CRYPTOLEPINE HYDROCHLORIDE

ID: ALA92129

Max Phase: Preclinical

Molecular Formula: C16H13ClN2

Molecular Weight: 232.29

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (2): Cryptolepine | Cryptolepine HCl
Synonyms from Alternative Forms(2):

    Canonical SMILES:  C[n+]1c2ccccc2cc2[n-]c3ccccc3c21.Cl

    Standard InChI:  InChI=1S/C16H12N2.ClH/c1-18-15-9-5-2-6-11(15)10-14-16(18)12-7-3-4-8-13(12)17-14;/h2-10H,1H3;1H

    Standard InChI Key:  PACBZNVVTJRUCN-UHFFFAOYSA-N

    Associated Targets(Human)

    RT-112 346 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    NCI-H460 60772 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    BE 127 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Quinone reductase 1 1746 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HUVEC 11049 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MAP kinase p38 1586 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Nuclear factor NF-kappa-B p65 subunit 627 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SK-N-SH 1499 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    3T3-L1 3664 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mus musculus 284745 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasmodium falciparum 966862 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    MAC15A 81 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    RAW 181 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasmodium yoelii 6656 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Plasmodium berghei 192651 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma brucei rhodesiense 7991 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma cruzi 99888 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Leishmania donovani 89745 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    L6 7924 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histidine-rich protein 528 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Saccharomyces cerevisiae 19171 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    M109 194 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vero 26788 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rhodesain 1463 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cathepsin B-like cysteine protease 88 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Trypanosoma brucei brucei 13300 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: NoOral: NoChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: NoAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 232.29Molecular Weight (Monoisotopic): 232.1000AlogP: 2.93#Rotatable Bonds: 0
    Polar Surface Area: 17.98Molecular Species: NEUTRALHBA: 0HBD: 0
    #RO5 Violations: 0HBA (Lipinski): 2HBD (Lipinski): 0#RO5 Violations (Lipinski): 0
    CX Acidic pKa: 9.16CX Basic pKa: CX LogP: -1.02CX LogD: -1.03
    Aromatic Rings: 4Heavy Atoms: 18QED Weighted: 0.43Np Likeness Score: 0.34

    References

    1. Bierer DE, Dubenko LG, Zhang P, Lu Q, Imbach PA, Garofalo AW, Phuan PW, Fort DM, Litvak J, Gerber RE, Sloan B, Luo J, Cooper R, Reaven GM..  (1998)  Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure isolated from Cryptolepis sanguinolenta.,  41  (15): [PMID:9667966] [10.1021/jm970735n]
    2. Bierer DE, Fort DM, Mendez CD, Luo J, Imbach PA, Dubenko LG, Jolad SD, Gerber RE, Litvak J, Lu Q, Zhang P, Reed MJ, Waldeck N, Bruening RC, Noamesi BK, Hector RF, Carlson TJ, King SR..  (1998)  Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine: its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities.,  41  (6): [PMID:9526563] [10.1021/jm9704816]
    3. Arzel E, Rocca P, Grellier P, Labaeïd M, Frappier F, Guéritte F, Gaspard C, Marsais F, Godard A, Quéguiner G..  (2001)  New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: in vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines.,  44  (6): [PMID:11300877] [10.1021/jm0010419]
    4. Onyeibor O, Croft SL, Dodson HI, Feiz-Haddad M, Kendrick H, Millington NJ, Parapini S, Phillips RM, Seville S, Shnyder SD, Taramelli D, Wright CW..  (2005)  Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities, and consideration of their antimalarial mode of action.,  48  (7): [PMID:15801861] [10.1021/jm040893w]
    5. Olajide OA, Heiss EH, Schachner D, Wright CW, Vollmar AM, Dirsch VM..  (2007)  Synthetic cryptolepine inhibits DNA binding of NF-kappaB.,  15  (1): [PMID:17064915] [10.1016/j.bmc.2006.10.018]
    6. Seville S, Phillips RM, Shnyder SD, Wright CW..  (2007)  Synthesis of cryptolepine analogues as potential bioreducible anticancer agents.,  15  (19): [PMID:17643990] [10.1016/j.bmc.2007.06.062]
    7. Lavrado J, Paulo A, Gut J, Rosenthal PJ, Moreira R..  (2008)  Cryptolepine analogues containing basic aminoalkyl side-chains at C-11: synthesis, antiplasmodial activity, and cytotoxicity.,  18  (4): [PMID:18207399] [10.1016/j.bmcl.2008.01.015]
    8. Cimanga K, De Bruyne T, Pieters L, Vlietinck AJ, Turger CA..  (1997)  In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta.,  60  (7): [PMID:9249972] [10.1021/np9605246]
    9. Yang SW, Abdel-Kader M, Malone S, Werkhoven MC, Wisse JH, Bursuker I, Neddermann K, Fairchild C, Raventos-Suarez C, Menendez AT, Lane K, Kingston DG..  (1999)  Synthesis and biological evaluation of analogues of cryptolepine, an alkaloid isolated from the Suriname rainforest.,  62  (7): [PMID:10425120] [10.1021/np990035g]
    10. Acharya BN, Saraswat D, Kaushik MP..  (2008)  Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway.,  43  (12): [PMID:18395298] [10.1016/j.ejmech.2008.02.005]
    11. Van Miert S, Hostyn S, Maes BU, Cimanga K, Brun R, Kaiser M, Mátyus P, Dommisse R, Lemière G, Vlietinck A, Pieters L..  (2005)  Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound.,  68  (5): [PMID:15921407] [10.1021/np0496284]
    12. Van Baelen G, Hostyn S, Dhooghe L, Tapolcsányi P, Mátyus P, Lemière G, Dommisse R, Kaiser M, Brun R, Cos P, Maes L, Hajós G, Riedl Z, Nagy I, Maes BU, Pieters L..  (2009)  Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.,  17  (20): [PMID:19781948] [10.1016/j.bmc.2009.08.057]
    13. Bonazzi S, Barbaras D, Patiny L, Scopelliti R, Schneider P, Cole ST, Kaiser M, Brun R, Gademann K..  (2010)  Antimalarial and antitubercular nostocarboline and eudistomin derivatives: synthesis, in vitro and in vivo biological evaluation.,  18  (4): [PMID:20133138] [10.1016/j.bmc.2010.01.013]
    14. Rojas M, Wright CW, Piña B, Portugal J..  (2008)  Genomewide expression profiling of cryptolepine-induced toxicity in Saccharomyces cerevisiae.,  52  (11): [PMID:18710911] [10.1128/aac.00532-08]
    15. Lavrado J, Cabal GG, Prudêncio M, Mota MM, Gut J, Rosenthal PJ, Díaz C, Guedes RC, dos Santos DJ, Bichenkova E, Douglas KT, Moreira R, Paulo A..  (2011)  Incorporation of basic side chains into cryptolepine scaffold: structure-antimalarial activity relationships and mechanistic studies.,  54  (3): [PMID:21207937] [10.1021/jm101383f]
    16. Lavrado J, Mackey Z, Hansell E, McKerrow JH, Paulo A, Moreira R..  (2012)  Antitrypanosomal and cysteine protease inhibitory activities of alkyldiamine cryptolepine derivatives.,  22  (19): [PMID:22926067] [10.1016/j.bmcl.2012.07.104]
    17. Olajide OA, Bhatia HS, de Oliveira AC, Wright CW, Fiebich BL..  (2013)  Anti-neuroinflammatory properties of synthetic cryptolepine in human neuroblastoma cells: possible involvement of NF-κB and p38 MAPK inhibition.,  63  [PMID:23507189] [10.1016/j.ejmech.2013.02.004]
    18. Chadha N, Silakari O..  (2017)  Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.,  134  [PMID:28412530] [10.1016/j.ejmech.2017.04.003]

    Source