Lupenone - Compound Card

Lupenone

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Lupenone

Structure
Zoomed Structure
  • Family: Plantae - Ericaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
InChI InChI=1S/C30H48O/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/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
InChIKey GRBHNQFQFHLCHO-BHMAJAPKSA-N
Formula C30H48O
HBA 1
HBD 0
MW 424.71
Rotatable Bonds 1
TPSA 17.07
LogP 8.23
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 424.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Diospyros mespiliformis Euphorbiaceae Plantae 413760
2 Albizia coriaria Leguminosae/Fabaceae Plantae 2708711
3 Angylocalyx oligophyllus Leguminosae/Fabaceae Plantae 1295187
4 Entandrophragma congoënse Meliaceae Plantae 2590899
5 Entandrophragma congoense Meliaceae Plantae 2590899
6 Fagara heitzii Rutaceae Plantae —
7 Erica multiflora Ericaceae Plantae 270440

Showing of synonyms

  • Happi GM, Kouam SF, et al. (2015). Antiplasmodial and Cytotoxic Triterpenoids from the Bark of the Cameroonian Medicinal Plant Entandrophragma congoënse.. Journal of natural products,2015, 78(4), 604-614. [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]
  • Villareal M.O, Han J, et al. (2013). Lupenone from Erica multiflora Leaf Extract Stimulates Melanogenesis in B16 Murine Melanoma Cells through the Inhibition of ERK1/2 Activation.. Planta medica, 2013, 79(3-4), 236-43. [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]
  • Kweka Wakeu B, Talla R, et al. (2022). Phytochemical analysis of the stems of Angylocalyx oligophyllus (Baker) Baker f. (Fabaceae). Biochemical Systematics and Ecology, 2022, 101, 104382. [View]
Pubchem: 92158
Kegg Ligand: C16990
Chebi: 67823
Nmrshiftdb2: 70068821
Metabolights: MTBLC67823
Bindingdb: 50241944
CPRiL: 100881
Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCC(=O)C5

Level: 0

Mol. Weight: 424.71 g/mol

Alpha-glucosidase inhibitory
Anti-plasmodial
Inhibition of erk1/2 activation
Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.19
Plasma Protein Binding
89.47
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
11.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.82
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.63
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.06
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
-42.11
Rat (Acute)
2.06
Rat (Chronic Oral)
1.37
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
424.63
Hydration Free Energy
-3.32
Log(D) at pH=7.4
7.49
Log(P)
7.97
Log S
-6.73
Log(Vapor Pressure)
-7.82
Melting Point
204.87
pKa Acid
12.45
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8935
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8935
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8624
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8624
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8017
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8017
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7832
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7832
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7288
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7288
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7271
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7271
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7154
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7154
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7049
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7049

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