flustramine T; 2-(6-bromo-2-((4aS*,4bR*,9bS*,10R*,10aR*)-7-bromo-1,1,3,13,13-pentamethyl-1,2,4a,5,10,10a-hexahydro-4b,9b-(epiminoethano)indeno[1,2-b]indol-10-yl)-1H-indol-3-yl)-N,N-dimethylethanamine

ID: ALA4792556

PubChem CID: 162671478

Max Phase: Preclinical

Molecular Formula: C34H43Br2N4+

Molecular Weight: 667.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C[C@H]2[C@@H]([C@@H](c3[nH]c4cc(Br)ccc4c3CCN(C)C)[C@]34CC[N+](C)(C)[C@]23Nc2cc(Br)ccc24)C(C)(C)C1

Standard InChI:  InChI=1S/C34H43Br2N4/c1-20-16-26-29(32(2,3)19-20)30(31-24(12-14-39(4)5)23-10-8-21(35)17-27(23)37-31)33-13-15-40(6,7)34(26,33)38-28-18-22(36)9-11-25(28)33/h8-11,16-18,26,29-30,37-38H,12-15,19H2,1-7H3/q+1/t26-,29-,30-,33+,34+/m0/s1

Standard InChI Key:  PTEVLAWJLRLDHG-DYSBYRCCSA-N

Molfile:  

 
     RDKit          2D

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   29.5172  -23.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2601  -25.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2590  -26.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9712  -26.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9694  -25.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6863  -25.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6911  -26.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4837  -26.5302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9678  -25.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4759  -25.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5427  -26.6884    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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   27.8669  -22.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2280  -22.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7945  -25.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0668  -26.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2846  -26.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5589  -26.9135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2751  -25.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0599  -25.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6712  -24.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4947  -24.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.0757  -27.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.6862  -27.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8589  -28.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6469  -28.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2535  -28.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8276  -29.7430    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   32.1074  -23.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4725  -24.9532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   31.5155  -25.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8828  -25.4237    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 24 40  1  1
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 27 42  1  1
M  CHG  1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA4792556

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 667.55

Molecular Weight (Monoisotopic): 665.1849

AlogP: 8.04

#Rotatable Bonds: 4

Polar Surface Area: 31.06

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.57

CX Basic pKa: 9.51

CX LogP: 3.15

CX LogD: 1.05

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: 1.15

References

1. Di X,Wang S,Oskarsson JT,Rouger C,Tasdemir D,Hardardottir I,Freysdottir J,Wang X,Molinski TF,Omarsdottir S.  (2020)  Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea.,  83  (10): [PMID:33016699] [10.1021/acs.jnatprod.0c00126]

Source

Source(1):

• Scientific Literature