| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2008-08-13 13:47:51 UTC |
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| Update Date | 2020-06-26 16:37:26 UTC |
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| HMDB ID | HMDB0006851 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | delta7-Avenasterol |
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| Description | delta7-Avenasterol, also known as 7-dehydroavenasterol or 24Z-ethylidenelathosterol, 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, delta7-avenasterol is considered to be a sterol lipid molecule. delta7-Avenasterol has been detected, but not quantified in, several different foods, such as garden onions, fenugreeks, vaccinium (blueberry, cranberry, huckleberry), grapefruit/pummelo hybrids, and pulses. This could make delta7-avenasterol a potential biomarker for the consumption of these foods. delta7-Avenasterol is an intermediate in the biosynthesis of steroids. It is the fourth to last step in the synthesis of stigmasterol and is converted from 24-ethylidenelophenol. It is then converted into 5-dehydroavenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 7-Dehydroavenasterol | KEGG | | Δ7-Avenasterol | Generator | | (24Z)-24-Ethyl-5alpha-cholesta-7,24(28)-dien-3beta-ol | HMDB | | (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol | HMDB | | (Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol | HMDB | | 24Z-Ethylidenelathosterol | HMDB | | 3beta-Hydroxy-5alpha-stigmasta-7,24(28)Z-diene | HMDB | | 5alpha-Stigmasta-7,24(28)-dien-3-ol | HMDB | | 5alpha-Stigmasta-7,24(28)-dien-3beta-ol | HMDB | | 5alpha-Stigmasta-7,Z-24(28)-diene-3.beta-ol | HMDB | | Avenasterol | HMDB | | Z-24-Ethylidene-5alpha-cholest-7-en-3beta-ol | HMDB | | (24Z)-24-Ethyl-5α-cholesta-7,24(28)-dien-3β-ol | HMDB | | (24Z)-5α-Stigmasta-7,24(28)-dien-3β-ol | HMDB | | (3beta,5alpha,24Z)-Stigmasta-7,24(28)-dien-3-ol | HMDB | | (3β,5α,24Z)-Stigmasta-7,24(28)-dien-3-ol | HMDB | | (Z)-5α-Stigmasta-7,24(28)-dien-3β-ol | HMDB | | 3β-Hydroxy-5α-stigmasta-7,24(28)Z-diene | HMDB | | 5alpha-Stigmasta-7,Z-24(28)-diene-3beta-ol | HMDB | | 5α-Stigmasta-7,24(28)-dien-3-ol | HMDB | | 5α-Stigmasta-7,Z-24(28)-diene-3β-ol | HMDB | | Z-24-Ethylidene-5α-cholest-7-en-3β-ol | HMDB | | delta7-Avenasterol | HMDB |
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| Chemical Formula | C29H48O |
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| Average Molecular Weight | 412.702 |
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| Monoisotopic Molecular Weight | 412.370516166 |
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| IUPAC Name | (1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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| Traditional Name | (1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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| CAS Registry Number | 23290-26-8 |
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| SMILES | [H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C |
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| 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/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22+,23+,25-,26+,27+,28+,29-/m1/s1 |
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| InChI Key | MCWVPSBQQXUCTB-OQTIOYDCSA-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 | - Triterpenoid
- Stigmastane-skeleton
- 3-beta-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-7-steroid
- Delta-7-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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| Disposition | Route of exposure: Biological location: Source: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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| Physical Properties |
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| State | Solid |
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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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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f7k-1019000000-bccf5d01490277f0f41c | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-06di-2104900000-4f71a97ae7d9183e13f1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ot-1019500000-d9db27d1f0676bf07012 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-4149100000-10c29ad26226f06b5125 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-6197000000-0dad9f7452e27e74d08d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0002900000-322cae85ce921a9ef9e2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0005900000-7f1c49cc0c1fb7a57fb4 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000t-2019000000-1b7f3a8af79353d7fab5 | Spectrum |
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