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Ergosta-4,6,8(14),22-tetraen-3-one
- Family: Plantae - Guttiferae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | CC([C@H](/C=C/[C@H]([C@H]1CCC2=C3[C@H](CC[C@]12C)[C@@]1(C)CCC(=O)C=C1C=C3)C)C)C |
|---|---|
| InChI | InChI=1S/C28H40O/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/h7-10,17-20,24,26H,11-16H2,1-6H3/b8-7+/t19-,20+,24+,26-,27-,28+/m0/s1 |
| InChIKey | OIMXTYUHMBQQJM-HSVWHVBGSA-N |
| Formula | C28H40O |
| HBA | 1 |
| HBD | 0 |
| MW | 392.63 |
| Rotatable Bonds | 4 |
| TPSA | 17.07 |
| LogP | 7.46 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.68 |
| Exact Mass | 392.31 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pentadesma butyracea | Guttiferae | Plantae | 198785 |
Showing of synonyms
Ergosta-4,6,8(14),22-tetraen-3-one
19254-69-4
Ergosta-4,6,8(14),22-tetraen-3-one, (22E)-
Ergone
UNII-RI51Y55U8P
RI51Y55U8P
(9R,10R,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,9,11,12,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
CHEBI:69431
(22e,24r)-ergosta-4,6,8(14),22-tetraen-3-one
24-methylcholesta-4,6,8(14),22-tetraen-3-one
(22E)-4,6,8(14),22-ERGOSTATETRAEN-3-ONE
(9R,10R,13R,17R)-17-((E,2R,5R)-5,6-dimethylhept-3-en-2-yl)-10,13-dimethyl-1,2,9,11,12,15,16,17-octahydrocyclopenta(a)phenanthren-3-one
10,13-dimethyl-17-(1,4,5-trimethyl-hex-2-enyl)-1,2,9,10,11,12,13,15,16,17-decahydrocyclopenta(a)phenanthren-3-one
10,13-dimethyl-17-(1,4,5-trimethyl-hex-2-enyl)-1,2,9,10,11,12,13,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Oimxtyuhmbqqjm-bqyqjahwsa-n
(22E)-Ergosta-4,6,8(14),22-tetraen-3-one
SCHEMBL6365010
CHEMBL3588948
DTXSID201296846
HY-N3842
NSC785136
AKOS022184779
FE42617
NSC-785136
DA-69028
FS-10533
Q27104972
- Tala M, Wabo H, et al. (2013). A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea. Phytochemistry Letters, 2013, 6(3), 326-330. [View]
Pubchem:
6441416
Cas:
19254-69-4
Zinc:
ZINC000005761087
Chebi:
69431
Nmrshiftdb2:
60027120
Metabolights:
MTBLC69431
Chembl:
CHEMBL3588948
No compound-protein relationship available.
SMILES: C1CC(=O)C=C(C=C2)C1C(C2=C34)CCC3CCC4
Level: 0
Mol. Weight: 392.63 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.14
- Plasma Protein Binding
- 91.16
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 2.88
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.01
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.63
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.9
- 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
- -18.78
- Rat (Acute)
- 2.5
- Rat (Chronic Oral)
- 1.6
- Fathead Minnow
- 4.72
- 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
- 437.42
- Hydration Free Energy
- -4.46
- Log(D) at pH=7.4
- 5.55
- Log(P)
- 7.32
- Log S
- -6.58
- Log(Vapor Pressure)
- -6.59
- Melting Point
- 126.59
- pKa Acid
- 11.31
- pKa Basic
- 5.51
| 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 | 0.9692 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9453 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9149 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9077 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9046 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9004 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.8509 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.8414 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.8404 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8139 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8128 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7868 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7858 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7791 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7389 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7292 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7273 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7201 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7162 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7128 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7126 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7105 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7101 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7059 |