Obtusifoliol (BioCAD00000015484)

microbial natural products plant natural products marine natural products

Metabolite Card

Chinese Name: 钝叶醇
Formula: C30H50O (426.3861)
SMILES: 

[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C

Synonyms [en]

obtusifoliol; 4alpha,14alpha-dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-ol; 4alpha,14alpha-Dimethyl-24-methylene-5alpha-cholesta-8-en-3beta-ol; (+)-OBTUSIFOLIOL; 4alpha,14alpha-dimethyl-24-methylene-cholest-8-en-3beta-ol; 3RH57E39ER

Reviewed

Last reviewed on 2026-04-16.

Cite this Page

Obtusifoliol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/Obtusifoliol (retrieved 2026-08-21) (CAD Registry RN: BioCAD00000015484). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Obtusifoliol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 14250-23-8
  • CAS Registry Number: 16910-32-0
  • CAS Registry Number: 65982-33-4
  • PubChem: 390622
  • PubChem: 634321
  • PubChem: 65252
  • ChEBI: ChEBI:17791
  • HMDB: HMDB0001242
  • LipidMaps: LMST01030101
  • KEGG: C01943
  • BioCyc: OBTUSIFOLIOL
  • NCBI MeSH: obtusifoliol
  • Wikipedia: Obtusifoliol
  • MoNA: HMDB0001242_c_ms_102651
  • Metlin: METLIN_41730
  • Coconut NaturalProduct: CNP0112564.1
  • Coconut NaturalProduct: CNP0179802.2
  • Coconut NaturalProduct: CNP0179802.4
  • Coconut NaturalProduct: CNP0179802.5
  • Coconut NaturalProduct: CNP0534508.0
  • PMHub: MS000017403
  • metaboanalyst: 1db68795738c9ad1b48b119600ecd4b1
  • metaboanalyst: 4e2e6db3ed5272ec9d1f3a174efea9b8
  • metaboanalyst: 6b3e53203899083a3f1b4a35936a8982
  • HERB: HBIN037672

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03775 5.5.1.9 cycloeucalenol lyase (cyclopropane-decyclizing)
KEGG:R05731 1.14.14.154 obtusifoliol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (14-methyl cleaving)
Rhea:RHEA:14918 1.14.14.154 obtusifoliol + 3 reduced [NADPH—hemoprotein reductase] + 3 O2 => 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+
Rhea:RHEA:14919 1.14.14.154 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+ => obtusifoliol + 3 reduced [NADPH—hemoprotein reductase] + 3 O2
Rhea:RHEA:14920 1.14.14.154 obtusifoliol + 3 reduced [NADPH—hemoprotein reductase] + 3 O2 <=> 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 3 oxidized [NADPH—hemoprotein reductase] + 4 H2O + 4 H+
Rhea:RHEA:22801 5.5.1.9 cycloeucalenol => obtusifoliol
Rhea:RHEA:22802 5.5.1.9 obtusifoliol => cycloeucalenol
Rhea:RHEA:22803 5.5.1.9 cycloeucalenol <=> obtusifoliol
Rhea:RHEA:56757 obtusifoliol + 6 reduced [2Fe-2S]-[ferredoxin] + 3 O2 + 5 H+ => 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 6 oxidized [2Fe-2S]-[ferredoxin] + 4 H2O
Rhea:RHEA:56758 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 6 oxidized [2Fe-2S]-[ferredoxin] + 4 H2O => obtusifoliol + 6 reduced [2Fe-2S]-[ferredoxin] + 3 O2 + 5 H+
Rhea:RHEA:56759 obtusifoliol + 6 reduced [2Fe-2S]-[ferredoxin] + 3 O2 + 5 H+ <=> 4α-methyl-5α-ergosta-8,14,24(28)-trien-3β-ol + formate + 6 oxidized [2Fe-2S]-[ferredoxin] + 4 H2O
BioCyc:1.14.13.70-RXN 1.14.14.154 OBTUSIFOLIOL + 3 OXYGEN-MOLECULE + 3 Red-NADPH-Hemoprotein-Reductases --> ALPHA-METHYL-5-ALPHA-ERGOSTA + FORMATE + 4 WATER + 3 Ox-NADPH-Hemoprotein-Reductases + PROTON
BioCyc:CYCLOEUCALENOL-CYCLOISOMERASE-RXN 5.5.1.9 CYCLOEUCALENOL --> OBTUSIFOLIOL
BioCyc:RXN-19831 OBTUSIFOLIOL + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-21438 + WATER + Ox-NADPH-Hemoprotein-Reductases
BioCyc:RXN-13896 2.1.1.- S-ADENOSYLMETHIONINE + OBTUSIFOLIOL --> CPD-14905 + ADENOSYL-HOMO-CYS + PROTON
Rhea:RHEA:14917 [14917] obtusifoliol + 3 reduced [NADPH--hemoprotein reductase] + 3 O2 = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 3 oxidized [NADPH--hemoprotein reductase] + 4 H2O + 4 H(+)
Rhea:RHEA:22800 [22800] cycloeucalenol = obtusifoliol
Rhea:RHEA:56756 [56756] obtusifoliol + 6 reduced [2Fe-2S]-[ferredoxin] + 3 O2 + 5 H(+) = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 6 oxidized [2Fe-2S]-[ferredoxin] + 4 H2O
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Mass Spectrum
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View All Mass Spectrum
Organism Source

Taxonomy Source

  1. Cordyceps sinensis [ncbi taxid: ]
  2. Sphaeria macula [ncbi taxid: ]
  3. Ageratina riparia [ncbi taxid: 287013]
  4. Arabidopsis thaliana [ncbi taxid: 3702]
  5. Aristolochia tagala [ncbi taxid: 158573]
  6. Asparagus thunbergianus [ncbi taxid: ]
  7. Aspergillus wentii [ncbi taxid: 5066]
  8. Astragalus interpositus [ncbi taxid: ]
  9. Botryotrichum piluliferum [ncbi taxid: 155880]
  10. Caesalpinia pulcherrima [ncbi taxid: 53846]
  11. Calea clausseniana [ncbi taxid: ]
  12. Camellia reticulata [ncbi taxid: 452972]
  13. Candida albicans [ncbi taxid: 5476]
  14. Capsicum annuum [ncbi taxid: 4072]
  15. Chalciporus piperatus [ncbi taxid: 145387]
  16. Chromodoris inornata [ncbi taxid: ]
  17. Chromodoris willani [ncbi taxid: 508140]
  18. Coleostephus myconis [ncbi taxid: 99042]
  19. Conus marmoreus [ncbi taxid: 42752]
  20. Corylus avellana [ncbi taxid: 13451]
  21. Corylus maxima [ncbi taxid: 126985]
  22. Cylicodaphne sebifera [ncbi taxid: ]
  23. Dactylosporangium aurantiacum [ncbi taxid: 35754]
  24. Dahlia pinnata [ncbi taxid: 101596]
  25. Datura metel [ncbi taxid: 35625]
  26. Dolichothele uberiformis [ncbi taxid: ]
  27. Dryopteris sacrosancta [ncbi taxid: 239594]
  28. Eleusine indica [ncbi taxid: 29674]
  29. Euphorbia chamaesyce [ncbi taxid: 1046441]
  30. Euphorbia guyoniana [ncbi taxid: 1138347]
  31. Euphorbia officinarum [ncbi taxid: 1130835]
  32. Euphorbia peplus [ncbi taxid: 38846]
  33. Glycine max [ncbi taxid: 3847]
  34. Gynostemma pentaphyllum [ncbi taxid: 182084]
  35. Heimia salicifolia [ncbi taxid: 312921]
  36. Hippophae rhamnoides [ncbi taxid: 193516]
  37. Jungermannia subulata [ncbi taxid: ]
  38. Justicia simplex [ncbi taxid: ]
  39. Lemna trisulca [ncbi taxid: 161105]
  40. Leptoshaeria maculans [ncbi taxid: ]
  41. Libocedrus yateensis [ncbi taxid: 103975]
  42. Lotus albus [ncbi taxid: ]
  43. Lycium chinense [ncbi taxid: 112883]
  44. Lycopersicon esculentum [ncbi taxid: ]
  45. Microlepia speluncae [ncbi taxid: 449865]
  46. Monilinia fructigena [ncbi taxid: 38457]
  47. Mucor pusillus [ncbi taxid: ]
  48. Mycena haematopus [ncbi taxid: 230807]
  49. Mycobacterium avium subsp. paratuberculosis [ncbi taxid: 1770]
  50. Narcissus asturiensis [ncbi taxid: 54837]
  51. Nicotiana benthamiana [ncbi taxid: 4100]
  52. Niphogeton ternata [ncbi taxid: 681593]
  53. Oenothera biennis [ncbi taxid: 3942]
  54. Papaver commutatum [ncbi taxid: 357467]
  55. Pelargonium hortorum [ncbi taxid: ]
  56. Pertusaria wulfenii [ncbi taxid: ]
  57. Piptadenia peregrina [ncbi taxid: ]
  58. Rhoiptelea chiliantha [ncbi taxid: 60426]
  59. Rubus koehneanus [ncbi taxid: ]
  60. Ruscus hypophyllum [ncbi taxid: 1142958]
  61. Saccharomyces cerevisiae [ncbi taxid: 4932]
  62. Scutellaria orientalis [ncbi taxid: 53170]
  63. Sideritis discolor [ncbi taxid: 403019]
  64. Solanum melongena [ncbi taxid: 4111]
  65. Sphaeria macula [ncbi taxid: ]
  66. Stemphylium radicinum [ncbi taxid: ]
  67. Streptomyces aureus [ncbi taxid: 193461]
  68. Streptomyces ipomoeae [ncbi taxid: 103232]
  69. Synotis alata [ncbi taxid: 308345]
  70. Tripteris vaillantii [ncbi taxid: 1670870]
  71. Ustilago maydis [ncbi taxid: ]
  72. Mus musculus [ncbi taxid: 10090]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-7155 7-dehydroporiferasterol biosynthesis
BioCyc:META_PWY-2541 plant sterol biosynthesis
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