boeravinone C

ID: ALA4871580

PubChem CID: 13940643

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(O)c1C)C(=O)[C@@]1(O)c3cccc(O)c3OC[C@@H]1O2

Standard InChI:  InChI=1S/C18H16O7/c1-8-11(23-2)6-12-14(15(8)20)17(21)18(22)9-4-3-5-10(19)16(9)24-7-13(18)25-12/h3-6,13,19-20,22H,7H2,1-2H3/t13-,18+/m0/s1

Standard InChI Key:  ZVSXALWTWGTZSP-SCLBCKFNSA-N

Molfile:  

 
     RDKit          2D

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   28.9924   -4.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9912   -5.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6993   -5.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6975   -3.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4061   -4.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4049   -5.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1111   -5.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1134   -3.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8242   -4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8207   -5.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2388   -4.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5309   -3.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2354   -5.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5247   -5.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5160   -6.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2172   -6.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9286   -6.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9338   -5.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7009   -6.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2832   -5.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2846   -3.9912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2844   -3.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1103   -6.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8127   -6.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8168   -3.5783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.6446   -5.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  3 19  1  0
  2 20  1  0
  1 21  1  0
 21 22  1  0
  7 23  2  0
 10 24  1  1
  9 25  1  6
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871580

   (6aS,12aR)-4,11,12a-trihydroxy-9-methoxy-10-methyl-6,6a-dihydrochromeno[3,4-b]chromen-12-one

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: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 1.64

#Rotatable Bonds: 1

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 2.33

References

1. Sharma VK, Srivedavyasasri R, Ali Z, Zjawiony JK, Ross SA, Ferreira D, Ashpole N, Khan IA..  (2021)  Rotenoids and Other Specialized Metabolites from the Roots of Mirabilis multiflora: Opioid and Cannabinoid Receptor Radioligand Binding Affinities.,  84  (4.0): [PMID:33734684] [10.1021/acs.jnatprod.0c00939]

Source

Source(1):

• Scientific Literature