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5alpha,8alpha-epidioxy-ergost-6,22-dien-3beta-ol
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi, Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | O[C@H]1CC[C@]2([C@@]3(C1)OO[C@@]1([C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C=C3)C |
|---|---|
| InChI | InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1 |
| InChIKey | VXOZCESVZIRHCJ-KGHQQZOUSA-N |
| Formula | C28H44O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 428.66 |
| Rotatable Bonds | 4 |
| TPSA | 38.69 |
| LogP | 6.47 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 428.33 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Agaricus species | Agaricaceae | Fungi | 5340 |
| 2 | Termitomyces letestui | Lyophyllaceae | Fungi | 2093650 |
| 3 | Lactarius edulis | Russulaceae | Fungi | 1459041 |
| 4 | Ganoderma sp | Ganodermataceae | Plantae | 1869158 |
| 5 | Solanum nigrum | Solanaceae | Plantae | 4112 |
| 6 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
5alpha,8alpha-epidioxy-ergost-6,22-dien-3beta-ol
Ergosterol peroxide
Ergosterol-5,8-peroxide
2061-64-5
Ergosterol endoperoxide
Peroxyergosterol
Ergosterol 5alpha,8alpha-epidioxide
UG9TN81TGH
CHEMBL434750
CHEBI:65858
NSC31324
NSC-31324
(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol
5alpha,8alpha-epidioxy-22E-ergosta-6,22-dien-3beta-ol
(22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol
5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol
(24R)-5alpha,8alpha-epidioxy-24-methylcholesta-6,22-dien-3beta-ol
NSC 31324
(3S,5S,8S,9R,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
UNII-UG9TN81TGH
(3beta,5alpha,8alpha,22E)-5,8-epidioxyergosta-6,22-dien-3-ol
5.alpha.,8.alpha.-Ergosta-6,22-dien-3.beta.-ol, 5,8-epidioxy-
Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-
Ergosterol 5.alpha.,8.alpha.-epidioxide
Ergosterol 5-alpha,8-alpha-epidioxide
BRN 0096852
ERGOSTERYL PEROXIDE
5alpha,8alpha-Ergosta-6,22-dien-3beta-ol, 5,8-epidioxy-
5-19-03-00043 (Beilstein Handbook Reference)
Ergosterol Peroxide_120246
SCHEMBL3281353
ERGOSTEROL 5,8-PEROXIDE
5,8-Epidioxy-5-alpha,8-alpha-ergosta-6,22-dien-3-beta-ol
DTXSID501021533
HY-N3845
BDBM50334064
AKOS040760078
FE42618
DA-63258
CS-0024320
5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTEROL
G12469
5.alpha.,22-dien-3.beta.-ol, 5,8-epidioxy-
5alpha,8alpha-Epidioxyergosta-6,22-diene-3beta-ol
Q5385831
5-alpha,8-alpha-ERGOSTA-6,22-DIEN-3-beta-OL, 5,8-EPIDIOXY-
Ergosta-6, 5,8-epidioxy-, (3.beta.,5.alpha.,8.alpha.,22E)-
(22E)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL
(24R)-ERGOST-5.ALPHA.,8.ALPHA.-EPIDIOXY-6,22-DIEN-3.BETA.-OL
3.BETA.-HYDROXY-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIENE
Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3-beta,5-alpha,8-alpha,22E)-
Ergosta-6,22-dien-3-ol, 5,8-epidioxy-, (3beta,5alpha,8alpha,22E)-
(22E,24R)-5.ALPHA.,8.ALPHA.-EPIDIOXYERGOSTA-6,22-DIEN-3.BETA.-OL
5.ALPHA.,8.ALPHA.-EPIDOXY-(22E,24R)-ERGOSTA-6,22-DIEN-3.BETA.-OL
(1S,2R,5R,6R,9R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadec-18-en-13-ol
- Baraza LD, Joseph CC, et al. (2007). Chemical constituents and biological activity of three Tanzanian wild mushroom species. Tanzanian Journal of Sciences,2007,33,1-7. [View]
- Kojom Foko L.P, Jakhan J, et al. (2024). New antimalarial lanostane triterpenes from a new isolate of Egyptian Ganoderma species. Journal of parasitic diseases : official organ of the Indian Society for Parasitology, 2024, 48(3), 610-623. [View] [PubMed]
- Elsbaey M, Tanaka C, et al. (2019). New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2019,32,70-76. [View]
- El-Hawary S.S, Sayed A.M, et al. (2017). Secondary metabolites from fungal endophytes of Solanum nigrum. Natural product research, 2017, 31(21), 2568-2571. [View] [PubMed]
Pubchem:
5351516
Cas:
2061-64-5
Gnps:
CCMSLIB00000478084
Zinc:
ZINC000038139718
Chebi:
65858
Metabolights:
MTBLC65858
Chembl:
CHEMBL434750
Bindingdb:
50334064
CPRiL:
56301
SMILES: C1CCC(C1C234)CCC3C5C(OO4)(C=C2)CCCC5
Level: 0
Mol. Weight: 428.66 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.62
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.58
- Plasma Protein Binding
- 79.54
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.24
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.13
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.75
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -62.58
- Rat (Acute)
- 3.12
- Rat (Chronic Oral)
- 1.19
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 438.51
- Hydration Free Energy
- -2.91
- Log(D) at pH=7.4
- 5.55
- Log(P)
- 7.57
- Log S
- -6.9
- Log(Vapor Pressure)
- -7.69
- Melting Point
- 151.61
- pKa Acid
- 9.89
- pKa Basic
- 6.67
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8828 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8828 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8740 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8740 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8679 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8679 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8440 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8440 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8327 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8327 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8212 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8212 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.8038 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.8038 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8037 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8037 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7968 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7968 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.7939 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.7939 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7895 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7895 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7859 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7859 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7805 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7805 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7767 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7767 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7562 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7562 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7550 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7550 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7517 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7517 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7470 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7470 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7442 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7442 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7372 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7372 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7333 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7333 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7300 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7300 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7266 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7266 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7214 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7214 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7204 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7204 |