N,N-dimethyl-5-(methylthio)varacin

ID: ALA222470

PubChem CID: 10319580

Max Phase: Preclinical

Molecular Formula: C13H19NO2S6

Molecular Weight: 413.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(OC)c2c(c(CCN(C)C)c1SC)SSSSS2

Standard InChI:  InChI=1S/C13H19NO2S6/c1-14(2)7-6-8-11(17-5)9(15-3)10(16-4)13-12(8)18-20-22-21-19-13/h6-7H2,1-5H3

Standard InChI Key:  IEMAUJASUZILRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.8027  -21.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016  -22.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164  -23.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146  -21.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300  -21.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289  -22.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8486  -23.1025    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729  -21.3008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6470  -21.5059    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9832  -22.2710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6237  -22.9512    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121  -20.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882  -21.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0868  -23.0351    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726  -22.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3738  -21.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254  -20.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179  -23.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042  -24.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057  -25.0999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920  -25.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210  -25.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  7  1  0
  8  9  1  0
  2  3  1  0
  4 12  1  0
  3  6  2  0
  1 13  1  0
  1  2  2  0
  2 14  1  0
  5  4  2  0
 14 15  1  0
  4  1  1  0
 13 16  1  0
 12 17  1  0
  5  6  1  0
  3 18  1  0
  6  7  1  0
 18 19  1  0
  5  8  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
 10 11  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA222470

   2-(6,7-dimethoxy-8-methylsulfanyl-1,2,3,4,5-benzopentathiepin-9-yl)-N,N-dimethylethanamine

Molecule Features

Natural Product: Yes

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: 413.70

Molecular Weight (Monoisotopic): 412.9740

AlogP: 5.59

#Rotatable Bonds: 6

Polar Surface Area: 21.70

Molecular Species: BASE

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.73

CX LogP: 4.93

CX LogD: 3.58

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: 1.04

References

1. Nakazawa T, Xu J, Nishikawa T, Oda T, Fujita A, Ukai K, Mangindaan RE, Rotinsulu H, Kobayashi H, Namikoshi M..  (2007)  Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium.,  70  (3): [PMID:17269824] [10.1021/np060593c]

2. Davison EK, Sperry J..  (2017)  Natural Products with Heteroatom-Rich Ring Systems.,  80  (11): [PMID:29135244] [10.1021/acs.jnatprod.7b00575]

Source

Source(1):

• Scientific Literature