Hippuristanol

ID: ALA1098427

Chembl Id: CHEMBL1098427

Cas Number: 80442-78-0

PubChem CID: 9981822

Max Phase: Preclinical

Molecular Formula: C28H46O5

Molecular Weight: 462.67

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Hippuristanol | Hippuristanol|Desacetoxyhippurin 1|80442-78-0|(1S,2S,3'S,4S,6R,7R,8R,9S,11S,12S,13S,16R,18S)-2',2',3',7,9,13-hexamethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,5'-oxolane]-7,11,16-triol|45PK2NS4NQ|SCHEMBL1374807|CHEMBL1098427|DTXSID50433627|HPHXKNOXVBFETI-SHCCRYCOSA-N|BDBM50235738|AKOS027323973|Q10861089|Furostan-3,11,20-triol, 22,25-epoxy-24-methyl-, (3alpha,5alpha,11beta,22beta,24S)-|(1'S,2R,2'S,4S,4'S,7'R,8'R,9'S,11'S,12'S,13'S,16'R,18'S)-4,5,5,7',9',13'-hexametShow More

Canonical SMILES:  C[C@H]1C[C@@]2(O[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@H](O)CC[C@]6(C)[C@H]5[C@@H](O)C[C@]4(C)[C@H]3[C@@]2(C)O)OC1(C)C

Standard InChI:  InChI=1S/C28H46O5/c1-15-13-28(33-24(15,2)3)27(6,31)23-21(32-28)12-19-18-8-7-16-11-17(29)9-10-25(16,4)22(18)20(30)14-26(19,23)5/h15-23,29-31H,7-14H2,1-6H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-,25-,26-,27+,28+/m0/s1

Standard InChI Key:  HPHXKNOXVBFETI-SHCCRYCOSA-N

Alternative Forms

  1. Parent:

    ALA1098427

    HIPPURISTANOL

Associated Targets(Human)

HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4A1 Tchem Eukaryotic initiation factor 4A-I (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4E Tchem Eukaryotic translation initation factor (600 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4B Tbio Eukaryotic translation initiation factor 4B (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4A3 Tchem Eukaryotic initiation factor 4A-III (131 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4A2 Tbio Eukaryotic initiation factor 4A-II (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHX29 Tbio ATP-dependent RNA helicase DHX29 (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNRNP200 Tchem U5 small nuclear ribonucleoprotein 200 kDa helicase (313 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Internal ribosome entry site (IRES) (199 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Eif4a1 Eukaryotic initiation factor 4A-I (29 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Eukaryotic initiation factor 4A (1 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EIF4A1 Eukaryotic initiation factor 4A-I (8 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Triticum aestivum (1582 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

Calculated Properties

Molecular Weight: 462.67Molecular Weight (Monoisotopic): 462.3345AlogP: 4.27#Rotatable Bonds:
Polar Surface Area: 79.15Molecular Species: NEUTRALHBA: 5HBD: 3
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 12.86CX Basic pKa: CX LogP: 3.27CX LogD: 3.27
Aromatic Rings: Heavy Atoms: 33QED Weighted: 0.50Np Likeness Score: 3.19

References

1. Li W, Dang Y, Liu JO, Yu B..  (2010)  Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity.,  20  (10): [PMID:20409710] [10.1016/j.bmcl.2010.03.093]
2. Bordeleau ME, Mori A, Oberer M, Lindqvist L, Chard LS, Higa T, Belsham GJ, Wagner G, Tanaka J, Pelletier J..  (2006)  Functional characterization of IRESes by an inhibitor of the RNA helicase eIF4A.,  (4): [PMID:16532013] [10.1038/nchembio776]
3. Somaiah R, Ravindar K, Cencic R, Pelletier J, Deslongchamps P..  (2014)  Synthesis of the antiproliferative agent hippuristanol and its analogues from hydrocortisone via Hg(II)-catalyzed spiroketalization: structure-activity relationship.,  57  (6): [PMID:24588834] [10.1021/jm401799j]
4. Ito M, Iwatani M, Kamada Y, Sogabe S, Nakao S, Tanaka T, Kawamoto T, Aparicio S, Nakanishi A, Imaeda Y..  (2017)  Discovery of selective ATP-competitive eIF4A3 inhibitors.,  25  (7): [PMID:28283335] [10.1016/j.bmc.2017.02.035]
5. Tillotson J, Kedzior M, Guimarães L, Ross AB, Peters TL, Ambrose AJ, Schmidlin CJ, Zhang DD, Costa-Lotufo LV, Rodríguez AD, Schatz JH, Chapman E..  (2017)  ATP-competitive, marine derived natural products that target the DEAD box helicase, eIF4A.,  27  (17): [PMID:28757063] [10.1016/j.bmcl.2017.07.045]
6. Ito M, Tanaka T, Cary DR, Iwatani-Yoshihara M, Kamada Y, Kawamoto T, Aparicio S, Nakanishi A, Imaeda Y..  (2017)  Discovery of Novel 1,4-Diacylpiperazines as Selective and Cell-Active eIF4A3 Inhibitors.,  60  (8): [PMID:28358513] [10.1021/acs.jmedchem.6b01904]
7. Ernst JT, Thompson PA, Nilewski C, Sprengeler PA, Sperry S, Packard G, Michels T, Xiang A, Tran C, Wegerski CJ, Eam B, Young NP, Fish S, Chen J, Howard H, Staunton J, Molter J, Clarine J, Nevarez A, Chiang GG, Appleman JR, Webster KR, Reich SH..  (2020)  Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase.,  63  (11): [PMID:32470302] [10.1021/acs.jmedchem.0c00182]
8. Fan A, Sharp PP..  (2021)  Inhibitors of Eukaryotic Translational Machinery as Therapeutic Agents.,  64  (5.0): [PMID:33592144] [10.1021/acs.jmedchem.0c01746]

Source