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(6aR,9R)-N-phenyl-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-7(4H)-carboxamide

ID: ALA1806523

PubChem CID: 56673431

Max Phase: Preclinical

Molecular Formula: C26H26N4O2

Molecular Weight: 426.52

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C([C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C(=O)Nc2ccccc2)C1)N1CCCC1

Standard InChI:  InChI=1S/C26H26N4O2/c31-25(29-11-4-5-12-29)18-13-21-20-9-6-10-22-24(20)17(15-27-22)14-23(21)30(16-18)26(32)28-19-7-2-1-3-8-19/h1-3,6-10,13,15,18,23,27H,4-5,11-12,14,16H2,(H,28,32)/t18-,23-/m1/s1

Standard InChI Key:  MSOSXJRGMKTMRH-WZONZLPQSA-N

Molfile:  

     RDKit          2D

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    8.7991  -14.2839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Associated Targets(Human)

CXCR3 Tchem C-X-C chemokine receptor type 3 (2736 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Serum (1292 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Cxcr3 C-X-C chemokine receptor type 3 (96 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cxcr3 C-X-C chemokine receptor type 3 (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Serum (604 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

Biocomponents

Calculated Properties

Molecular Weight: 426.52Molecular Weight (Monoisotopic): 426.2056AlogP: 4.26#Rotatable Bonds: 2
Polar Surface Area: 68.44Molecular Species: NEUTRALHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 13.36CX Basic pKa: CX LogP: 3.11CX LogD: 3.11
Aromatic Rings: 3Heavy Atoms: 32QED Weighted: 0.64Np Likeness Score: -0.23

References

1. Thoma G, Baenteli R, Lewis I, Jones D, Kovarik J, Streiff MB, Zerwes HG..  (2011)  Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood.,  21  (16): [PMID:21764306] [10.1016/j.bmcl.2011.06.070]
2. Ondeykal, John G JG and 17 more authors.  2005  Discovery of structurally diverse natural product antagonists of chemokine receptor CXCR3.  [PMID:15789559]
3. Watson, Robert J RJ and 13 more authors.  2008-01-01  Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives.  [PMID:18032038]
4. Knight, Roland L RL and 11 more authors.  2008-01-15  Development of CXCR3 antagonists. Part 4: discovery of 2-amino-(4-tropinyl)quinolines.  [PMID:18068363]
5. Hayes, Martin E ME and 8 more authors.  2008-04-01  Lead identification of 2-iminobenzimidazole antagonists of the chemokine receptor CXCR3.  [PMID:18337097]
6. Crosignani, Stefano S and 10 more authors.  2010-06-15  Discovery of a novel series of CXCR3 antagonists.  [PMID:20483605]

Source