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Icajine
- 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
Icajine
5525-31-5
16,19-Secostrychnidine-10,16-dione, 19-methyl-
CHEBI:132668
19-methyl-16,19-seco-strychnidine-10,16-dione
(1S,10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
(4aR,6aS,12aS,12bR,12cS)-15-methyl-4a,5,12,12a,12b,12c-hexahydro-11H-6a,4-(ethanoiminomethano)-1-oxa-10b-azacyclohepta[1,2,3-cd]fluoranthene-6,11(2H)-dione
(1S,10S,22R,23R,24S)-4-methyl-9-oxa-4,13-diazahexacyclo(11.6.5.01,24.06,22.010,23.014,19)tetracosa-6,14,16,18-tetraene-12,20-dione
(4aR,6aS,12aS,12bR,12cS)-15-methyl-4a,5,12,12a,12b,12c-hexahydro-11H-6a,4-(ethanoiminomethano)-1-oxa-10b-azacyclohepta(1,2,3-cd)fluoranthene-6,11(2H)-dione
4-methyl-9-oxa-4,13-diazahexacyclo(11.6.5.01,24.06,22.010,23.014,19)tetracosa-6,14,16,18-tetraene-12,20-dione
4-methyl-9-oxa-4,13-diazahexacyclo[11.6.5.01,24.06,22.010,23.014,19]tetracosa-6,14,16,18-tetraene-12,20-dione
Rnzrhjnfqwmxhb-uhfffaoysa-n
Strychnidinium, 16-hydroxy-19-methyl-
N-Methylpseudostrychnine
SCHEMBL1445138
CHEMBL2164624
- 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]
Pubchem:
3083907
Cas:
5525-31-5
Gnps:
CCMSLIB00004679998
Zinc:
ZINC000001716562
Chebi:
132668
Metabolights:
MTBLC132668
Chembl:
CHEMBL2164624
CPRiL:
245484
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 |