Lupeol - Compound Card

Lupeol

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Lupeol

Structure
Zoomed Structure
  • 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

  • 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
Kegg Ligand: C08628
Chebi: 6570
Nmrshiftdb2: 70127541
Metabolights: MTBLC6570
Drugbank: DB12622
Bindingdb: 50377927
CPRiL: 62207
Structure

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

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