ID: ALA1563246

Max Phase: Preclinical

Molecular Formula: C21H30O3

Molecular Weight: 330.47

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (1): RP-49356
Synonyms from Alternative Forms(1):

    Canonical SMILES:  CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@]12C

    Standard InChI:  InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18+,19+,20-,21+/m0/s1

    Standard InChI Key:  BFZHCUBIASXHPK-QJSKAATBSA-N

    Associated Targets(Human)

    Steroid 5-alpha-reductase 2 937 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Survival motor neuron protein 34246 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    ATPase family AAA domain-containing protein 5 122566 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Chromobox protein homolog 1 92434 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    UDP-glucuronosyltransferase 2B7 787 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Geminin 128009 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosyl-DNA phosphodiesterase 1 345557 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    11-beta-hydroxysteroid dehydrogenase 1 5910 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    11-beta-hydroxysteroid dehydrogenase 2 1168 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    DNA-(apurinic or apyrimidinic site) lyase 38016 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Progesterone receptor 8562 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone deacetylase 6 20808 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cavia porcellus 23802 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Androgen Receptor 5522 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-lactamase AmpC 62480 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Progesterone receptor 52 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Progesterone receptor 449 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SARS-CoV-2 38078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Replicase polyprotein 1ab 11336 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: 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: 330.47Molecular Weight (Monoisotopic): 330.2195AlogP: 3.69#Rotatable Bonds: 1
    Polar Surface Area: 54.37Molecular Species: NEUTRALHBA: 3HBD: 1
    #RO5 Violations: 0HBA (Lipinski): 3HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: CX LogP: 2.84CX LogD: 2.84
    Aromatic Rings: 0Heavy Atoms: 24QED Weighted: 0.80Np Likeness Score: 2.51

    References

    1. Koga H, Sato H, Ishizawa T, Kiyonori K, Hiroyuki N, Jun-ichi I, Yoshida S, Sugo I.  (1993)  N,N-disubstituted benzopyran-4-(N-cyano)carboxamidines, cromakalim analogs with selective activity for guinea pig trachealis,  (6): [10.1016/S0960-894X(00)80297-8]
    2. Koga H, Sato H, Ishizawa T, Kuromaru K, Makino T, Taka N, Takahashi T, Sato T, Nabata H.  (1993)  Benzopyran-4-carboxamide K+ channel openers,  (6): [10.1016/S0960-894X(00)80298-X]
    3. Ishizawa T, Koga H, Sato H, Makino T, Taka N, Takahashi T, Sato T, Hiroyuki N.  (1994)  Substituent effects of benzopyran-4-(N-cyano)-carboxamidine potassium channel openers for selectivity to guinea pig trachealis,  (16): [10.1016/S0960-894X(01)80551-5]
    4. Manley PW, Quast U, Andres H, Bray K..  (1993)  Synthesis of and radioligand binding studies with a tritiated pinacidil analogue: receptor interactions of structurally different classes of potassium channel openers and blockers.,  36  (14): [PMID:8336339] [10.1021/jm00066a009]
    5. Rasmusson GH, Reynolds GF, Steinberg NG, Walton E, Patel GF, Liang T, Cascieri MA, Cheung AH, Brooks JR, Berman C..  (1986)  Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.,  29  (11): [PMID:3783591] [10.1021/jm00161a028]
    6. Sato H, Koga H, Ishizawa T, Makino T, Taka N, Takahashi T, Nabata H.  (1995)  Vasorelaxant activity of 2-fluoroalkyl-6-nitro-2H-1-benzopyran-4-carbothioamide and -carboxamide K+ channel openers,  (3): [10.1016/0960-894X(95)00007-G]
    7. Sato H, Koga H, Ishizawa T, Makino T, Kuromaru K, Taka N, Takahashi T, Sato T, Nabata H.  (1993)  Vasorelaxant activity of 2-substituted 6-nitro-2H-1-benzopyran-4-carbothioamide K+ channel openers,  (12): [10.1016/S0960-894X(01)80729-0]
    8. Taka N, Koga H, Sato H, Ishizawa T, Takahashi T, Imagawa J.  (1994)  Vasorelaxant activity of 2-fluoromethylbenzopyran K+ channel openers,  (24): [10.1016/S0960-894X(01)80835-0]
    9. Koga H, Ohta M, Sato H, Ishizawa T, Hiroyuki N.  (1993)  Design of potent K+ channel openers by pharmacophore model,  (4): [10.1016/S0960-894X(01)81242-7]
    10. PubChem BioAssay data set, 
    11. PubChem BioAssay data set, 
    12. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]
    13. Pandya K, Dietrich D, Seibert J, Vederas JC, Odermatt A..  (2013)  Synthesis of sterically encumbered 11β-aminoprogesterone derivatives and evaluation as 11β-hydroxysteroid dehydrogenase inhibitors and mineralocorticoid receptor antagonists.,  21  (21): [PMID:24074876] [10.1016/j.bmc.2013.08.068]
    14. Lee DL, Kollman PA, Marsh FJ, Wolff ME..  (1977)  Quantitative relationships between steroid structure and binding to putative progesterone receptors.,  20  (9): [PMID:926114] [10.1021/jm00219a006]
    15. de Ravel MR, Alameh G, Melikian M, Mahiout Z, Emptoz-Bonneton A, Matera EL, Lomberget T, Barret R, Rocheblave L, Walchshofer N, Beltran S, El Jawad L, Mappus E, Grenot C, Pugeat M, Dumontet C, Le Borgne M, Cuilleron CY..  (2015)  Synthesis of new steroidal inhibitors of P-glycoprotein-mediated multidrug resistance and biological evaluation on K562/R7 erythroleukemia cells.,  58  (4): [PMID:25634041] [10.1021/jm501676v]
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    17. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
    18. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
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