Persicunin E; 13-(11-((3R,5R,10S)-3-hydroxy-4,4,17,20-tetramethyl-7-oxo-1,2,3,4,5,6,7,10-octahydronaphthalen-9-yl)ethyl)-15-methoxyfuran-16(15H)-one

ID: ALA4790385

PubChem CID: 162669083

Max Phase: Preclinical

Molecular Formula: C21H30O5

Molecular Weight: 362.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1C=C(CCC2=C(C)C(=O)C[C@H]3C(C)(C)[C@H](O)CC[C@]23C)C(=O)O1

Standard InChI:  InChI=1S/C21H30O5/c1-12-14(7-6-13-10-18(25-5)26-19(13)24)21(4)9-8-17(23)20(2,3)16(21)11-15(12)22/h10,16-18,23H,6-9,11H2,1-5H3/t16-,17+,18?,21+/m0/s1

Standard InChI Key:  NEJLYDMEHOBZMN-VESXYSOKSA-N

Molfile:  

 
     RDKit          2D

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   12.6334   -7.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3429   -8.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3429   -6.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0523   -7.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0488   -7.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7550   -8.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4691   -7.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4726   -7.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7619   -6.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0450   -6.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1866   -6.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7643   -5.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4773   -5.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4796   -4.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1787   -8.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0408   -8.6919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3437   -9.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6252   -8.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9222   -8.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1448   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8904   -3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0690   -3.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8144   -4.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9216   -4.3663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5900   -2.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9239   -1.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 12  1  0
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  8 16  2  0
  6 17  1  6
  3 18  1  0
  3 19  1  0
  2 20  1  6
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 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790385

   ---

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: 362.47

Molecular Weight (Monoisotopic): 362.2093

AlogP: 3.32

#Rotatable Bonds: 4

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.37

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: 3.35

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