gamma-rubromycin

ID: ALA3347482

PubChem CID: 137321735

Max Phase: Preclinical

Molecular Formula: C26H18O12

Molecular Weight: 522.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc2cc3c(c(O)c2c(=O)o1)O[C@]1(CC3)Cc2c(O)c3c(c(O)c2O1)C(=O)C(OC)=CC3=O

Standard InChI:  InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1

Standard InChI Key:  CKLKRRFSZZUFKT-SANMLTNESA-N

Molfile:  

     RDKit          2D

 38 43  0  0  0  0  0  0  0  0999 V2000
    6.9099  -10.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1353   -8.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9642   -8.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3457   -9.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1621   -9.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6030   -8.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2215   -8.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989   -7.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0147   -7.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7477   -7.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4273   -8.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8095   -9.4988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8695   -8.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6938   -8.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0862  -10.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030   -9.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8887   -9.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4515   -9.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8347  -10.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6552  -10.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194   -9.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182  -10.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331  -10.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -9.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -8.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965   -9.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   -8.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329  -11.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7467   -9.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7456  -10.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585  -10.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -9.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -8.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4563  -11.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785   -9.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793  -10.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652  -10.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639   -9.3304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  2  0
  1  4  1  0
  3  2  1  0
  2 16  2  0
  3  4  2  0
  3  8  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 30  1  0
 29 24  1  0
 24 21  1  0
 24 25  2  0
 21 26  1  0
 26 27  1  0
 23 28  2  0
 29 30  2  0
 29 32  1  0
 30 31  1  0
 31 36  2  0
 35 32  2  0
 32 33  1  0
 31 34  1  0
 35 36  1  0
 36 37  1  0
 37 18  1  0
 18 38  1  1
 38 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3347482

   ---

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: 522.42

Molecular Weight (Monoisotopic): 522.0798

AlogP: 2.26

#Rotatable Bonds: 2

Polar Surface Area: 179.03

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.59

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.30

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: 1.52

References

1. Chen JL, Sperry J, Ip NY, Brimble MA.  (2011)  Natural products targeting telomere maintenance,  2  (4): [10.1039/C0MD00241K]

2. Wang X, Elshahawi SI, Ponomareva LV, Ye Q, Liu Y, Copley GC, Hower JC, Hatcher BE, Kharel MK, Van Lanen SG, She QB, Voss SR, Thorson JS, Shaaban KA..  (2019)  Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces.,  82  (12): [PMID:31833370] [10.1021/acs.jnatprod.9b01015]

Source

Source(1):

• Scientific Literature