Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:49:33 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 | [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 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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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
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Biological location
Source
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DarkChem | [M+H]+ | 199.986 | 31661259 | DarkChem | [M-H]- | 199.881 | 31661259 | DeepCCS | [M-2H]- | 246.972 | 30932474 | DeepCCS | [M+Na]+ | 221.042 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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