beta-Sitosterol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for beta-Sitosterol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the beta-Sitosterol?

The molecule beta-Sitosterol presents a molecular formula of C29H50O and its IUPAC name is (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol.

Beta-Sitosterol is a plant sterol with a structure similar to cholesterol. It belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

Beta-Sitosterol is an important plant sterol. It is similar in structure to cholesterol and belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

Beta-Sitosterol is a plant sterol with a structure similar to cholesterol. It belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

Beta-Sitosterol is an important plant sterol. It is similar in structure to cholesterol and belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

Beta-Sitosterol is a plant sterol with a structure similar to cholesterol. It belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

Beta-Sitosterol is an important plant sterol. It is similar in structure to cholesterol and belongs in many plants, including saw palmetto and soy. Beta-Sitosterol is used for treating benign prostatic hyperplasia (BPH), high cholesterol, and other conditions..

3D structure

Cartesian coordinates

Geometry of beta-Sitosterol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

beta-Sitosterol KZJWDPNRJALLNS-VJSFXXLFSA-N chemical compound 2D structure molecule svg
beta-Sitosterol

 

Molecule descriptors

 
IUPAC name(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChI codeInChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyKZJWDPNRJALLNS-VJSFXXLFSA-N
SMILESCC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-b-Sitosterol
  • (-)-beta-Sitosterol
  • (24R)-Ethylcholest-5-en-3b-ol
  • (24R)-Ethylcholest-5-en-3beta-ol
  • (24R)-Stigmast-5-en-3b-ol
  • (24R)-Stigmast-5-en-3beta-ol
  • (3-beta)-Stigmast-5-en-3-ol
  • (3.BETA.)-STIGMAST-5-EN-3-OL
  • (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • (3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • (3S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • (3beta)-Stigmast-5-en-3-ol
  • .DELTA.(SUP 5)-STIGMASTEN-3.BETA.-OL
  • .alpha.-Dihydrofucosterol
  • .alpha.-Phytosterol
  • .beta.-Sitosterin
  • .beta.-Sitosterol
  • .beta.Sitosterin
  • .beta.Sitosterol
  • 14-((1S,4R)-4-ethyl-1,5-dimethylhexyl)(1S,5S,10S,11S,2R,14R,15R)-2,15-dimethyl tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
  • 17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • 22,23-Dihydrostigmasterol
  • 22,23-dihydro-Stigmasterol
  • 24-Ethylcholest-5-en-3.beta.-ol
  • 24-alpha-Ethylcholesterol
  • 24.BETA.-ETHYL-.DELTA.(SUP 5)-CHOLESTEN-3.BETA.-OL
  • 24.alpha.-Ethylcholesterol
  • 24a-Ethylcholesterol
  • 24alpha-Ethylcholesterol
  • 76772-70-8
  • 83-46-5
  • A840577
  • AB00513984
  • AC-24183
  • ACon1_000287
  • AI3-26020
  • Angelicin (steroid)
  • Azuprostat
  • B-Sitosterol
  • BDBM50218197
  • BETA-SITOSTEROL
  • BIDD:ER0636
  • BIDD:PXR0121
  • BPBio1_001155
  • BSPBio_001049
  • Beta-sistosterol
  • Betaprost
  • C01753
  • CCG-208334
  • CCRIS 5529
  • Cinchol
  • Cupreol
  • D08518
  • D5-Stigmasten-3b-ol
  • DB14038
  • DSSTox_CID_2481
  • DSSTox_GSID_22481
  • DSSTox_RID_76601
  • Delta5-Stigmasten-3b-ol
  • HMS1571E11
  • HMS2098E11
  • Harzol
  • LMST01040129
  • MEGxp0_001710
  • MFCD00003631
  • N1688
  • NCGC00095716-01
  • NCGC00142598-02
  • NCGC00142598-03
  • NCI60_041777
  • NSC 18173
  • NSC 8096
  • NSC-18173
  • NSC-49083
  • NSC-8096
  • NSC18173
  • NSC49083
  • NSC8096
  • Nimbosterol
  • Phytosterol
  • Prestwick0_000985
  • Prestwick1_000985
  • Prestwick2_000985
  • Prestwick3_000985
  • Prostasal
  • Q-200712
  • Q63409374
  • Quebrachol
  • Rhamnol
  • S0040
  • S347WMO6M4
  • SITOSTEROL, BETA
  • SITOSTEROL, BETA-
  • SKF 14463
  • SMP1_000274
  • SR-05000002307
  • SR-05000002307-2
  • SR-05000002307-3
  • Sito-Lande
  • Sitosterol
  • Sitosterol beta
  • Sitosterol, .beta.
  • Sobatum
  • Steroids, hydroxy
  • Stigmast-5-en-3-beta-ol
  • Stigmast-5-en-3-ol, (3.beta.)-
  • Stigmast-5-en-3-ol, (3b)-
  • Stigmast-5-en-3-ol, (3beta)-
  • Stigmast-5-en-3.beta.-ol
  • Stigmast-5-en-3b-ol
  • Stigmast-5-en-3beta-ol
  • Stigmasterol, 22,23-dihydro-
  • Stigmasterol,23-dihydro-
  • Triastonal
  • a-Dihydrofucosterol
  • a-Phytosterol
  • alpha-Dihydrofucosterol
  • alpha-Phytosterol
  • alpha.Dihydrofucosterol
  • b-Sitosterin
  • beta Sitosterol
  • beta-Phytosterol
  • beta-Sitosterin
  • beta-Sitosterol
  • beta-Sitosterol (Synthetic)
  • delta5-Stigmasten-3-beta-ol
  • s2273
  • sitosterin
  • ss--Sitosterol
  • stigmast-5-ene-3beta-ol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4095717
  • CAS-83-46-5
  • UNII-S347WMO6M4
  • AKOS005267194
  • DTXSID5022481
  • CHEMBL221542
  • CHEBI:27693
  • CHEBI:176889
  • Tox21_111514
  • EINECS 201-480-6
  • SPBio_002950
  • SCHEMBL16105

Physico-Chemical properties

IUPAC name(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Molecular formulaC29H50O
Molecular weight414.707
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity133.23
LogP8.0
Topological polar surface area20.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.