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Lanosterol
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)C |
|---|---|
| InChI | InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1 |
| InChIKey | CAHGCLMLTWQZNJ-BQNIITSRSA-N |
| Formula | C30H50O |
| HBA | 1 |
| HBD | 1 |
| MW | 426.73 |
| Rotatable Bonds | 4 |
| TPSA | 20.23 |
| LogP | 8.48 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.87 |
| Exact Mass | 426.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Campanula medium | Campanulaceae | Plantae | 56154 |
| 2 | Euphorbia guyoniana | Euphorbiaceae | Plantae | 1138347 |
Showing of synonyms
Lanosterol
Lanosterin
Lanster
Botalan base 138
Lanosta-8,24-dienol
(3beta)-lanosta-8,24-dien-3-ol
Kryptosterol
Lanosta-8,24-dien-3beta-ol
Lanostereol
Botalan base
Lanostadien-3-beta-ol
CHEBI:16521
Lanosta-8,24-dien-3-ol, (3.beta.)-
NSC 60677
UNII-1J05Z83K3M
Lanosta-8,24-dien-3-ol, (3beta)-
Lanosta-8,24-dien-3-beta-ol
Lanosta-8,24-dien-3.beta.-ol
1J05Z83K3M
LANOSTEROL [MI]
EINECS 201-214-9
NSC-60677
(3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
(3-beta)-Lanosta-8,24-dien-3-ol
(3.beta.)-Lanosta-8,24-dien-3-ol
BRN 2226449
AI3-23643
DTXSID1040744
4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol
Lanosta-8,24-dien-3-ol, (3-beta)-
(3beta,20R)-Lanosta-8,24-dien-3-ol
Cholesta-8,24-dien-3-ol, 4,4,14-trimethyl-, (3beta,5alpha)-
Cholesta-8,24-dien-3-ol, 4,4,14-trimethyl-, (3.beta.,5.alpha.)-
(3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol
4,4,14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol
(3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R)-6-methylhept-5-en-2-yl)-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-3-ol
LANOSTEROL [INCI]
DTXCID9020744
4,4,14 alpha-trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol
Lanosta-8,24-dien-3beta-ol (8CI)
201-214-9
4-06-00-04188 (beilstein handbook reference)
Cahgclmltwqznj-bqniitsrsa-n
Cahgclmltwqznj-liyszjhcsa-n
79-63-0
Cryptosterol
NSC60677
8,24-Lanostadien-3beta-ol
3beta-Hydroxy-8,24-lanostadiene
Lanosterol (Technical Grade)
Lanostcrol
Lanososterol
MFCD00021108
Lanosterol - 90%
Lanosta-8, (3.beta.)-
Lanosterol, >=93%, powder
SCHEMBL145834
CHEMBL225111
GTPL2746
GLXC-14819
BDBM50459238
LMST01010017
MSK164264
S4755
(3|A)-Lanosta-8,24-dien-3-ol
(3 beta)-Lanosta-8,24-dien-3-ol
AKOS024307002
DB03696
FL71051
HY-W020033
NCGC00164398-01
FL159528
MS-27534
1ST164264
CS-0031956
Lanosterol (Isocholesterol) - Lanosterol 60%
C01724
A929846
Q414996
(3alpha)-4,4,14-trimethyl-Cholesta-8,24-dien-3-ol
C4CA2F34-1C1A-4673-AC43-E547708CB228
Cholesta-8, 4,4,14-trimethyl-, (3.beta.,5.alpha.)-
(3beta,5alpha)-4,4,14-trimethyl-Cholesta-8,24-dien-3-ol
8,24-Lanostadiene-3?-ol
Isocholesterol
3?-Hydroxy-8,24-lanostadiene
(3S,5R,10S,13R,14R,17R)-17-[(1R)-1,5-dimethylhex-4-enyl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- Assiri AMA, Ramadan MF, et al. (2014). Bioactive compounds and antiradical potential of Campanula medium lipids.. Chemistry of Natural Compounds,2014,50(6),1088-1091. [View]
- Haba H, Lavaud C, et al. (2007). Diterpenoids and triterpenoids from Euphorbia guyoniana. Phytochemistry,2007,68,1255-1260. [View] [PubMed]
Pubchem:
246983
Cas:
79-63-0
Gnps:
CCMSLIB00010008010
Zinc:
ZINC000003870056
Kegg Ligand:
C01724
Chebi:
16521
Nmrshiftdb2:
60018505
Metabolights:
MTBLC16521
Chembl:
CHEMBL225111
Comptox:
DTXSID1040744
Drugbank:
DB03696
Pdb Ligand:
LAN
Bindingdb:
50459238
CPRiL:
971
SMILES: C1CCC(C12)CCC3=C2CCC4C3CCCC4
Level: 0
Mol. Weight: 426.73 g/mol
Antiradical potential
Absorption
- Caco-2 (logPapp)
- -4.86
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.52
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.55
- Plasma Protein Binding
- 90.38
- 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
- 8.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.51
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.01
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.53
- 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
- Safe
- T. Pyriformis
- -35.49
- Rat (Acute)
- 1.77
- Rat (Chronic Oral)
- 1.41
- Fathead Minnow
- 4.02
- 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
- 409.76
- Hydration Free Energy
- -3.88
- Log(D) at pH=7.4
- 6.98
- Log(P)
- 9.42
- Log S
- -6.95
- Log(Vapor Pressure)
- -7.01
- Melting Point
- 147.05
- pKa Acid
- 13.25
- pKa Basic
- 7.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8303 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8303 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8205 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8205 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7908 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7908 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7891 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7891 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.7386 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 4 | 0.7386 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7377 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7377 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7367 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7367 |