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Lupeol
- Family: Plantae - Sterculiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Pentacyclic Triterpenoid
| Canonical Smiles | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C |
|---|---|
| InChI | InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3 |
| InChIKey | MQYXUWHLBZFQQO-UHFFFAOYSA-N |
| Formula | C30H50O |
| HBA | 1 |
| HBD | 1 |
| MW | 426.73 |
| Rotatable Bonds | 1 |
| TPSA | 20.23 |
| LogP | 8.02 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 426.39 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cola lateritia | Sterculiaceae | Plantae | 577684 |
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
- Kamdem M, Ojo O, et al. (2022). Pentacyclic Triterpenoids, Phytosteroids and Fatty Acid Isolated from the Stem-bark of Cola lateritia K. Schum. (Sterculiaceae) of Cameroon origin; Evaluation of Their Antibacterial Activity. Arabian Journal of Chemistry, 2022, 15(1), 103506. [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: 426.73 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.42
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.69
- Plasma Protein Binding
- 23.98
- 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
- 11.22
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.88
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.93
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- 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
- Safe
- T. Pyriformis
- -36.38
- Rat (Acute)
- 2.31
- Rat (Chronic Oral)
- 1.37
- Fathead Minnow
- 4.83
- 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
- 381.04
- Hydration Free Energy
- -3.34
- Log(D) at pH=7.4
- 7.47
- Log(P)
- 8.19
- Log S
- -7.29
- Log(Vapor Pressure)
- -7.48
- Melting Point
- 225.49
- pKa Acid
- 13.46
- pKa Basic
- 8.21
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7939 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7798 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7618 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7449 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7433 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7424 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7329 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.7078 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7044 |