(6aR,9S)-7-methyl-9-phenyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline maleate

ID: ALA3245291

PubChem CID: 90672171

Max Phase: Preclinical

Molecular Formula: C25H24N2O4

Molecular Weight: 300.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@H](c2ccccc2)C=C2c3cccc4[nH]cc(c34)C[C@H]21.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C21H20N2.C4H4O4/c1-23-13-16(14-6-3-2-4-7-14)10-18-17-8-5-9-19-21(17)15(12-22-19)11-20(18)23;5-3(6)1-2-4(7)8/h2-10,12,16,20,22H,11,13H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t16-,20-;/m1./s1

Standard InChI Key:  QHVLEEQTUJJDTQ-PIGXHTMWSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   10.5283   -8.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1186   -8.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2990   -8.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892   -8.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1186   -7.4462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0697   -8.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2990   -7.4462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743   -8.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -9.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9325  -10.5418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7521  -10.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8159   -8.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5276   -8.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268   -7.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8079   -6.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -7.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2363   -8.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056   -6.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5210   -8.9313    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5105   -5.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903   -4.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957   -5.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7992   -4.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5069   -4.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  4  7  2  0
  4  8  1  0
  9 10  2  0
 10 12  1  0
 16 11  2  0
 11  9  1  0
 18 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 16 18  1  0
 16 19  1  0
 15 17  1  0
 17 20  1  0
 15 18  1  0
 19 20  1  0
 19 24  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 23 26  1  1
 20 27  1  1
 26 28  2  0
 28 32  1  0
 31 29  1  0
 29 30  2  0
 30 26  1  0
 31 32  2  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 300.40

Molecular Weight (Monoisotopic): 300.1626

AlogP: 4.21

#Rotatable Bonds: 1

Polar Surface Area: 19.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.56

CX LogP: 4.05

CX LogD: 2.86

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.71

Np Likeness Score: 0.93

References

1. Bach NJ, Kornfeld EC, Dorman DE..  (1977)  Synthesis and biological activity of 8-arylergolines.,  20  (8): [PMID:561190] [10.1021/jm00218a025]

Source

Source(1):

• Scientific Literature