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24(28)-ergostene-3beta,6alpha-diol
- Family: Plantae - Anacardiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | O[C@H]1CC[C@]2(C(C1)[C@@H](O)CC1C2CC[C@]2(C1CCC2[C@@H](CCC(=C)C(C)C)C)C)C |
|---|---|
| InChI | InChI=1S/C28H48O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h17,19-26,29-30H,3,7-16H2,1-2,4-6H3/t19-,20+,21?,22?,23?,24?,25?,26+,27-,28-/m1/s1 |
| InChIKey | OIMWFEZCTFSFNB-PQQBMXOCSA-N |
| Formula | C28H48O2 |
| HBA | 2 |
| HBD | 2 |
| MW | 416.69 |
| Rotatable Bonds | 5 |
| TPSA | 40.46 |
| LogP | 6.61 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 416.37 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Antrocaryon klaineanum | Anacardiaceae | Plantae | 289695 |
| 2 | Antrocaryon klaineanum | Anacardiaceae | Plantae | 289695 |
Showing of synonyms
24(28)-ergostene-3beta,6alpha-diol
- DouanlaPD, Tabopda TK, et al. (2015). Antrocarines A-F, antiplasmodial ergostane steroids from the stem bark of Antrocaryon klaineanum.. Phytochemistry,2015, 117, 521-526. [View] [PubMed]
- Fouokeng Y, Akak CM, et al. (2017). The structure of antrocarine E, an ergostane isolated from Antrocaryon klaineanum Pierre (Anacardiaceae).. Fitoterapia,2017, 117, 61-64. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 416.69 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.49
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.47
- Plasma Protein Binding
- 70.27
- 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
- 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
- 11.11
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.72
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.53
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.56
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -30.09
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 2.08
- Fathead Minnow
- 3.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 401.61
- Hydration Free Energy
- -3.57
- Log(D) at pH=7.4
- 5.68
- Log(P)
- 6.84
- Log S
- -6.5
- Log(Vapor Pressure)
- -7.72
- Melting Point
- 174.92
- pKa Acid
- 12.29
- pKa Basic
- 8.47
| 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 | 0.9355 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9355 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9333 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9333 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9294 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9294 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.9156 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.9156 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9061 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9061 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9020 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9020 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9017 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9017 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9005 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9005 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.9002 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.9002 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.8983 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 5 | 0.8983 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8847 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8847 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8791 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8791 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8750 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8750 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8702 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8702 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8648 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8648 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8513 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8513 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8499 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8499 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8284 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8284 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8201 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8201 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8123 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8123 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.8110 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.8110 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7881 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7881 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.7868 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.7868 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7844 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7844 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7831 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7831 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7808 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7808 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7666 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7666 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7611 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7611 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7561 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7561 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7547 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7547 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7537 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7537 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7509 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7509 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7505 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7505 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7482 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7482 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7476 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7476 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.7452 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.7452 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7406 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7406 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7372 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7372 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7353 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7353 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7330 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7330 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7319 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7319 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7277 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P00189 | CP11A_BOVIN | Bos taurus | 3 | 0.7277 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7219 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7219 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7200 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7200 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7111 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7111 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7008 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7008 |