(3S,10S,13R)-10,13-Dimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
PubChem CID: 23724574
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| Compound Synonyms | (3S,10S,13R)-10,13-Dimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, SCHEMBL13324299, CHEBI:80096, Q27149246 |
|---|---|
| Topological Polar Surface Area | 20.2 |
| Hydrogen Bond Donor Count | 1.0 |
| Heavy Atom Count | 30.0 |
| Description | Constituent of oats and pumpkin seeds delta7-Avenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15782). It is the 4th to last step in the synthesis of Stigmasterol and is converted from 24-Ethylidenelophenol. It is then converted to 5-dehydroavenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. delta7-Avenasterol is found in many foods, some of which are robusta coffee, sunflower, oat, and common walnut. |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 686.0 |
| Database Name | fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 4.0 |
| Iupac Name | (3S,10S,13R)-10,13-dimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| Nih Violation | False |
| Class | Steroids and steroid derivatives |
| Xlogp | 8.6 |
| Superclass | Lipids and lipid-like molecules |
| Is Pains | False |
| Subclass | Stigmastanes and derivatives |
| Molecular Formula | C29H48O |
| Inchi Key | MCWVPSBQQXUCTB-RFOHPFAESA-N |
| Rotatable Bond Count | 5.0 |
| State | Solid |
| Synonyms | (24Z)-24-Ethyl-5alpha-cholesta-7,24(28)-dien-3beta-ol, (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol, (Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol, 24Z-Ethylidenelathosterol, 3beta-Hydroxy-5alpha-stigmasta-7,24(28)Z-diene, 5alpha-Stigmasta-7,24(28)-dien-3-ol, 5alpha-Stigmasta-7,24(28)-dien-3beta-ol, 5alpha-Stigmasta-7,Z-24(28)-diene-3.beta-ol, 7-Dehydroavenasterol, Avenasterol, D7-Avenasterol, delta7-Avenasterol, Z-24-Ethylidene-5alpha-cholest-7-en-3beta-ol |
| Substituent Name | Polycyclic triterpenoid, Triterpenoid, Stigmastane-skeleton, 3-beta-hydroxy-delta-7-steroid, 3-beta-hydroxysteroid, Hydroxysteroid, 3-hydroxysteroid, 3-hydroxy-delta-7-steroid, Delta-7-steroid, Cyclic alcohol, Secondary alcohol, Hydrocarbon derivative, Organooxygen compound, Alcohol, Aliphatic homopolycyclic compound |
| Compound Name | (3S,10S,13R)-10,13-Dimethyl-17-[(Z,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| Kingdom | Organic compounds |
| Exact Mass | 412.371 |
| Formal Charge | 0.0 |
| Brenk Violation | True |
| Monoisotopic Mass | 412.371 |
| Hydrogen Bond Acceptor Count | 1.0 |
| Molecular Weight | 412.7 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 8.0 |
| Total Bond Stereocenter Count | 1.0 |
| Inchi | 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 |
| Smiles | C/C=C(/CC[C@@H](C)C1CCC2[C@@]1(CCC3C2=CCC4[C@@]3(CC[C@@H](C4)O)C)C)\C(C)C |
| Defined Bond Stereocenter Count | 1.0 |
- 1. Outgoing r'ship
FOUND_INto/from Avena Sativa (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Coffea Canephora (Plant) Rel Props:Source_db:fooddb_chem_all - 3. Outgoing r'ship
FOUND_INto/from Helianthus Annuus (Plant) Rel Props:Source_db:fooddb_chem_all - 4. Outgoing r'ship
FOUND_INto/from Juglans Regia (Plant) Rel Props:Source_db:fooddb_chem_all - 5. Outgoing r'ship
FOUND_INto/from Lactuca Sativa (Plant) Rel Props:Source_db:fooddb_chem_all - 6. Outgoing r'ship
FOUND_INto/from Moringa Oleifera (Plant) Rel Props:Source_db:fooddb_chem_all