| Record Information |
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| Version | 1.0 |
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| Creation Date | 2018-06-29 22:18:06 UTC |
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| Update Date | 2020-05-11 20:56:43 UTC |
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| BMDB ID | BMDB0062198 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | beta-Sitosterol |
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| Description | beta-Sitosterol, also known as sitosterol or a-phytosterol, 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. Thus, beta-sitosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on beta-Sitosterol. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-beta-Sitosterol | ChEBI | | (24R)-Ethylcholest-5-en-3beta-ol | ChEBI | | (24R)-Stigmast-5-en-3beta-ol | ChEBI | | (3beta)-Stigmast-5-en-3-ol | ChEBI | | 22,23-Dihydrostigmasterol | ChEBI | | 24alpha-Ethylcholesterol | ChEBI | | alpha-Dihydrofucosterol | ChEBI | | Azuprostat | ChEBI | | beta-Sitosterin | ChEBI | | Cupreol | ChEBI | | Nimbosterol | ChEBI | | Triastonal | ChEBI | | Sitosterol | Kegg | | Harzol | Kegg | | (-)-b-Sitosterol | Generator | | (-)-Β-sitosterol | Generator | | (24R)-Ethylcholest-5-en-3b-ol | Generator | | (24R)-Ethylcholest-5-en-3β-ol | Generator | | (24R)-Stigmast-5-en-3b-ol | Generator | | (24R)-Stigmast-5-en-3β-ol | Generator | | (3b)-Stigmast-5-en-3-ol | Generator | | (3Β)-stigmast-5-en-3-ol | Generator | | 24a-Ethylcholesterol | Generator | | 24Α-ethylcholesterol | Generator | | a-Dihydrofucosterol | Generator | | Α-dihydrofucosterol | Generator | | b-Sitosterin | Generator | | Β-sitosterin | Generator | | b-Sitosterol | Generator | | Β-sitosterol | Generator | | 24-Ethylcholest-5-en-3 beta-ol | HMDB | | 24-Ethylcholesterol | HMDB | | 3beta-Sitosterol | HMDB | | 3beta-Stigmast-5-en-3-ol | HMDB | | Clionasterol | HMDB | | Sitosterol, (3beta)-isomer | HMDB | | 22,23-Dihydro-stigmasterol | HMDB | | a-Phytosterol | HMDB | | alpha-Phytosterol | HMDB | | Angelicin | HMDB | | beta-Phytosterol | HMDB | | Cinchol | HMDB | | D5-Stigmasten-3b-ol | HMDB | | Delta5-Stigmasten-3b-ol | HMDB | | Phytosterol | HMDB | | Prostasal | HMDB | | Quebrachol | HMDB | | Rhamnol | HMDB | | Sito-lande | HMDB | | Sobatum | HMDB | | Stigmast-5-en-3-ol | HMDB | | Stigmast-5-en-3b-ol | HMDB | | Stigmast-5-en-3beta-ol | HMDB | | Stigmast-5-en-3β-ol | HMDB | | delta5-Stigmasten-3beta-ol | HMDB | | Δ5-stigmasten-3β-ol | HMDB | | Α-phytosterol | HMDB | | Rhammol | HMDB | | Δ5-stigmasten-3beta-ol | HMDB | | beta-Sitosterol | ChEBI |
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| Chemical Formula | C29H50O |
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| Average Molecular Weight | 414.718 |
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| Monoisotopic Molecular Weight | 414.38616623 |
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| IUPAC Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| Traditional Name | (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol |
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| CAS Registry Number | 83-46-5 |
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| SMILES | [H][C@@](CC)(CC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)C |
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| InChI Identifier | InChI=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 |
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| InChI Key | KZJWDPNRJALLNS-VJSFXXLFSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Stigmastanes and derivatives |
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| Direct Parent | Stigmastanes and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Membrane
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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