Icajine - Compound Card

Icajine

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Icajine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoindole Alkaloid
Canonical Smiles CN1CC[C@]23C(=O)C[C@H]4C(=CCO[C@@H]5[C@H]4[C@@H]3N(c3c2cccc3)C(=O)C5)C1
InChI InChI=1S/C22H24N2O3/c1-23-8-7-22-15-4-2-3-5-16(15)24-19(26)11-17-20(21(22)24)14(10-18(22)25)13(12-23)6-9-27-17/h2-6,14,17,20-21H,7-12H2,1H3/t14-,17-,20-,21-,22+/m0/s1
InChIKey RNZRHJNFQWMXHB-ZXXLSYNSSA-N
Formula C22H24N2O3
HBA 4
HBD 0
MW 364.45
Rotatable Bonds 0
TPSA 49.85
LogP 1.91
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 364.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos icaja Loganiaceae Plantae 1040889
2 Strychnos icaja Loganiaceae Plantae 1040889

Showing of synonyms

  • Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
  • Frederich M, Hayette MP, et al. (1999). In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum.. Antimicrobial agents and chemotherapy,1999, 43(9), 2328-31. [View] [PubMed]
CPRiL: 245484
Structure

SMILES: c1cccc(c1C234)N5C2C6C(CC3=O)C(CNCC4)=CCOC6CC5=O

Level: 0

Mol. Weight: 364.45 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
52.89
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
12.08
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.79
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.36
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
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
-14.28
Rat (Acute)
4.2
Rat (Chronic Oral)
1.7
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
492.63
Hydration Free Energy
-6.08
Log(D) at pH=7.4
0.92
Log(P)
1.16
Log S
-3.39
Log(Vapor Pressure)
-10.21
Melting Point
256.91
pKa Acid
7.49
pKa Basic
5.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.8817
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8732
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7821
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7435
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7410
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7058
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7014

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