Persicunin F; (3R,5S,8S,9R,10S,13S,15S)-3-hydroxy-15-methoxy-17,18,19,20-tetramethyldecahydro-8H,16H-dispiro[furan-13-furan-9-naphthalene]-7,16(H)-dione

ID: ALA4756932

PubChem CID: 162656306

Max Phase: Preclinical

Molecular Formula: C21H32O6

Molecular Weight: 380.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@H]1C[C@@]2(CC[C@@]3(O2)[C@H](C)C(=O)C[C@H]2C(C)(C)[C@H](O)CC[C@@]23C)C(=O)O1

Standard InChI:  InChI=1S/C21H32O6/c1-12-13(22)10-14-18(2,3)15(23)6-7-19(14,4)21(12)9-8-20(27-21)11-16(25-5)26-17(20)24/h12,14-16,23H,6-11H2,1-5H3/t12-,14+,15-,16+,19+,20+,21-/m1/s1

Standard InChI Key:  ZYNCOAQDKNMIGG-ZXTDIMGXSA-N

Molfile:  

 
     RDKit          2D

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    6.6247   -5.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8788   -4.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -3.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5489   -4.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -5.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -6.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -6.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3738   -5.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0874   -5.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839   -6.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7942   -6.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5126   -6.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5161   -5.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -4.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2342   -5.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2262   -6.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0759   -7.1416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3747   -7.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519   -7.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -6.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7008   -4.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9566   -3.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2898   -3.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6271   -3.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8453   -3.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7387   -3.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3488   -3.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 19  1  0
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  7 21  1  6
  3 22  1  1
 22 23  1  0
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 24 25  1  0
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 25 26  2  0
 23 27  1  6
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756932

   ---

Molecule Features

Natural Product: No

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: 380.48

Molecular Weight (Monoisotopic): 380.2199

AlogP: 2.61

#Rotatable Bonds: 1

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: 2.66

References

1. Alilou M,Marzocco S,Hofer D,Rapa SF,Asadpour R,Schwaiger S,Troppmair J,Stuppner H.  (2020)  Labdane-Type Diterpenes from the Aerial Parts of Rydingia persica: Their Absolute Configurations and Protective Effects on LPS-Induced Inflammation in Keratinocytes.,  83  (8.0): [PMID:32786876] [10.1021/acs.jnatprod.0c00360]

Source

Source(1):

• Scientific Literature