Asperversiamide I

ID: ALA4525407

PubChem CID: 145721069

Max Phase: Preclinical

Molecular Formula: C26H31N3O5

Molecular Weight: 465.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@@]12Nc3cc4c(cc3[C@]1(O)C[C@]1(NC(=O)[C@H]3CCCN3C1=O)O2)C=CC(C)(C)O4

Standard InChI:  InChI=1S/C26H31N3O5/c1-6-22(2,3)26-24(32,14-25(34-26)21(31)29-11-7-8-18(29)20(30)28-25)16-12-15-9-10-23(4,5)33-19(15)13-17(16)27-26/h6,9-10,12-13,18,27,32H,1,7-8,11,14H2,2-5H3,(H,28,30)/t18-,24-,25+,26+/m1/s1

Standard InChI Key:  KQSNCKYUOHBTBD-UEEUSRRGSA-N

Molfile:  

 
     RDKit          2D

 35 40  0  0  0  0  0  0  0  0999 V2000
    7.2557   -5.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5499   -5.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2602   -6.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476   -6.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603   -5.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2428   -5.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773   -5.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -4.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693   -5.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -4.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7734   -4.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -4.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653   -5.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842   -4.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8890   -5.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -5.6491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6612   -4.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1481   -4.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9243   -4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9172   -3.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1366   -3.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9172   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6225   -4.3088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3278   -3.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2457   -3.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -6.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2083   -2.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0349   -4.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6225   -2.6744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3247   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9326   -2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6061   -1.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7964   -1.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304   -3.4916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5423   -7.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  9  7  1  0
  7 15  2  0
 14  8  2  0
  8 10  1  0
  9 10  2  0
  9 13  1  0
 10 11  1  0
 11 12  2  0
 12  5  1  0
  5 13  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 17 14  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 20 22  1  1
 22 29  1  0
 20 23  1  0
 23 24  1  0
 24 30  1  0
 17 25  1  1
 18  2  1  1
  2 26  1  0
 22 27  2  0
 24 28  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 30 34  1  1
 26 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4525407

   ---

Molecule Features

Natural Product: Yes

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: 465.55

Molecular Weight (Monoisotopic): 465.2264

AlogP: 2.63

#Rotatable Bonds: 2

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.58

Np Likeness Score: 1.75

References

1. Li H, Xu D, Sun W, Yang B, Li F, Liu M, Wang J, Xue Y, Hu Z, Zhang Y..  (2019)  HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived Aspergillus versicolor.,  82  (8): [PMID:31390200] [10.1021/acs.jnatprod.9b00183]

Source

Source(1):

• Scientific Literature