Select a section from the left sidebar
Lupeol
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
Canonical Smiles | CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(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/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1 |
InChIKey | MQYXUWHLBZFQQO-QGTGJCAVSA-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 | Periploca laevigata | Apocynaceae | Plantae | 413294 |
2 | Jacaranda mimosaefolia | Bignoniaceae | Plantae | 185774 |
3 | Boswellia carterii | Burseraceae | Plantae | 80276 |
4 | Diospyros mespiliformis | Euphorbiaceae | Plantae | 413760 |
5 | Croton zambiescus | Euphorbiaceae | Plantae | 323089 |
6 | Ficus auriculata | Moraceae | Plantae | 100541 |
7 | Centaurea omphalotricha | Asteraceae | Plantae | 41503 |
8 | Launaea arborescens | Asteraceae | Plantae | 43199 |
9 | Lactuca sativa | Asteraceae | Plantae | 4236 |
10 | Reichardia tingitana | Asteraceae | Plantae | 43208 |
11 | Sonchus macrocarpus | Asteraceae | Plantae | 2984305 |
12 | Lannea alata | Anacardiaceae | Plantae | 289715 |
13 | Aloe barbadensis | Asphodelaceae | Plantae | 34199 |
14 | Boswellia species | Burseraceae | Plantae | 173701 |
15 | Garcinia edulis | Clusiaceae-Guttiferae | Plantae | 58227 |
16 | Escinops ellenbeckii | Asteraceae | Plantae | — |
17 | Antidesma venosum | Euphorbiaceae | Plantae | 992644 |
18 | Croton megalocarpoides | Euphorbiaceae | Plantae | 1704624 |
19 | Croton macrostachyus | Euphorbiaceae | Plantae | 1704622 |
20 | Millettia oblata | Leguminosae/Fabaceae | Plantae | 3090232 |
21 | Albizia coriaria | Leguminosae/Fabaceae | Plantae | 2708711 |
22 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
23 | Teclea simplicifolia | Rutaceae | Plantae | 482953 |
24 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
25 | Zanthoxylum gilletii | Rutaceae | Plantae | 1291627 |
26 | Zanthoxylum gilletii | Rutaceae | Plantae | 1291627 |
27 | Symphonia globulifera | Clusiaceae | Plantae | 156483 |
28 | Tetracera potatoria | Dilleniaceae | Plantae | 85284 |
29 | Fagara heitzii | Rutaceae | Plantae | — |
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
- Derese S, Barasa L, et al. (2014). 4'-Prenyloxyderrone from the stem bark of Millettia oblata ssp. teitensis and the antiplasmodial activities of isoflavones from some Millettia species.. Phytochemistry Letters,2014,31(8),69-72. [View] [PubMed]
- Magadula JJ. (2010). A bioactive isoprenylated xanthone and other constituents of Garcinia edulis. Fitoterapia,2010,81(5),420-423. [View] [PubMed]
- Magadula JJ, Mwangomo DT, et al. (2013). A novel gama-lactone and other constituents of a Tanzanian Antidesma venosum. Spatula DD,2013,3(1),7-12. [View] [PubMed]
- Abdel-Mogib M, Awad SN, et al. (1993). A sesquiterpene glucoside from Reichardia tingitana. Phytochemistry,1993,34(5),1434-1435. [View]
- Hymete A, Rohloff J, et al. (2005). Acetylenic thiophenes from the roots of Escinops ellenbeckii from Ethiopia. Natural Product Research,2005,19(8),755-761. [View] [PubMed]
- Okoth DA, Chenia HY, et al. (2013). Antibacterial and antioxidant activities of flavonoids from Lannea alata (Engl.) Engl. (Anacardiaceae). Phytochemistry Letters,2013,6(3),476-481. [View]
- Weenen H, Nkunya MH, et al. (1990). Antimalarial compounds containing an alpha,beta-unsaturated carbonyl moiety from Tanzanian medicinal plants.. Planta medica,1990,56(4),371-373. [View] [PubMed]
- Byamukama R, Barbara G, et al. (2015). Bioactive compounds in the stem bark of Albizia coriaria (Welw. ex Oliver).. International Journal of Biological and Chemical Sciences,2015,9(2),1013-1024. [View] [PubMed]
- Mohamed LE, El-Nur EE, et al. (2009). Bioactive natural products from two Sudanese medicinal plants Diospyros mespiliformis and Croton zambesicus. Records of Natural Products,2009,3(4),198-203. [View]
- Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
- Mouffok S, Haba H, et al. (2012). Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab.. Records of Natural Products,2012,6(3),292-295. [View]
- Nguengang RT, Tchegnitegni BT, et al. (2023). Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities. Molecules. 2023, 28(6), 2473. [View] [PubMed]
- Nyaboke HO, Moraa M, et al. (2018). Cytotoxicity of lupeol from the stem bark of Zanthoxylum gilletii against multi-factorial drug resistant cancer cell lines. Investigational Medicinal Chemistry and Pharmacology,2018,1(1),10.. [View] [PubMed]
- Morikawa T, Oominami H, et al. (2010). Four new ursane-type triterpenes, olibanumols K, L, M, and N, from Traditional Egyptian Medicine olibanum, the gum-resin of Boswellia carterii. Chemical and Pharmaceutical Bulletin,2010,58(11),1541-1544. [View] [PubMed]
- Askri M, Mighri Z, et al. (1989). Medicinal plants of Tunisia. the structure of periplocadiol, a new elemane-type sesquiterpene isolated from the roots of Periploca laevigata. Journal of Natural Products,1989,52(4),792-796. [View]
- Ndunda B, Langat MK, et al. (2016). New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis and M. G. Gilbert.. Planta Med,2016,82(11-12),1079-1086. [View] [PubMed]
- Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]
- Zaghloul AM, Gohar AA, et al. (2011). Phenylpropanoids from the stem bark of Jacaranda mimosaefolia. Natural Product Research,2011,25(1),68-76. [View] [PubMed]
- Al Fishawy A, Zayed R, et al. (2011). Phytochemical and pharmacological studies of Ficus auriculata Lour. (Moraceae) cultivated in Egypt. Planta Medica,2011,77-PL19. [View]
- Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
- Njeru DN, Derese S, et al. (2015). Phytochemical investigation of the stem bark and the leaves of Teclea simplicifolia for analgesic activity. M.Sc. Thesis-1, University of Nairobi, Kenya,2015. [View] [PubMed]
- Yibralign Z, Fiseha A. (2007). Phytochemical investigation on the stem bark of Croton macrostachyus (Bisana). M.Sc. Thesis, Addis Ababa University, Ethiopia,2007. [View] [PubMed]
- Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
- Kiplimo JJ, Shahidul Islam M, et al. (2012). Ring A-seco limonoids and flavonoids from the Kenyan Vepris uguenensis Engl. and their antioxidant activity. Phytochemistry,2012,83(2012),136-143. [View] [PubMed]
- Fomogne-Fodjo MC, Ndinteh DT, et al. (2017). Secondary metabolites from Tetracera potatoria stem bark with anti-mycobacterial activity.. Journal of ethnopharmacology,2017, 195, 238-245. [View] [PubMed]
- Mahmoud ZF, Kassem FF, et al. (1986). Sesquiterpene lactones from Lactuca sativa. Phytochemistry,1986,25(3),141-748. [View]
- Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
- Mahmoud Z, El-Masry S, et al. (1983). Two eudesmanolides from Sonchus macrocarpus. Phytochemistry,1983,22(5),1290-1291. [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
Alpha-glucosidase inhibitory
Anti-plasmodial
Anticancer
Antimicrobial
Suppressive on phagocytosis response upon activation with serum
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
- -2.77
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.69
- Plasma Protein Binding
- 87.89
- 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
- 11.9
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.56
- 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
- Toxic
- Daphnia Maga
- 5.97
- 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
- -43.61
- Rat (Acute)
- 2.29
- Rat (Chronic Oral)
- 1.41
- Fathead Minnow
- 3.92
- 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
- 398.07
- Hydration Free Energy
- -3.23
- Log(D) at pH=7.4
- 7.78
- Log(P)
- 8.55
- Log S
- -7.17
- Log(Vapor Pressure)
- -8.0
- Melting Point
- 218.75
- pKa Acid
- 13.28
- pKa Basic
- 8.08
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7858 |
Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7858 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7421 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7421 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7105 |
Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7105 |