Fredericamycin A

ID: ALA256952

Chembl Id: CHEMBL256952

PubChem CID: 135427349

Max Phase: Preclinical

Molecular Formula: C30H21NO9

Molecular Weight: 539.50

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  C/C=C/C=C/c1cc2cc3c(c(O)c2c(=O)[nH]1)[C@@]1(CC3)C(=O)c2c(O)c3c(c(O)c2C1=O)C(=O)C(OC)=CC3=O

Standard InChI:  InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,34-36H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+/t30-/m0/s1

Standard InChI Key:  BZONSJUONOFNNP-MHSJTTIKSA-N

Alternative Forms

  1. Parent:

    ALA256952

    FDM A

Associated Targets(Human)

Panel (12 tumour cell lines) (42 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 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

Calculated Properties

Molecular Weight: 539.50Molecular Weight (Monoisotopic): 539.1216AlogP: 3.41#Rotatable Bonds: 3
Polar Surface Area: 171.06Molecular Species: NEUTRALHBA: 9HBD: 4
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: 7.03CX Basic pKa: CX LogP: 5.78CX LogD: 5.14
Aromatic Rings: 3Heavy Atoms: 40QED Weighted: 0.22Np Likeness Score: 1.87

References

1. Abel U, Simon W, Eckard P, Hansske FG..  (2006)  Design and semisynthesis of novel fredericamycin A derivatives with an improved antitumor profile.,  16  (12): [PMID:16621542] [10.1016/j.bmcl.2006.03.029]
2. Chen Y, Luo Y, Ju J, Wendt-Pienkowski E, Rajski SR, Shen B..  (2008)  Identification of fredericamycin E from Streptomyces griseus: Insights into fredericamycin A biosynthesis highlighting carbaspirocycle formation.,  71  (3): [PMID:18232659] [10.1021/np070664n]

Source