(20S,24R)-Epoxy-dammarane-3beta,12beta,25-triol

ID: ALA2426036

Chembl Id: CHEMBL2426036

Cas Number: 162062-88-6

PubChem CID: 73352321

Max Phase: Preclinical

Molecular Formula: C30H52O4

Molecular Weight: 476.74

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)(O)[C@H]1CC[C@@](C)([C@H]2CC[C@]3(C)[C@@H]2[C@H](O)C[C@@H]2[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC[C@]23C)O1

Standard InChI:  InChI=1S/C30H52O4/c1-25(2)20-10-15-28(6)21(27(20,5)13-11-22(25)32)17-19(31)24-18(9-14-29(24,28)7)30(8)16-12-23(34-30)26(3,4)33/h18-24,31-33H,9-17H2,1-8H3/t18-,19+,20-,21+,22-,23+,24-,27-,28+,29+,30-/m0/s1

Standard InChI Key:  DOAJFZJEGHSYOI-LEJKDQSTSA-N

Alternative Forms

  1. Parent:

    ALA2426036

    Pixinol

Associated Targets(Human)

Liver microsome (8277 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatocyte (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CKM Tbio Creatine kinase M (67 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 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: 476.74Molecular Weight (Monoisotopic): 476.3866AlogP: 5.71#Rotatable Bonds: 2
Polar Surface Area: 69.92Molecular Species: NEUTRALHBA: 4HBD: 3
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 4.55CX LogD: 4.55
Aromatic Rings: Heavy Atoms: 34QED Weighted: 0.48Np Likeness Score: 3.18

References

1. Zhou Z, Ma C, Zhang H, Bi Y, Chen X, Tian H, Xie X, Meng Q, Lewis PJ, Xu J..  (2013)  Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents.,  68  [PMID:23994872] [10.1016/j.ejmech.2013.07.041]
2. Li L, Chen X, Li D, Zhong D..  (2011)  Identification of 20(S)-protopanaxadiol metabolites in human liver microsomes and human hepatocytes.,  39  (3): [PMID:21139039] [10.1124/dmd.110.036723]
3. Ren Q, Yang G, Guo M, Guo J, Li Y, Lu J, Yang Q, Tang H, Li Y, Fang X, Sun Y, Qi JG, Tian J, Wang H..  (2019)  Design, synthesis, and discovery of ocotillol-type amide derivatives as orally available modulators of P-glycoprotein-mediated multidrug resistance.,  161  [PMID:30347326] [10.1016/j.ejmech.2018.10.038]
4. Sun Y, Fang X, Gao M, Wang C, Gao H, Bi W, Tang H, Cui Y, Zhang L, Fan H, Yu H, Yang G..  (2020)  Synthesis and Structure-Activity Relationship of Pyxinol Derivatives as Novel Anti-Inflammatory Agents.,  11  (4): [PMID:32292550] [10.1021/acsmedchemlett.9b00562]
5. Cheng Y,Li R,Lin Z,Chen F,Dai J,Zhu Z,Chen L,Zhao Y.  (2020)  Structure-activity relationship analysis of dammarane-type natural products as muscle-type creatine kinase activators.,  30  (17.0): [PMID:32738969] [10.1016/j.bmcl.2020.127364]
6. Wang C,Gao M,Liu S,Zou Z,Ren R,Zhang C,Xie H,Sun J,Qi Y,Qu Q,Song Z,Yang G,Wang H.  (2021)  Pyxinol bearing amino acid residues: Easily achievable and promising modulators of P-glycoprotein-mediated multidrug resistance.,  216  [PMID:33706147] [10.1016/j.ejmech.2021.113317]
7. Yang G,Gao M,Sun Y,Wang C,Fang X,Gao H,Diao W,Yu H.  (2020)  Design, synthesis and anti-inflammatory activity of 3-amino acid derivatives of ocotillol-type sapogenins.,  202  [PMID:32650181] [10.1016/j.ejmech.2020.112507]

Source