Rhizopycnolide B

ID: ALA3917743

PubChem CID: 134142811

Max Phase: Preclinical

Molecular Formula: C19H20O9

Molecular Weight: 392.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(=O)oc3c(c2c1)[C@@](C)(O)C[C@H](OC)[C@@]31C[C@@H](O)C(=O)O1

Standard InChI:  InChI=1S/C19H20O9/c1-18(24)7-12(26-3)19(6-11(21)16(22)28-19)15-14(18)9-4-8(25-2)5-10(20)13(9)17(23)27-15/h4-5,11-12,20-21,24H,6-7H2,1-3H3/t11-,12+,18+,19+/m1/s1

Standard InChI Key:  DXDVGVFRBGQXNB-GOCROKSSSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   10.7876   -2.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2017   -3.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6133   -2.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2023   -4.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5281   -5.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7765   -6.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6048   -6.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8683   -5.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4961   -3.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4961   -4.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9183   -3.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9131   -4.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6192   -4.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3376   -4.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6298   -3.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3388   -3.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0559   -3.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0694   -2.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3563   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6339   -2.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2883   -6.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0847   -6.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804   -4.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0664   -4.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0489   -4.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7669   -3.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3674   -1.1868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0857   -0.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  8  1  1
  9 10  1  0
  9  2  1  0
 10  4  1  0
  4 12  1  0
 11  2  1  0
 11 12  2  0
 11 15  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 15 16  1  0
 15 20  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  6
  7 22  2  0
 10 23  1  1
 23 24  1  0
 14 25  2  0
 17 26  1  0
 19 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3917743

   ---

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: 392.36

Molecular Weight (Monoisotopic): 392.1107

AlogP: 0.64

#Rotatable Bonds: 2

Polar Surface Area: 135.66

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: 0.37

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 1.89

References

1. Lai D, Wang A, Cao Y, Zhou K, Mao Z, Dong X, Tian J, Xu D, Dai J, Peng Y, Zhou L, Liu Y..  (2016)  Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22.,  79  (8): [PMID:27441892] [10.1021/acs.jnatprod.6b00327]

Source

Source(1):

• Scientific Literature