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(22R,23S)-17alpha,23-epoxy-3beta,22,24epsilon-trihydroxy-27,28-bisnor-lanost-8-ene
- Family: Plantae - Hyacinthaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Nortriterpenoid
| Canonical Smiles | CCC([C@@H]1O[C@]2([C@H]([C@@H]1O)C)CC[C@@]1([C@]2(C)CCC2=C1CC[C@@H]1[C@]2(C)CC[C@@H]([C@@H]1C)O)C)O |
|---|---|
| InChI | InChI=1S/C28H46O4/c1-7-21(29)24-23(31)17(3)28(32-24)15-14-26(5)20-9-8-18-16(2)22(30)11-12-25(18,4)19(20)10-13-27(26,28)6/h16-18,21-24,29-31H,7-15H2,1-6H3/t16-,17+,18+,21?,22+,23+,24+,25+,26+,27+,28+/m1/s1 |
| InChIKey | RCRAOVCUQYSARF-ZHUAWOTDSA-N |
| Formula | C28H46O4 |
| HBA | 4 |
| HBD | 3 |
| MW | 446.67 |
| Rotatable Bonds | 2 |
| TPSA | 69.92 |
| LogP | 5.0 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 446.34 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Merwilla natalensis | Hyacinthaceae | Plantae | 205725 |
Showing of synonyms
(22R,23S)-17alpha,23-epoxy-3beta,22,24epsilon-trihydroxy-27,28-bisnor-lanost-8-ene
- Moodley N, Mulholland DA, et al. (2004). Eucosterol-Type Nortriterpenoids from Merwilla natalensis. Journal of natural products, 2004, 67(5), 918–920. [View]
No compound-protein relationship available.
SMILES: O1CCCC12C3C(CC2)C4=C(CC3)C5C(CC4)CCCC5
Level: 0
Mol. Weight: 446.67 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.06
- Plasma Protein Binding
- 77.9
- 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
- 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
- 14.69
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.83
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.67
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.63
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- 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
- -91.24
- Rat (Acute)
- 2.54
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.77
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 447.93
- Hydration Free Energy
- -3.18
- Log(D) at pH=7.4
- 4.21
- Log(P)
- 5.16
- Log S
- -5.42
- Log(Vapor Pressure)
- -8.91
- Melting Point
- 211.4
- pKa Acid
- 11.87
- pKa Basic
- 7.38
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8810 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8611 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8290 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7996 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7891 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7682 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7599 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7289 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.7000 |