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Fucosterol
- Family: Plantae - Sargassaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | C/C=C(/C(C)C)\CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C |
|---|---|
| InChI | InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7+/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1 |
| InChIKey | OSELKOCHBMDKEJ-JUGJNGJRSA-N |
| Formula | C29H48O |
| HBA | 1 |
| HBD | 1 |
| MW | 412.7 |
| Rotatable Bonds | 5 |
| TPSA | 20.23 |
| LogP | 7.94 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 412.37 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cystoseira foeniculacea | Sargassaceae | Plantae | 590109 |
Showing of synonyms
Fucosterol
17605-67-3
(24E)-24-N-Propylidenecholesterol
Stigmasta-5,24(28)-dien-3-ol, (3beta,24E)-
UNII-504ZAM710C
24E-ethylidene-cholest-5-en-3beta-ol
(3beta,24E)-Stigmasta-5,24(28)-dien-3-ol
Stigmasta-5,24-dien-3beta-ol
CHEBI:27865
(E)-Stigmasta-5,24(28)-dien-3beta-ol
504ZAM710C
FUCOSTEROL [MI]
(24E)-stigmasta-5,24(28)-dien-3beta-ol
Stigmasta-5,24(28)-dien-3-ol, (3.beta.,24E)-
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Stigmasta-5,24(28)-dien-3.beta.-ol, (E)-
Delta(5)-avenasterol
24-Isoethylidenecholest-5-en-3beta-ol, delta(5)-avenasterol
(3beta,24E)-stigmasta-5,24(28)-dien-ol
Trans-D5-Avenosterol
18472-36-1
(24E)-Ethylidenecholesterol
(E)-24-Ethylidenecholesterol
Fucosterol, (3beta)-isomer
(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((E,2R)-5-propan-2-ylhept-5-en-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-ol
(7s,9ar,11ar)-1-((2r,5e)-5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta(a)phenanthren-7-ol
(7S,9AR,11AR)-1-[(2R,5E)-5-ISOPROPYLHEPT-5-EN-2-YL]-9A,11A-DIMETHYL-1H,2H,3H,3AH,3BH,4H,6H,7H,8H,9H,9BH,10H,11H-CYCLOPENTA[A]PHENANTHREN-7-OL
Stigmasta-5,24(28)-dien-3beta (E)--ol
FUCOSTEROL [INCI]
Fucosterol, 28-(14)C-labeled cpd, (E)-isomer
24E-Ethylidene-cholest-5-en-3b-ol
24E-Ethylidene-cholest-5-en-3I2-ol
(e)-Stigmasta-5,24(28)-dien-3I2-ol
(3b,24E)-Stigmasta-5,24(28)-dien-ol
Stigmasta-5,24(28)-dien-3beta-ol, (E)-
26575-12-2
(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-((z,2r)-5-propan-2-ylhept-5-en-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta(a)phenanthren-3-ol
(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(z,2r)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol
24-isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterol
24z-ethylidenecholest-5-en-3b-ol
28-isofucosterol
Oselkochbmdkej-jugjngjrsa-n
Oselkochbmdkej-wgmizeqosa-n
Stigmasta-5,24-dien-3 beta-ol
Fucosterin
Trans-24-Ethylidenecholesterol
(3ss,24E)-Stigmasta-5,24(28)-dien-3-ol
Trans-Stigmasta-5,24(28)dien-3ss-ol
24(E)-Ethylidenecholest-5-en-3.beta.-ol
SCHEMBL94291
CHEMBL519971
DTXSID701033229
MSK13005
5,24(28)e-stigmastadien-3beta-ol
LMST01040255
AKOS040759328
BP-40653
C08817
E80778
Stigmasta-5,24(28)-dien-3-ol, (3|A,24E)-
Q15410971
B09778B9-3283-4EDE-A260-309F18C200C0
Fucosterol(24E)-24-N-Propylidenecholesterol
- Bouzidi N, Viano Y, et al. (2019). Sterols from the brown alga Cystoseira foeniculacea: Degradation of fucosterol into saringosterol epimers.. Arabian Journal of Chemistry, 2019, 12(7), 1474-1478. [View]
Pubchem:
5281328
Cas:
17605-67-3
Gnps:
CCMSLIB00006461607
Zinc:
ZINC000004097814
Kegg Ligand:
C08817
Chebi:
27865
Nmrshiftdb2:
60018475
Metabolights:
MTBLC27865
Chembl:
CHEMBL519971
CPRiL:
11920
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 412.7 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.5
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.91
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.8
- Plasma Protein Binding
- 83.37
- 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
- 7.71
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.3
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.45
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.34
- 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
- -32.01
- Rat (Acute)
- 2.23
- Rat (Chronic Oral)
- 1.87
- Fathead Minnow
- 4.1
- 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
- 405.74
- Hydration Free Energy
- -3.81
- Log(D) at pH=7.4
- 6.16
- Log(P)
- 8.25
- Log S
- -6.8
- Log(Vapor Pressure)
- -7.15
- Melting Point
- 144.54
- pKa Acid
- 13.49
- pKa Basic
- 8.05
| 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 | 0.9388 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9262 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9227 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9191 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9118 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9096 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9001 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8820 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8678 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8671 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8663 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8626 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8625 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8544 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8422 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8293 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8209 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8200 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8015 |
| Lanosterol 14-alpha-demethylase | Q385E8 | Q385E8_TRYB2 | Trypanosoma brucei brucei | 4 | 0.7990 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 5 | 0.7940 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7919 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7777 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7751 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7542 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7530 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.7469 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7357 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7272 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7270 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7262 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7207 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.7146 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 4 | 0.7142 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7117 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7057 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7042 |