Citrinamine B

ID: ALA5199839

PubChem CID: 168291012

Max Phase: Preclinical

Molecular Formula: C24H27Br2N11O5S

Molecular Weight: 741.43

Names and Identifiers

Canonical SMILES:  N=C1N=C(NCCS(=O)(=O)O)C(/C=C/CNC(=O)c2cc(Br)c[nH]2)(c2nc(N)[nH]c2/C=C/CNC(=O)c2cc(Br)c[nH]2)N1

Standard InChI:  InChI=1S/C24H27Br2N11O5S/c25-13-9-16(32-11-13)19(38)29-5-1-3-15-18(35-22(27)34-15)24(4-2-6-30-20(39)17-10-14(26)12-33-17)21(36-23(28)37-24)31-7-8-43(40,41)42/h1-4,9-12,32-33H,5-8H2,(H,29,38)(H,30,39)(H3,27,34,35)(H,40,41,42)(H3,28,31,36,37)/b3-1+,4-2+

Standard InChI Key:  UJQWOJQQUJKVEY-ZPUQHVIOSA-N

Molfile:  

 
     RDKit          2D

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   -3.4504   -1.2924    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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    0.9318    2.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1065    2.4007    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5701   -0.8856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3711   -2.9438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5905   -2.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -1.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158   -2.4010    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  4  5  2  0
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 32 33  2  0
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 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 39 37  1  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 37  2  0
 41 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5199839

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 741.43

Molecular Weight (Monoisotopic): 739.0284

AlogP: 1.21

#Rotatable Bonds: 12

Polar Surface Area: 259.12

Molecular Species: ZWITTERION

HBA: 8

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -1.44

CX Basic pKa: 9.75

CX LogP: -0.40

CX LogD: -0.54

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.09

Np Likeness Score: 0.41

References

1. Freire VF, Gubiani JR, Spencer TM, Hajdu E, Ferreira AG, Ferreira DAS, de Castro Levatti EV, Burdette JE, Camargo CH, Tempone AG, Berlinck RGS..  (2022)  Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar.,  85  (5.0): [PMID:35427139] [10.1021/acs.jnatprod.2c00094]

Source

Source(1):

• Scientific Literature