Betulinic acid - Compound Card

Betulinic acid

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Betulinic acid

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • 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)CC[C@@H](C1(C)C)O)C(=O)O
InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChIKey QGJZLNKBHJESQX-FZFNOLFKSA-N
Formula C30H48O3
HBA 2
HBD 2
MW 456.71
Rotatable Bonds 2
TPSA 57.53
LogP 7.09
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 456.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Jacaranda mimosaefolia Bignoniaceae Plantae 185774
2 Diospyros mespiliformis Euphorbiaceae Plantae 413760
3 Croton zambiescus Euphorbiaceae Plantae 323089
4 Ficus auriculata Moraceae Plantae 100541
5 Melaleuca ericifolia Myrtaceae Plantae 73757
6 Albizia coriaria Leguminosae/Fabaceae Plantae 2708711
7 Thespesia garckeana Malvaceae Plantae 1833803
8 Lantana viburnoides sp viburnoides var kisi Verbenaceae Plantae 87005
9 Cussonia bancoensis Araliaceae Plantae 2708779
10 Baillonella toxisperma (Pierre) Sapotaceae Plantae 568230

Showing of synonyms

  • Masila VM, Midiwo JO, et al. (2015). Anti-vancomycin-resistant Enterococcus faecium and E. faecalis activities of (-)-gossypol and derivatives from Thespesia garckeana.. Natural Product Communications,2015,10(4),613-616. [View] [PubMed]
  • Abdel Bar FM, Zaghloul AM, et al. (2008). Antiproliferative triterpenes from Melaleuca ericifolia. Journal of Natural Products,2008,71(10),1787-1790. [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]
  • Pierre Yemback, Kenneth O. Eyong, et al. (2023). Lupane derivatives: Design, isolation, synthesis and evaluation of antiplasmodial activity against Plasmodium falciparum 3D7 strain. Phytochemistry Letters, 2023, 57, 26-35. [View]
  • Innocent E, Joseph CC, et al. (2008). Mosquito larvicidal constituents from Lantana viburnoides sp viburnoides var kisi (A. rich) Verdc (Verbenaceae). Journal of Vector Borne Diseases,2008,45(3),240-244. [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]
  • Tapondjou LA, Lontsi D, et al. (2003). Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production. J Nat Prod. 2003, 66(9), 1266-1269. [View]
Pubchem: 64971
Kegg Ligand: C08619
Chebi: 3087
Nmrshiftdb2: 40265324
Metabolights: MTBLC3087
Drugbank: DB12480
Pdb Ligand: 06L
Bindingdb: 23208
CPRiL: 55981
Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 456.71 g/mol

Antibacterial
Antimalarial

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.02
Plasma Protein Binding
94.31
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
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.95
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
3.7
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-111.16
Rat (Acute)
2.48
Rat (Chronic Oral)
2.12
Fathead Minnow
3.86
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
461.13
Hydration Free Energy
-2.54
Log(D) at pH=7.4
5.23
Log(P)
6.71
Log S
-6.44
Log(Vapor Pressure)
-9.52
Melting Point
263.13
pKa Acid
5.99
pKa Basic
8.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8220
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8220
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7894
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7894
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7509
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7509
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7013
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7013

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