aaeab74e5d13	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0avl-2102900000-564b610342ad160ee822	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a59-8920000000-c7d02c3957677fae28be	2015-03-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-24fa3ff739ff064312ab	2021-09-18	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-8900000000-5b42adf83e422cffefb6	2021-09-18	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03di-0000900000-f7738a3fcdee344f82c9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-07cs-9400200000-959314bea26c5acd8301	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a59-7900000000-ce066e558ecbe29afea8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0a4i-3941000000-f854893a9352ff766734	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a59-9720000000-5a3d902c3cd2af078da3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-053r-7941000000-6c5c63e8c487f86b353b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a59-9731000000-32a70fa14fd448314caa	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2019500000-3495ed3a1955cc77528a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9128100000-3c3b91bb2d698a88f9db	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-8197000000-a80e8fcc32cd4a2dfefe	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-322cae85ce921a9ef9e2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0004900000-d25be97b0cfa1b9bed79	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-2019000000-3b119d03e184f575cdc4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03xr-2219400000-9acb072e76ff1b8f2e48	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-7259000000-a7f52c0e28b61ef2a3ac	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9320000000-8a54eac3182f86b7095b	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-363450e12a0ea926276e	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-fe3ab0b12c2d51198ed0	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1001900000-43dce6fa5af31f5d7958	2021-09-07	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)	2015-03-12	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl₃, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	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 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	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	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

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

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 ]
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 ]
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 ]
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 ]
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 ]
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)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes