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Ergosterol
- Family: Fungi - Russulaceae
- Kingdom: Fungi
-
Class: Steroid
- Subclass: Sterol
| Canonical Smiles | O[C@H]1CC[C@]2(C(=CC=C3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C1)C |
|---|---|
| InChI | InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1 |
| InChIKey | DNVPQKQSNYMLRS-APGDWVJJSA-N |
| Formula | C28H44O |
| HBA | 1 |
| HBD | 1 |
| MW | 396.66 |
| Rotatable Bonds | 4 |
| TPSA | 20.23 |
| LogP | 7.33 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.79 |
| Exact Mass | 396.34 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus austroafricanus | Eurotiomycetidae | Fungi | 1220192 |
| 2 | Aspergillus flavipes | Trichocomaceae | Fungi | 41900 |
| 3 | Agaricus species | Agaricaceae | Fungi | 5340 |
| 4 | Termitomyces letestui | Lyophyllaceae | Fungi | 2093650 |
| 5 | Lactarius edulis | Russulaceae | Fungi | 1459041 |
Showing of synonyms
Ergosterol
57-87-4
Provitamin D2
Ergosterin
UNII-Z30RAY509F
CCRIS 7220
HSDB 395
Z30RAY509F
CHEBI:16933
24-Methylcholesta-5,7,22-trien-3beta-ol
Ergosta-5,7,22-trien-3beta-ol
EINECS 200-352-7
Ergosta-5,7,22-trien-3-ol, (3beta,22E)-
24alpha-Methyl-22E-dehydrocholesterol
(22E)-ergosta-5,7,22-trien-3beta-ol
(22E,24S)-24-methylcholesta-5,7,22-trien-3beta-ol
AI3-18876
24R-Methylcholesta-5,7,2E-trien-3beta-ol
(3beta,22E)-Ergosta-5,7,22-trien-3-ol
DTXSID90878679
ERGOSTEROL (USP-RS)
ERGOSTEROL [USP-RS]
Provitamin D 2
Pro Vitamin D2
Pro-Vitamin D2
D2, Pro-Vitamin
ERGOCALCIFEROL IMPURITY B (EP IMPURITY)
ERGOCALCIFEROL IMPURITY B [EP IMPURITY]
Ergosta-5:6,7:8,22:23-trien-3-ol
DTXCID201016721
DELTA-5,7,22-ERGOSTATRIEN-3BETA-OL
ERGOSTEROL (CONSTITUENT OF GANODERMA LUCIDUM FRUITING BODY)
200-352-7
Ergosta-5,7,22-trien-3-ol, (3b,22E)-
Ergosta-5,7,22E-trien-3beta-ol
5,7,22-Ergostatrien-3beta-ol
3beta-Hydroxy-5,7,22-ergostatriene
(22E)-Ergosta-5,7,22-trien-3.beta.-ol
Ergosterol (Provitamin D2)
(3.beta.,22E)-Ergosta-5,7,22-trien-3-ol
Ergosta-5,7,22-trien-3-ol, (3.beta.,22E)-
MFCD00003623
Ergosta-5,7,22-trien-3-ol
NSC62791
Provitamine D2
(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(E,1R,4R)-1,4,5-trimethylhex-2-enyl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Ergosterol, >=75%
ERGOSTEROL [MI]
ERGOSTEROL [HSDB]
Bmse000494
SCHEMBL43194
(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
MEGxm0_000450
CHEMBL1232562
ACon0_000429
ACon1_000637
24a-Methyl-22E-dehydrocholesterol
Ergosterol, >=95.0% (HPLC)
HY-N0181
BDBM50378884
LMST01030093
S2297
24alpha-Methyl-22E-dehydrocholestero
AKOS015918128
AC-8370
DB04038
DS-4956
FE30866
(24R)-Ergosta-5,7,22-trien-3b-ol
(3beta)-Ergosta-5,7,22-trien-3-ol
NCGC00168889-01
NCGC00168889-02
(3S,9S,10R,13R,14R,17R)-17-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
14-((2E)(1R,4R)-1,4,5-trimethylhex-2-enyl)(1S,5S,2R,11R,14R,15R)-2,15-dimethyl tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadeca-7,9-dien-5-ol
24-Methylcholesta-5,7,22-trien-3b-ol
BP-40655
24R-Methylcholesta-5,7,22E-trien-3b-ol
(3beta,2E)-Ergosta-5,7,22-trien-3-ol
CS-0007890
NS00008818
24R-Methylcholesta-5,7,22E-trien-3beta-ol
C01694
EN300-21680273
Q143263
BRD-K03039262-001-03-7
45ED0A4C-6FDA-443F-B886-D6C805A76AF2
Ergosterol, 10 mg/mL in chloroform, analytical standard
(3beta,14beta,17alpha,22E)-ergosta-5,7,22-trien-3-ol
Ergosterol, European Pharmacopoeia (EP) Reference Standard
Ergosterol, United States Pharmacopeia (USP) Reference Standard
ERGOSTEROL (CONSTITUENT OF GANODERMA LUCIDUM FRUITING BODY) [DSC]
Ergosterol, Pharmaceutical Secondary Standard
Certified Reference Material
(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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]
- Nagia MM, El-Metwally MM, et al. (2012). Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Organic and Medicinal Chemistry Letters,2012,2(1),9. [View] [PubMed]
- Ebrahim W, El-Neketi M, et al. (2016). Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal−bacterial mixed cultures. Journal of Natural Products,2016,79,914-922. [View] [PubMed]
Pubchem:
444679
Cas:
57-87-4
Gnps:
CCMSLIB00006393512
Zinc:
ZINC000004084618
Kegg Ligand:
C01694
Chebi:
16933
Nmrshiftdb2:
60018462
Metabolights:
MTBLC16933
Chembl:
CHEMBL1232562
Comptox:
DTXSID90878679
Drugbank:
DB04038
Pdb Ligand:
ERG
Bindingdb:
50378884
Selleck:
Ergosterol
CPRiL:
5633
SMILES: C1CCC(C12)CCC3C2=CC=C4C3CCCC4
Level: 0
Mol. Weight: 396.66 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.55
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.83
- Plasma Protein Binding
- 83.96
- 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
- Non-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
- 5.94
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.46
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.13
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.21
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -20.57
- Rat (Acute)
- 3.32
- Rat (Chronic Oral)
- 1.85
- Fathead Minnow
- 4.21
- 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
- 408.83
- Hydration Free Energy
- -3.92
- Log(D) at pH=7.4
- 6.06
- Log(P)
- 8.24
- Log S
- -6.96
- Log(Vapor Pressure)
- -6.86
- Melting Point
- 155.16
- pKa Acid
- 12.38
- pKa Basic
- 7.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9362 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9362 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9274 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9274 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9237 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9237 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9180 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9180 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9127 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9127 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9097 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9097 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9091 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9091 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9071 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9071 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.9013 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.9013 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8846 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8846 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8783 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8783 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8774 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8774 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8762 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8762 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8680 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8680 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8592 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8592 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8334 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8334 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8277 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8277 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8251 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8251 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.8212 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.8212 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.8207 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.8207 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.8107 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.8107 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8029 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8029 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7998 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7998 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.7826 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.7826 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7806 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7806 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7790 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7790 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7700 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7700 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7591 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7591 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7564 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7564 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7539 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7539 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7526 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7526 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7508 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7508 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7504 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7504 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7501 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7501 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7497 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7497 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7463 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7463 |
| Beta-elicitin cinnamomin | P15569 | ELIB_PHYCI | Phytophthora cinnamomi | 4 | 0.7330 |
| Beta-elicitin cinnamomin | P15569 | ELIB_PHYCI | Phytophthora cinnamomi | 4 | 0.7330 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7254 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7254 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7151 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7151 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7140 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7140 |