5-Bromo-thiophene-2-carboxylic acid (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester

ID: ALA4852095

PubChem CID: 164615662

Max Phase: Preclinical

Molecular Formula: C27H23BrO9S

Molecular Weight: 603.44

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@H](OC(=O)c3ccc(Br)s3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C27H23BrO9S/c1-31-18-6-12(7-19(32-2)25(18)33-3)22-13-8-16-17(36-11-35-16)9-14(13)24(15-10-34-27(30)23(15)22)37-26(29)20-4-5-21(28)38-20/h4-9,15,22-24H,10-11H2,1-3H3/t15-,22+,23-,24-/m0/s1

Standard InChI Key:  UEGSPDFTPUXPLI-LXFAFOKJSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   38.1446   -6.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1428   -5.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8582   -5.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8570   -6.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5738   -6.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5761   -5.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4299   -6.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4312   -5.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6433   -5.4861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1550   -6.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6413   -6.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2975   -5.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2942   -6.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0836   -6.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5748   -6.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0889   -5.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3354   -7.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5762   -4.4988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8618   -4.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5727   -7.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8587   -8.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8574   -9.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5718   -9.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2890   -9.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2868   -8.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5719  -10.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8576  -10.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0044   -9.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0063  -10.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1423   -9.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4286   -9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5071   -4.9410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   40.5029   -7.3699    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.1474   -4.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8618   -3.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5293   -2.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2745   -1.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4495   -1.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1947   -2.7773    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.9646   -1.3255    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  4  2  0
  3  2  2  0
  2  8  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5 13  1  0
 12  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 16  1  0
 14 17  2  0
  6 18  1  6
 18 19  1  0
  5 20  1  6
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 26 27  1  0
 24 28  1  0
 28 29  1  0
 22 30  1  0
 30 31  1  0
 12 32  1  6
 13 33  1  1
 19 34  2  0
 19 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 35  1  0
 38 40  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4852095

    ---

Associated Targets(Human)

PC-3M (435 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMEC (560 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: 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: 603.44Molecular Weight (Monoisotopic): 602.0246AlogP: 5.10#Rotatable Bonds: 6
Polar Surface Area: 98.75Molecular Species: NEUTRALHBA: 10HBD:
#RO5 Violations: 2HBA (Lipinski): 9HBD (Lipinski): #RO5 Violations (Lipinski): 2
CX Acidic pKa: CX Basic pKa: CX LogP: 4.97CX LogD: 4.97
Aromatic Rings: 3Heavy Atoms: 38QED Weighted: 0.36Np Likeness Score: 0.80

References

1. Zhao Y, Li D, Wei M, Du R, Yan Z..  (2021)  The ester derivatives obtained by C-ring modification of podophyllotoxin induce apoptosis and inhibited proliferation in PC-3M cells via down-regulation of PI3K/Akt signaling pathway.,  46  [PMID:34098082] [10.1016/j.bmcl.2021.128174]

Source