Rubrumazine C

ID: ALA3577257

PubChem CID: 122177585

Max Phase: Preclinical

Molecular Formula: C24H33N3O4

Molecular Weight: 427.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)c1[nH]c2c(C[C@H](O)C(C)(C)O)cccc2c1C[C@@H]1NC(=O)[C@H](C)NC1=O

Standard InChI:  InChI=1S/C24H33N3O4/c1-7-23(3,4)20-16(12-17-22(30)25-13(2)21(29)26-17)15-10-8-9-14(19(15)27-20)11-18(28)24(5,6)31/h7-10,13,17-18,27-28,31H,1,11-12H2,2-6H3,(H,25,30)(H,26,29)/t13-,17-,18-/m0/s1

Standard InChI Key:  PCQRMVOVGYONSH-KKXDTOCCSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6987   -0.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2871    0.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    3.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -5.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6449    6.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    2.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3352   -3.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175    7.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6468    5.1720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    5.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826   -6.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    6.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878   -5.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0235    1.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868    3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2887    4.5530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -5.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18  6  1  0
 22 29  1  0
 19 10  1  0
 25  8  1  0
 20 11  1  0
 29 28  1  0
 22 24  1  1
  1 16  1  0
 26 25  1  0
  7 28  1  0
 28 12  2  0
 25 31  1  0
 11  2  1  0
 16 18  2  0
 20 19  2  0
 17 26  1  0
  7 10  1  1
 11  5  1  0
  7 21  1  0
  6 30  2  0
  5 27  2  0
 21  9  1  0
 30  4  1  0
  4 20  1  0
 19 15  1  0
  9 14  2  0
 15  1  2  0
  6 17  1  0
 25 23  1  0
 26 13  1  1
 15 30  1  0
 11  3  1  0
  9 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577257

   ---

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: 427.55

Molecular Weight (Monoisotopic): 427.2471

AlogP: 1.85

#Rotatable Bonds: 7

Polar Surface Area: 114.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.04

CX Basic pKa: ┄

CX LogP: 1.88

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: 2.05

References

1. Meng LH, Du FY, Li XM, Pedpradab P, Xu GM, Wang BG..  (2015)  Rubrumazines A-C, Indolediketopiperazines of the Isoechinulin Class from Eurotium rubrum MA-150, a Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.,  78  (4): [PMID:25730346] [10.1021/np5007839]

Source

Source(1):

• Scientific Literature