5-hydroxy-4-((S)-1-hydroxy-2-((1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl)ethyl)furan-2(5H)-one

ID: ALA4751601

PubChem CID: 16115033

Max Phase: Preclinical

Molecular Formula: C20H30O4

Molecular Weight: 334.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CCC[C@@H]2[C@@](C)(C[C@H](O)C3=CC(=O)OC3O)[C@H](C)CC[C@@]12C

Standard InChI:  InChI=1S/C20H30O4/c1-12-6-5-7-16-19(12,3)9-8-13(2)20(16,4)11-15(21)14-10-17(22)24-18(14)23/h6,10,13,15-16,18,21,23H,5,7-9,11H2,1-4H3/t13-,15+,16+,18?,19+,20+/m1/s1

Standard InChI Key:  BNWXVJHFKNLQQH-NLUHLKNCSA-N

Molfile:  

 
     RDKit          2D

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   28.8122  -14.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8122  -15.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5175  -15.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5175  -13.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2227  -14.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2193  -15.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9213  -15.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6314  -15.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6348  -14.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9283  -13.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5183  -16.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2113  -15.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2154  -13.4135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.3447  -13.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6311  -13.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9212  -13.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6253  -12.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6183  -11.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3366  -12.9927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2705  -11.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0112  -10.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1940  -10.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9484  -11.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7079   -9.8627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0502  -11.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
  6 12  1  6
  5 13  1  1
  9 14  1  6
 10 15  1  6
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  2  0
 22 24  2  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4751601

   3-[(1S)-2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2-hydroxy-2H-furan-5-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: 334.46

Molecular Weight (Monoisotopic): 334.2144

AlogP: 3.34

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.58

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 1.63

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: 3.55

References

1. Pu DB,Zhang XJ,Bi DW,Gao JB,Yang Y,Li XL,Lin J,Li XN,Zhang RH,Xiao WL.  (2020)  Callicarpins, Two Classes of Rearranged ent-Clerodane Diterpenoids from Callicarpa Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis.,  83  (7.0): [PMID:32628479] [10.1021/acs.jnatprod.0c00288]

Source

Source(1):

• Scientific Literature