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Lupeol
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | CC(=C)[C@@H]1CC[C@]2(C1[C@@]1(C)CCC3[C@@]([C@@]1(CC2)C)(C)CCC1[C@]3(C)CC[C@@H](C1(C)C)O)C |
|---|---|
| InChI | InChI=1S/C31H52O/c1-20(2)21-10-14-27(5)18-19-31(9)29(7)16-11-22-26(3,4)24(32)13-15-28(22,6)23(29)12-17-30(31,8)25(21)27/h21-25,32H,1,10-19H2,2-9H3/t21-,22?,23?,24-,25?,27+,28-,29+,30+,31-/m0/s1 |
| InChIKey | OBPSJJZSNBBGAY-LFLJYNPASA-N |
| Formula | C31H52O |
| HBA | 1 |
| HBD | 1 |
| MW | 440.76 |
| Rotatable Bonds | 1 |
| TPSA | 20.23 |
| LogP | 8.41 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.94 |
| Exact Mass | 440.4 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Periploca laevigata | Apocynaceae | Plantae | 413294 |
Showing of synonyms
Lupeol
545-47-1
Fagarasterol
Clerodol
Monogynol B
Fagarsterol
Lupenol
Farganasterol
Triterpene lupeol
Beta-Viscol
UNII-O268W13H3O
Lup-20(29)-en-3beta-ol
CHEBI:6570
(+)-Lupeol
Lup-20(29)-en-3-ol, (3-beta)-
HSDB 7687
O268W13H3O
EINECS 208-889-9
NSC 90487
NSC-90487
(3-beta)-Lup-20(29)-en-3-ol
LUPEOL, (+)-
Lup-20(29)-en-3-beta-ol
(3beta)-lup-20(29)-en-3-ol
Lup-20(29)-en-3-ol
3beta-HYDROXYLUP-20(29)-ENE
208-889-9
Lup-20(29)-en-3-ol, (3b)-
Lup-20(29)-en-3b-ol
.beta.-Viscol
MFCD00017351
20(29)-Lupen-3beta-ol
NSC90487
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Lup-20(29)-en-3-ol, (3.beta.)-
Lup-20(29)-en-3.beta.-ol
Lupeol (Standard)
Lup-20(29)-en-3-ol, (3beta)-
LUPEOL [HSDB]
LUPEOL [MI]
Lupeol, >=94%
Lupeol, analytical standard
SCHEMBL148518
CHEMBL289191
HY-N0790R
3beta-lup-20(29)-en-3-ol
DTXSID901025006
HY-N0790
MSK40145
BDBM50377927
S3614
AKOS016008524
CCG-268968
CS-7563
DB12622
DS-3391
FL16230
LMPR0106130001
NCGC00168853-06
NCGC00168853-07
1ST40145
NCI60_042005
3.BETA.-HYDROXYLUP-20(29)-ENE
LUP-20(29)-EN-3-.BETA.-OL
L0321
NS00043298
C08628
(3-.BETA.)-LUP-20(29)-EN-3-OL
Q409366
LUP-20(29)-EN-3-OL, (3-.BETA.)-
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
- Ben nejma A, Besbes M, et al. (2013). Isolation and structure elucidation of acetylcholinesterase lipophilic lupeol derivatives inhibitors from the latex of the Tunisian Periploca laevigata. Arabian Journal of Chemistry,2013,in press. [View]
Pubchem:
259846
Cas:
545-47-1
Gnps:
CCMSLIB00006580270
Zinc:
ZINC000004081455
Kegg Ligand:
C08628
Chebi:
6570
Nmrshiftdb2:
70127541
Metabolights:
MTBLC6570
Chembl:
CHEMBL289191
Drugbank:
DB12622
Bindingdb:
50377927
CPRiL:
62207
SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5
Level: 0
Mol. Weight: 440.76 g/mol
Anti-acetylcholinesterase
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.47
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.65
- Plasma Protein Binding
- 83.85
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- 10.72
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.1
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.92
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.14
- 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
- Toxic
- T. Pyriformis
- -60.18
- Rat (Acute)
- 2.28
- Rat (Chronic Oral)
- 1.28
- Fathead Minnow
- 4.04
- 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
- 396.96
- Hydration Free Energy
- -2.88
- Log(D) at pH=7.4
- 7.55
- Log(P)
- 8.68
- Log S
- -7.26
- Log(Vapor Pressure)
- -7.9
- Melting Point
- 229.8
- pKa Acid
- 13.29
- pKa Basic
- 8.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7895 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7895 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7842 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7842 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7669 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7669 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7375 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7375 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7364 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7364 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7301 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7301 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7262 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7262 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7200 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.7200 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7183 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7183 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7002 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7002 |