Pristimerin - Compound Card

Pristimerin

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Pristimerin

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Quinonemethide Triterpene
Canonical Smiles COC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC=C4C3=CC(=O)C(=C4C)O)[C@]1(CC2)C)C)C
InChI InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1
InChIKey JFACETXYABVHFD-WXPPGMDDSA-N
Formula C30H40O4
HBA 4
HBD 1
MW 464.65
Rotatable Bonds 1
TPSA 63.6
LogP 6.79
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 464.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Maytenus senegalensis Celastraceae Plantae 256095

Showing of synonyms

  • Khalid SA, Friedrichsen GM, et al. (2007). Isolation and characterization of pristimerin as the antiplasmodial and antileishmanial agent of Maytenus senegalensis (Lam.) Exell.. Arkivoc,2007,2007(ix),129-134. [View]
Pubchem: 159516
Kegg Ligand: C08633
Chebi: 8416
Nmrshiftdb2: 60066130
Drugbank: DB17049
Bindingdb: 50481947

No compound-protein relationship available.

Structure

SMILES: C1C(=O)C=CC(C=12)=CC=C3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 464.65 g/mol

Anti-leishmanial
Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.040
Plasma Protein Binding
99.44
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.350
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.390
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.920
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
Toxic
T. Pyriformis
-155.650
Rat (Acute)
2.470
Rat (Chronic Oral)
2.380
Fathead Minnow
4.220
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
504.240
Hydration Free Energy
-2.870
Log(D) at pH=7.4
5.170
Log(P)
5.61
Log S
-6.44
Log(Vapor Pressure)
-7.91
Melting Point
246.85
pKa Acid
9.03
pKa Basic
4.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7531
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7531
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7192
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7189

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